Charming Accommodations in Stockbridge, MA

Berkshire Vacation Rental: Stockbridge Home Come Experience The Berkshires offers accommodations in Stockbridge, 3.7 miles from Norman Rockwell Museum and 6.9 miles from Cranwell Spa & Golf Club. This vacation home provides air-conditioned accommodations with a patio. Tanglewood Musical Center is 7.1 miles away and Tanglewood is 7.3 miles from the vacation home. With free Wifi, this 3-bedroom vacation home offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. Great Falls is 19 miles from the vacation home, while Canaan Village Historic District is 19 miles from the property. Albany International Airport is 49 miles away.

Pet Friendly • Security/Safety • Parking • Fireplace/Heating • View • Internet • Air Conditioner

The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from the Mass Pike it is an easy commute from Boston or New York City.

The house has 8 foot ceilings and provide a nice 'vacation' like feel with every bedroom but one having its own bath. The common areas are designed for fun and socializing with family and friends.

The 6 fireplaces provide ambiance and a feeling of escape into a time long forgotten. Play a game of pool, chess or checkers with your family. Enjoy two kitchens in which to work from, sit together at the 12 person dining area while enjoy a fire in the large hearth as you drink your wine and soak in the feeling of the Berkshires.

This home has it all and it is designed to give you and your group a relaxing and fulfilling vacation.

Keywords: The Williams House dates to 1797 and has been completely updated in 2010. This home boasts 6 bedrooms, 5.5 baths, two terraces, 6 fireplaces, two full service cook's kitchens, a billiard room, large family room, dining area and table that seats 12 and a lounge/game area. This is the ultimate vacation rental. The house is situated 2 miles from Stockbridge Center, on 4 acres of pristine land with two patios and large grassy areas for outdoor fun. Enjoy all that the Berkshires offer while staying in luxury with your family and friends.

- "This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely recommend!" - "Enjoyed our stay for a girls weekend. Big house, well kept up, with nice bedrooms and bathrooms, lots of places for us to hang out. Close to lots of things in the berkshires. Would definitely stay again."

Too Good AKA 2 Goodrich St is located in Stockbridge, just 19 miles from Great Falls and 19 miles from Canaan Village Historic District. The property is around 6.4 miles from Cranwell Spa & Golf Club, 6.6 miles from Tanglewood Musical Center, and 6.7 miles from Tanglewood. Free Wifi is available throughout the property and Norman Rockwell Museum is 3.2 miles away. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher, and 3 bathrooms with a bath and a hair dryer. A TV with satellite channels is offered. The accommodation is non-smoking. Guests can relax in the garden at the property. Haystack Mountain State Park is 25 miles from the vacation home, while Holley Williams House Museum is 25 miles from the property. Albany International Airport is 49 miles away.

Barbecue/Outdoor Cooking • Fireplace/Heating • Child Friendly • View • Other • Security/Safety • Internet • Air Conditioner

Bed & breakfast in Lee with free breakfast and a 24-hour fitness center
An outdoor pool, a 24-hour fitness center, and spa services are available at this smoke-free bed & breakfast. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a microwave in a common area, a refrigerator in a common area, and a seasonal outdoor pool are onsite.
The Inn at Stockbridge offers 14 air-conditioned accommodations with designer toiletries and hair dryers. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Flat-screen televisions come with cable channels.

This Lee bed & breakfast provides complimentary wired and wireless Internet access. Additionally, rooms include irons/ironing boards and complimentary toiletries. Housekeeping is provided daily.

- "Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts. The new owners have added new touches to this Inn and the pride of ownership shows. Highly recommended 👌 " - "Fantastic!" - "Well-run and elegant property. " - "We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"

7 miles from Cranwell Spa & Golf Club in Stockbridge, Stockbridge Retreat with Pool and Hot Tub! features accommodations with access to a hot tub. The air-conditioned accommodation is 3.8 miles from Norman Rockwell Museum. There's an outdoor pool and guests have access to free Wifi and parking on-site. Featuring a patio and garden views, the spacious vacation home includes 4 bedrooms, 4 living rooms, cable flat-screen TV, an equipped kitchen, and 4 bathrooms with a hot tub and a bath. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood Musical Center is 7.1 miles from the vacation home, while Tanglewood is 7.3 miles from the property. Albany International Airport is 49 miles away.

Internet • Security/Safety • Accessibility • Hot Tub • Fireplace/Heating • Guest Services • Pool • Oceanfront • Ocean View • Other • Parking • View

Bed & breakfast in Stockbridge with free breakfast and a steam room
A steam room, a garden, and barbecue grills are available at this smoke-free bed & breakfast. Free continental breakfast and free self parking are also provided. Other amenities include a picnic area.
Housekeeping is available on request.
Tanglewood Suites offers 2 air-conditioned accommodations with DVD players and coffee/tea makers. Beds feature premium bedding. Refrigerators and microwaves are provided. Bathrooms include showers, complimentary toiletries, and hair dryers.

This Stockbridge bed & breakfast provides complimentary wireless Internet access. Flat-screen televisions are featured in guestrooms. A nightly turndown service is provided and housekeeping is offered on request.

- "Bed was quite comfortable and the setting was in a beautiful neighborhood. Excellent proximity to Tanglewood. And host gave exceptional information regarding local eateries and things to do. I would have liked to have known at booking that the owner does not accept credit (as the hotels.com app allows for the appearance of down payment by credit). All was well resolved at time of arrival but more accurate information on the description at booking would be helpful and clarifying. Also this is more of a private room rental than hotel stay. Also well and good, though again, accurate representation via hotels.com description should make this more clear. All in all a good stay and would recommend for anyone seeking a very close stay for Tanglewood performances. "

Situated on two acres of hills and forest, this Stockbridge B&B offers free Wi-Fi, free breakfast and stunning views of the surrounding Berkshire mountains. The Stockbridge town centre is just 2 km away. Each suite at The Cottage features a cable TV and a seating area with a sofa, as well as a small refrigerator, microwave and coffee maker. En suite bathrooms include free toiletries. Guests are provided with a private entrance to their suite as well as an outdoor patio with a dining area. An on-site terrace and garden offers another spot to relax.Mount Greylock is 45 km from The Cottage. The Norman Rockwell Museum and Stockbridge Golf Club are within 3 km from The Cottage, which is just 3 minutes’ drive from the site of the Tanglewood Music Festival. Butternut Ski Resort and Bousquet Ski Area are both less than 16 km away, while Jiminy Peak Mountain Resort is 38.3 km away.

Parking • Air Conditioner • Private Beach • View • Balcony/Terrace • Breakfast • Oceanfront • Wheelchair Accessible • Smoking • Ocean View • Pet Friendly • Kitchen

Within walking distance to Main Street in Stockbridge, 38 Church St. offers a large backyard and gardens which boarder preservation land and views of Naumkeag! Freshly furnished open floorpan with all amenities including a fully outfitted kitchen, gas-grill, private terrace with outdoor furniture, and indoor sauna. Steps away from hiking, shopping, gardens, tennis courts, golf club, museums, skiing, and the local coffee shop; this house is the ideal locale for you to unplug and plug in to everything that the Berkshires has to offer. 8 minute drive to Tanglewood!

Other • Spa • Barbecue/Outdoor Cooking • Guest Services • Bedding/Linens • Wellness Facilities • Tv • Internet • Laundry • Fireplace/Heating • Security/Safety • Air Conditioner

Cozy Stockbridge Cabin - Walk to Beach and Lake! is located in Stockbridge, just 23 miles from Great Falls and 23 miles from Canaan Village Historic District. The property is around 3.1 miles from Tanglewood, 3.2 miles from Norman Rockwell Museum, and 5 miles from Cranwell Spa & Golf Club. Free Wifi is available throughout the property and Tanglewood Musical Center is 2.9 miles away. The air-conditioned vacation home consists of 2 bedrooms, 2 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a shower. Guests can enjoy a meal on an outdoor dining area while overlooking the sea views. For added privacy, the accommodation features a private entrance. Haystack Mountain State Park is 28 miles from the vacation home, while Holley Williams House Museum is 29 miles away. Albany International Airport is 48 miles from the property.

Internet • Accessibility • Oceanfront • Child Friendly • Spa • Other • View • Sports/Activities • Guest Services • Ocean View • Security/Safety • Parking

The Taggart House is an grand estate in the heart of The Berkshires. The property is a 5-minute walk to the center of Stockbridge, yet quietly situated on 3 manicured acres along the Housatonic River. The Taggart House was constructed in 1850 by noted Stockbridge resident Henry Dwight Sedgwick. Recently added to the National Register of Historic Places, the Taggart House combines fine 19th century architecture with luxurious comfort and modern amenities.

- "My family had a reunion of sorts at the Taggart house and our stay and the accommodations at the Taggart house were just wonderful. We congregated in the kitchen to make meals, we had dinner in the dining room, we worked on a puzzle by one of the fireplaces, and we watched family slides on the big TV in the family room. We had a very short walk to the Red Lion Inn/downtown and we had a 10 minute drive to Tanglewood. We highly recommend Taggart house to anyone looking to feel at home with their family & friends in the Berkshires, and we hope to stay here again in the future."

2 Mi to Norman Rockwell Museum Stockbridge Apt! offers accommodations in Stockbridge, 5.7 miles from Tanglewood Musical Center and 5.9 miles from Tanglewood. This apartment provides accommodations with a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 2.4 miles away. The air-conditioned apartment is composed of 1 separate bedroom, a fully equipped kitchen with an oven and a microwave, and 1 bathroom. Towels and bed linen are provided in the apartment. The property has an outdoor dining area. Cranwell Spa & Golf Club is 6.1 miles from the apartment, while Great Falls is 20 miles away. Albany International Airport is 46 miles from the property.

Other • Security/Safety • Fireplace/Heating • Accessibility • Pet Friendly • Parking • Internet • Child Friendly

Summary:
"Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved and we think you will too! There are ash hardwood floors, custom white pine trim and mahogany decks. The interior has an open-concept floor plan inviting abundant natural light.

Guests must agree to a rental contract prior to booking."

The Space:
"The house is perfectly located in the center of the Berkshires. It is no more than 10 minutes from Lenox, Lee, West Stockbridge and Great Barrington. Central heating and air conditioning as well as other great features. Guest access to near by swimming, skiing, apple picking, fall foliage views, hiking, theater, and great restaurants. I live near by and I am happy to assist any time there are questions. My Dad is retired in the area and is also available to help. There is a sidewalk in front of the house that goes to town. The neighborhood is great for walking, jogging, or bike riding."

Guest Access:
Check in anytime after 3PM.

Other Things to Note:
Spring is an awesome time of the year in the Berkshires. However, we do not see high demand and so the prices are great!

- "There was ample room for 7 of us, including a two-year-old. There were spaces to sit and eat together, and spaces for privacy. The hosts put out a child's table and chairs and an indoor play tent that amused our toddler. We scarcely needed to call on our hosts for assistance, but they were instantly responsive. The location is a two-minute drive to the Red Lion, and easily accessible to Lenox and Great Barrington." - "The property was clean and very, very comfortable. Rooms were adequate for three of the four couples staying. The one room that was a minor challenge was a room that appeared to be child friendly. Great kitchen, adequate eating area and social common areas. Surrounding property grounds afforded able space for outdoor activities. Location to Sturbridge and western Massachusetts and surrounding states was a definite advantage."

Steps to Downtown Stockbridge Home with Patio! offers accommodations in Stockbridge, 5.7 miles from Tanglewood Musical Center and 5.9 miles from Tanglewood. Guests staying at this vacation home have access to a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 2.3 miles away. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Cranwell Spa & Golf Club is 6.1 miles from the vacation home, while Great Falls is 20 miles away. Albany International Airport is 46 miles from the property.

Accessibility • Security/Safety • Sports/Activities • Internet • Child Friendly • Pet Friendly • Other • Fireplace/Heating • Parking

Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park and tennis courts within a 5-minute walk. Lake rights to the Stockbridge Bowl, Weber grill and Solo firepit.
The home of Norman Rockwell, Stockbridge is the quintessential Berkshire village.
Foosball table and dart board, plus yoga mats are available for your enjoyment.

- "We stayed in this house for a wedding weekend with family. The location was perfect for touring the area around when we weren't busy with wedding festivities. Nice fenced-in backyard with a view, which we didn't get to experience because we ran out of time. But there is a nice spot to have tea inside by the windows looking out. The house came well appointed with necessities. The cleaning people were no shows for the owners who did their best scrambling around to get the house ready for us. Such nice people! It was great to have the option of ceiling fan or air conditioning. The beds were very comfortable. We didn't do any cooking so can't attest to the kitchen equipment. So nice to be able to walk into the town of Stockbridge which was very cute. We all enjoyed our stay."

The Front 5 Bedroom Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & outside gas grill on the main level. Upstairs are 5 bedrooms - Two Queen Bedrooms & One Full Bedroom share a large hallway bathroom. One Queen Bedroom has its own bathroom & one bedroom with two full beds has its own bathroom. House Sleeps 11 guests per town by-laws. $700 per night.

The Back 6 Bedroom House offers large fully stocked eat-in kitchen, oversized great room, large dining room, screened porch, side deck & outside gas grill. A brand new fully accessible ADA Compliant Handicap 1st floor Queen Bedroom with private bath - roll-in shower, folding seat in shower, handicap toilet and sink. 2 King Suites upstairs with new private baths. Three other bedrooms with Queen Beds share one newly renovated hallway bathroom. House sleeps a maximum of 13 guests per town bylaws. New natural gas furnace. Nightly rate is $850 per night.

The booking on this site is for the front 5 Bedroom house only $700 per night. If you would like to book just the 6 Bedroom House only $850 per night or to book the entire 11 Bedrooms $1550 per night please message me and I will update your booking quote.

Our home is a No smoking of any kind inside & on property grounds. We do allow dogs at $150 per dog per stay. No cats.

Our Victorian is centrally located, an easy one block stroll to Norman Rockwell's Main Street Red Lion Inn, Restaurants, Shopping and Berkshire Theatre, Tanglewood, Jacobs Pillow, Stockbridge Theatre.
3.5 miles to Swim, Fish, Kayak, relax on the Town Beach on Stockbridge Bowl. Ski Butternut, Catamount, Bousquet, Jiminy Peak.

- "Perfect for a large group, this historical home is nicely kept." - "Our family had a fabulous stay in Stockbridge. The house was perfect for all 11 of us, 3 generations: a well stocked kitchen, a working gas grill, a careokee setup, a short walk to the town, and a wonderful comfy living room. We were close to the major sites in the area, especially the Norman Rockwell Museum." - "We made wonderful memories in this home in Stockbridge. Great location in a great town! Walking distance to parks, food and the Main Street of Stockbridge! Sue was very responsive, easy to work with and very accommodating! House was spacious and loved the many bedrooms and bathrooms!.look forward to many returns."

Summary:
Beautifully renovated three bedroom in Stockbridge with a great layout and energy throughout the home. In addition to the large and very pretty screened in porch, there is a newly created area off the back that has pavers with a modern fire pit, a new Weber Genesis grill and four wood and wicker chairs - a great area to relax. Clean, updated and cozy all at once.

The Space:
Living room is inviting and nicely decorated. There is plenty of seating for all with a comfy couch and ottoman (that can be used to make a chaise at one end of the couch) and two swivel chairs.The large 55 inch tv has basic cable and a roku for sound and streaming apps such as Netflix, Hulu, Amazon Prime, etc with your log in information. Original artwork can be found all around the home, along with some framed vintage posters.

Very nice flow and layout in the kitchen; easy to use with updated appliances and well equipped; leads right to the dining area inside or the lovely screened in porch outside that has a lovely teak round dining table. Large galley kitchen with a gas stove, new appliances and lots of white quartz counter space, perfect for large meals for the whole crew. New dishwasher to make cleaning a breeze. Essentials including microwave, drip coffee maker, toaster and kettle available for use.

Well stocked kitchen with all the necessary cooking/serving items including cookware, pots, pans, plates, bowls, glasses, mugs, silverware and even children's dinnerware.

The dining room has round table seating for eight with the table leaf. There is space for two at the kitchen island. An additional table with chairs is located in the large screened in porch.

There are a total of three bedrooms to accommodate guests during your stay, for easy planning here are the bedroom layouts:
Bedroom 1: master with king bed, dresser, desk, full length mirror, en suite bathroom and small walk in closet
Bedroom 2: queen size bed
Bedroom 3: single day bed with another single pull out trundle bed

There are two full size bathrooms. The en suite in the master has a large walk in shower with tile and marble shelves; there is one vanity with drawers and counter space and a large mirror and a medicine cabinet with mirror on the side of the vanity.

Seamless indoor outdoor living including, screened in porch with round teak dining table,; peaceful back yard, fire pit with plenty of seating and a new Weber Genesis grill.

Other things to get excited about:
-Only four small steps up to the front door of this one floor home, perfect for guests with limited mobility.
-Hardwood floors throughout the home and tile floors in bathrooms.
-Washer and dryer with plenty of detergent and dryer sheets
-There are two AC splits: one in the living room and one in the master
- Parking for two cars in the driveway and street parking is available
-Bring your furry friends, up to two dogs allowed, $50 per dog, must be at least 1 year old, sorry no puppies!

Guest Access:
Everything you need for a great stay, toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!

The Neighborhood:
Food and Drink favorites:
Red Lion Inn, Stockbridge
Once Upon a Table, Stockbridge
The Lost Lamb, Stockbridge
Bistro Zinc, Lenox
Amici, West Stockbridge
Four Brothers Pizza, Great Barrington
Aegean Breeze, Great Barrington
Zichotencati, Great Barrington
Cafe Adam, Great Barrington
Naji’s, Great Barrington
Marketplace Kitchen Table, Great Barrington
Great Barrington Brewery

Culture and Wellness :
Jacob’s Pillow, Dance
Shakespeare and Company
Tanglewood
Kripalu Center for Yoga and Health
Miraval Berkshires Resort & Spa
Shaker Mill Books
Tanglewood
Downtown Lenox
Berkshire Botanical Garden
Naumkeg
Chesterwood
Norman Rockwell Museum
The Mount, Edith Wharton’s Estate
Herman Mellville’s Arrowhead

Skiing, Snowboarding and tubing:
Butternut Ski Area and Tubing Center
Catamount Mountain Resort

Lakes: Close to public lakes for swimming, kayaking, fishing or lounging by the water:
Card Pond
Lake Mansfield
Lake Garfield
Benedict Pond
Umpachene Falls
Lake Onota

Hiking:
Monument Mountain
Housatonic Flats
October Mountain State Forest
Beartown State Forest
Tyringham Cobble
Ashintully Gardens
Housatonic Flats

Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no smoking, no partying, and being respectful of the neighbors apply.
Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!

No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

Pets: Damage caused by pets is not covered by the accidental damage waiver.

- "The weather was humid and unpleasant, which served to increase our appreciation for this lovely home, since we ended up staying inside for much of our trip! Would absolutely return—thank you to our hosts!!" - "This property is pristine, perfectly decorated and appointed. It has been renovated very nicely. The beds are comfortable and the many towels are large and fluffy. We visited during a hot summer week. Although there are two mini splits in the main bedroom and kitchen area, the other two bedrooms are uncooled and very hot. Visitors should also be aware that there are no Ubers in the Berkshires!! We would stay in this property again, but maybe in the cooler weather."

Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to ensure its availability!

Beautifully restored 1913 home features 3-season front porch for entertaining or relaxing, steps from Laurel Hill Assn preserve, and has ‘secret gardens’ where you can stroll through paths and see our fruit, veggies & flowers tended by our gardener in Spring and Summer. We have a fire pit for guests to sit around in the evenings, a lighted outdoor dining area and pergola, all situated steps from the footbridge leading to Ice Glen Trail. This amazing location is also a short stroll from Historic downtown Stockbridge where you will find plenty of bakery & coffee shops, gifts, sweets, bars and dining.

The house has heating & air-conditioning, a dedicated office, laundry room and 3 bedrooms, including:
Master Bedroom (White Room)- This en suite room has a highly-desirable King-sized bed, private bathroom w shower and skylight, plenty of closet space, and view of the river(seasonal);
Queen bedroom (Blue Room) - This room has a Queen bed, closet, and is next to the 2nd fl full bathroom with bathtub, shower & shaving mirror;
Full & Twin bedroom (Khaki & Green Room) - This room is suitable for adults with children, as it has a Full bed & a Twin-sized Day bed with a bureau and view of the gardens and river (seasonal). It is next to the laundry room and across the hall from the full bathroom with tub/shower.

House has a fully-stocked Kitchen with new gas range, dishwasher, microwave, Keurig machine, drip coffeemaker, bean grinder, teapot, cookware, wine bottle opener, utensils, china, glassware, spice collection. On the back porch, there is a smoker if you enjoy outdoor slow-cooked dinners.

We are a short drive to Tanglewood, Berkshire Theatre Festival, Norman Rockwell Museum, Naumkeag, Kripalu Wellness Retreat, Chesterwood, Stockbridge Golf Club, local ski resorts (Butternut and Bousquet) & neighboring towns Gt Barrington and Lenox with many restaurants, bars, and shops to experience!

- "Julie’s home is a wonderful base for exploring all the Berkshires have to offer, and then returning to a special, comfortable, incredibly convenient home away from home. Being able to walk to Stockbridge Main Street, or hike the Ice Glen trail, or quickly come home after hearing a glorious concert at Tanglewood—this special home offers all that snd more. We look forward to returning in the years ahead! Absolutely 5 stars!!" - "Fabulous!"

Welcome to "The Hideaway On Main " in Stockbridge Center.
Our recently renovated 2 bedroom unit offers a clean mix of modern elegance and cottage charm. With a private rear entrance and a charmingly modern ambiance full of delightful surprises, you will feel like you have been transported to a secret Hideaway.

Our rental is perfect for 2-4 people. Please Note:
We have a strict No Pets, No Smoking policy!

Please watch our VIDEO TOUR of the property. Find it in the third position of the photo gallery. If you are having trouble finding it please message me.

The Hideaway on Main Highlights Include:

BEDROOMS-

*Best sleep of your life "Purple" queen mattress in the rear bedroom--plush feel.
*Decadent cool gel memory foam Novafirm King mattress in the front bedroom--medium to firm feel.
*Cozy 100% cotton bathrobes to enjoy while you are our guest.
*100% cotton sheets and bedding washed in **UNscented detergent, all you will smell is 'Clean' !
*Wood headboard panels that are wiped and cleaned between guests.

KITCHEN-

* A Gaggia Brerra Italian espresso & coffee machine for making truly delicious coffee. Tea pot, fancy tea cups, an assortment of tea bags and loose tea are also available.
*All new stainless steel appliances: easy clean glass top stove including oven with air fry & convection, dishwasher, disposal, microwave, digital hood vent and full size refrigerator/freezer.
*Full set of Cuisinart Pro Series stainless steel pans. One non-stick omelet pan.
*Lobster Pot, mixers, blender, toaster, rice cooker, crock pot, pizza pan, cookie sheet, glass baking dishes of various sizes, an electric kettle, thermal carafe, glass mixing/serving bowls with covers, huge cutting board work surface, platters, potato masher, spices, oil and vinegar, sugar/sugar substitute.
--Photos available of all kitchen supplies, just ask us : )
*We have an abundant supply of dishes, glasses and flatware ( no need to wash a dish every time you use it because you we have more than four).
*Picnic gear: melamine plates, bowls, cups, cooler, and folding chairs to lend.

A DEDICATED WORK AREA-
Whether you are a digital nomad or just needing to scroll through your emails, you will enjoy the office area located in a separate space from the living room which features:
*A SIT-to-STAND desk/ Herman Miller AERON desk chair/HP Monitor on swing arm/basic stationary supplies (ask for specifics), keyboard, power hub/usb ports ON the desk surface, tack board, ipad stand, swing arm task light and abundant natural light.
Note: if you are making zoom calls, the door can be closed off from the rest of the unit for privacy.

BATHROOM-
Our luxurious shower has both a Huge Rainfall Shower Head and Handheld shower. You will find shelves and cubbies for toiletry bags or personal items, 5 hooks for towels or clothes, a stool to dry off your feet, great lighting with two magnification mirrors (one stationary and one for a second person to use in another area), and an assortment of extra toiletries in case you have forgotten something. A hair dryer is located under the vanity and clothes hampers are in each bedroom.
* "SCENT SENSITIVE” products are available and include unscented shampoo, body wash, hand soap, dish soap, moisturizers, and natural cleaning products. Look for the cobalt bottles throughout the unit.
We never use dryer sheets or air fresheners. We believe the smell of clean is better than heavy perfumes.

LIVING/DINING ROOM-
Our center room functions perfectly as a dividing area between the bedrooms to create a sense of privacy in each room and a very functional living room and dining area with:
*Knoll Bertoia Chairs around an elliptical wood dining table.
*Our incredibly comfortable hanging egg chair--grab a blanket & a book to enjoy the morning lost in a favorite read.
*The corner sectional is extremely comfortable for four people and has a reading light near the chimney. It is a great place to watch a movie or set up a game for game night.
*A collection of books, magazines, puzzles, games, intricate coloring books with colored pencils and a Ukulele are available for your use while here.
*You will find many beautiful items from Pine Cone Hill/Annie Selke/Dash and Albert: rugs, bedding, curtains, tile, and throw pillows are all over the unit.

OUTDOOR SPACE-
You will have exclusive use of the rear deck including the patio table and chairs and shared use of the rear yard and fire pit area. Then all of the Berkshires is beyond…
Ask us about our favorite hikes, ponds, and vistas.

The AREA-
We are close to everything in the village--just a short walk to fresh chocolate croissants, gourmet treats for your picnic basket at Nejaime’s Wine Cellars, an ice cream from Main Street Cafe, dinner at Once Upon a Table, live theater at the The Unicorn Theatre, or a visit to historic Mission House or the Sedgewick Pie.
We are centrally located in the Berkshires with easy access to north and south counties near cultural attractions of all kinds, four ski areas and hundreds of hiking trails within 15 minutes driving time. Tanglewood, Kripalu and Shakespeare & Company are all just ten minutes away.
This vacation rental is located on the first floor (not basement) of our vacation home, our unit is on the second floor (each unit has a private entrance). We are available for help with restaurant and sightseeing suggestions or with any emergencies. We also have a local property manager available when needed if we aren't available.
The amount of interaction with us will be up to the guest.

Please note: We have exterior entry Blink doorbell cameras for your convenience and general preventative security. If you are having difficulty opening the door lock or forget your code, simply buzz the bell and it will call my cell phone. I can identify who is buzzing and remotely open the door for you. This is our second home and we are often in the second floor apartment. We will not be intrusive, but we are happy to offer suggestions for restaurants or to lend equipment if needed.
There are three areas with steps within the unit. One step in the bathroom, two steps from the rear bedroom to the living room, and one step from the kitchen to the living room.

- "Perfect location, close to museums, great restaurants, music everywhere and owner of this property has thought of everything." - "What an amazing stay!! My sister and I took our mom on a trip to the Berkshires for her 70th birthday and we used the Hideaway on Main as our home base. It is such a cute place and centrally located to many adventures. Lots to do and see so close to the house! The owner Christine could NOT have been nicer. She was very communicative and wanted to make sure we had everything we needed for the perfect birthday weekend. And we sure did! The house was extremely well stocked - there were more amenities and supplies then you could possibly ask for. We felt very welcomed from the second we arrived. We would definitely stay here again. I can't recommend the place enough. Thank you Christine!!"

This gorgeous farmhouse has four bedrooms each with a private full bathroom. Each bedroom has a queen size bed, sitting chair and closet or armoire .There is a fully stocked kitchen, living room with fireplace and dining room that seats 8 people. Three bedrooms are on the second floor and each has a split unit to control heat and air conditioning. There are extra sheets and towels, a washing machine and dryer and ample parking. We have an inground swimming pool ( swim at your own risk) heated during July and august. There is beautiful outdoor furniture situated on the grounds, surrounded by flower beds and lovely scenery. Minimum stay September-June is two nights. July-August minimum stay is 5 nights. Near family friendly ski mountains catamount, butternut and 30 minutes to jiminy ski resort. Golf, Lenox pickleball and tennis courts, yoga and Maravel spa nearby. Fifteen minutes to major summer activities such as Tanglewood and Jacobs Pillow.
The owner has a full apartment downstairs on the side with a private entrance and may be present on the property at various times.

- "We had the best time staying at this special home. We came with another couple and each had 1 1/2 year olds. It was the perfect house, the pool and property were perfect for family fun. Our kids had the best time!" - "Had a wonderful stay. The fact that each bedroom has its own bathroom is a real plus. House is also conveniently located near Tanglewood and Jacob's Pillow. The saltwater pool is very nice and was really well utilized during our stay. And Rhona was very easy to deal with and made sure that we had a good experience."

This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red Lion Inn, the public tennis
court, while providing a sense of privacy and serenity from its backyard views to the Berkshire Hills across flower-filled mature plantings. It is easy walking distance to the Berkshire Theater Festival, the Red Lion Inn, and only short drive to Tanglewood, the Norman Rockwell Museum, and the the Berkshire Botanical Garden. Walk down
the sloping lawn to the banks of the Housatonic and listen to the breeze in the trees while taking in the scent of mountain air. When the weather's fair, sit out on the terrace with friends for dinner and watch the stars.
The kitchen has all new appliances, fully supplied for the ambitious chef.

Cozy up in the living room or enjoy playing the baby grand Yamaha piano.
One bedroom offers a full canopy bed, and the larger bedroom has 2 twin beds. It's blissfully quiet at night.
[Folks, this is Main Street and there is traffic sound in the daytime, but the vast majority of guests have found it very livable.]

The small upstairs sitting room has cable TV but you might prefer to just read a book or write at the window with a sweeping view to the hills over the treetops. There are two full bathrooms, one on each floor.

We welcome you to enjoy the farmhouse for a memorable stay with your friends or family.

- "We were looking for a “home base” for rest and relaxation and in close proximity to the Appalachian Trail for some day hiking. Claudia’s place did not disappoint! The house is comfortably appointed, super quaint, and perfectly situated for local activities and dining options. The town of Stockbridge is a quick walk away and offers a wonderful bakery, the Red Lion Inn, and a few shops. Very magical. Claudia was very responsive and ensured we had all we needed for a terrific and private get-away. We really had a wonderful time and look forward to returning in summer or fall!"

Refurbished cottage, perfect for a couples getaway. This retreat is tastefully decorated with with local antiques & fresh linens. Nestled into the forest in the best possible location, just one mile from Tanglewood and an 5 minute walk to Stockbridge Beach. Lots of places to put your feet up with a good book, or just enjoy the sound of the wind in the trees. This is a "seasonal camp" with a/c in the bedrooms. You can also expect an occasionally visit by a local bear, chipmunk or red wing hawk.

We encourage our guests to follow local orders regarding COVID. Information can be found on the Town of Stockbridge website. Feel free to ask what we do to keep the cottage clean for you.

- "A most helpful owner made any bumps imperceptible. The area is a jewel and the cabin provides an excellent base for the Berkshires" - "This rustic property had loads of charm and an excellent location in the heart of the Berkshires. A perfect size for the two of us, in a quiet semi rural neighborhood. Just minutes from the town beach, and many great destinations in the Stockbridge and Lenox area. Great for relaxation, and a definite feeling of a summer camp property. The host was very helpful."

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop, a grand party or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

Villa Favorita is ideal for a large extended family, with 6 bedrooms that can comfortably sleep couples with multiple children, and 5 bedrooms comfortable for couples or individuals.

Five large rooms on the first floor are homey and rich in historic detail. The dining room with large French doors is joined to the modern kitchen through the butler’s pantry. The utility room has a new washer and dryer and a half bath. The living room with built-in bookshelves opens into a spacious front hall with a grand piano and a harpsichord. The first floor also has a comfortable wheelchair-accessible bedroom with handicap shower.

The second floor has five enormous bedrooms overlooking fields and forests; three of these are master bedrooms with en suite baths, and the dimensions of all but one are over 220 square feet.

The third floor, originally servants' quarters, has one shared bath and five more bedrooms, two approaching the size of the master bedrooms, and one that can double as a quiet study with desk and flat-panel monitor.

- "This is a home that loves to be filled with family. There is ample space for hanging out, recreation, and conversation. The kitchen is welcoming and well stocked for cooking for many or just a few. There are spacious bedrooms and many with their own or a shared bathroom which makes accomodations comfortable. There are also sleeping spaces on the ground floor for those who may have difficulty with stairs. With a well stocked library, a small pool, a most excellent ping pong table and many musical instruments, it is a home where any groups can enjoy time together, and still have beautiful spaces for solitude and quiet contemplation. The grounds are lovely and worthy of exploration. Not modern, the house has the gracious air of a home that was built well, and meant to give space to create happy memories for ages. Grateful for our stay and to the hosts for sharing this home with us and others."

Enjoy our new in-town stylish pied-à-terre , a block from the Red Lion. Off the main thoroughfare just enough but an easy walk for a cocktail on the porch! a stand alone building, large open window filled living/kitchen area, small 2nd floor balcony with chairs to relax, spacious bdrm with king size bed, and a modern tiled bathroom. Central HVAC, great water pressure, all new everything and a well appointed kitchen. July and August are by the week rental only.

- "Clean, felt new, can walk to center in minutes, very nice accomodations." - "Thoroughly enjoyed everything about this property. It is steps to the Red Lion Inn though away from any traffic noise. The apartment is furnished in a mid century modern style. The kitchen is well equipped. The living room is light and airy enveloped by large windows. The king bed is firm and quite comfortable. One could spend hours in the shower. Our dogs can’t wait to come back. Many thanks to Linda for getting everything write."

Hello hip, glamping cabin! Our 2 bedroom 1.5 bath cottage has been fully remodeled. The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. The cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights and half bath or put on a favorite record. Kids will love the cozy sleeping loft. A 8-10 minute stroll or 2 minute drive to the lake public beach (The lovely Stockbridge Bowl) Outdoor shower. Weber gas BBQ grill. 6 minutes to Tanglewood and Lenox downtown.

- "We had such a great stay. As advertised, the place is compact but there has been so much attention put into every detail that everything is comfortable, functional and aesthetically pleasing. Wonderful location close to all the things you could want to do in the area but it's also in a lovely, quiet neighborhood adding to its homey-ness. We would love to return!" - "Had a wonderful weekend at the cottage for a college roommates "reunion" weekend. Everything was nicely updated and spotlessly clean. It was a hot weekend and the A/C worked great. Easy to get to Lenox for dinner, great hiking nearby, and a lovely place to relax and catch up. Highly recommend."

My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic river, and the oldest preserve in Massachusetts - the neighborhood, the ambiance, the comfy beds, the light, the outdoors space. My place is good for couples, solo adventurers, business travelers, and families (with kids). The place is newly renovated.

- "This house was the perfect home base to explore the best of what the Berkshires has to offer--Tanglewood, Shakespeare and company, the Mount, the Clark, Mass MoCA, and great hiking. The space really felt like home, with a wonderful kitchen and dining areas, and an abundance of cozy reading areas from which to choose. Amazing windows and light made it a wonderful place to spend time. Perhaps best of all was the host, Joanna, who made the whole check in/check out process incredibly easy, and made us feel immediately at home. Book early for this home away from home!"

Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake activities, Tanglewood, the Norman Rockwell Museum, and hiking trails - all found within a short drive. Ease into your mornings with a good book and a steamy cup of coffee on the private porch, and later, walk to the lake for a picnic!

-- THE PROPERTY --

C0077602830 | Free WiFi | Expansive Deck | Sunroom

Indulge in a leisurely Berkshires lifestyle when you stay at this cozy, light-filled cabin. Ideal for pairs of two looking to escape modern distractions and spend time in nature.

Bedroom 1: King Bed | Bedroom 2: 2 Twin Beds (Photos Coming Soon) | Sunroom (Not Private): Twin Bed w/ Twin Trundle Bed

OUTDOOR LIVING: Large deck w/ outdoor dining table, lounge chairs, gas grill, 2 kayaks, 2 stand up paddleboards, beach chairs, outdoor shower, walk to lakeshore, neighbors nearby (please be respectful of the noise level outside)
INDOOR LIVING: Vaulted ceilings, open layout, high-top counter seating, desk, ample natural light, bright interior, flat-screen Smart TV (no cable), 2 cozy bedrooms, 2 full baths, 800 square feet total
KITCHEN: Well equipped, dishwasher, gas range stove, toaster oven, microwave, drip coffee maker, cooking basics, dishware, flatware, pots, pans
GENERAL: Linens/towels, window air conditioning, first aid kit, Pack 'n Play, washer/dryer, wall heaters, space heaters, ceiling fans
PARKING: Driveway (3 vehicles max)

This charming seasonal cottage dates back to the 1940s. It still maintains much of its original details and rustic charm, which is balanced nicely by its freshly whitewashed interior, comfortable amenities, welcoming decor, and brand new cedar outdoor shower.

Thoughtful touches like picnic blankets, beach towels, and even a record player and albums make this cute cabin an easy place to call home during your Berkshire vacation.

Situated at the edge of the woods on a shared, dead-end drive, the cottage offers the perfect place to get away (and possibly even see some wildlife!) while being just minutes from Lenox and Stockbridge and walking distance to the lake beach. And, when the wind is just right, you can even hear the faint sounds of Tanglewood's music drifting across the lake on a warm summer night.

Note from the owner: We have so many happy memories at 'Elandee,' named after our two daughters, L and E. We hope that if you choose to stay, you have an enjoyable and memorable time here, too!

-- THE LOCATION --

STOCKBRIDGE BOWL: Stockbridge Town Beach (0.1 miles - 5-min. walk), BSO Beach (2.3 miles), Stockbridge Bowl Boat Ramp (3.1 miles), boating, swimming, fishing, kayaking, paddle boarding, canoeing
HIKING: Brothers Trail (3.2 miles), Parsons Marsh Reserve (3.4 miles), Olivia's Overlook (3.8 miles), Burbank Trail (3.8 miles), Stevens Glen Trail Head (4.5 miles), Monument Mountian Reservation (6.2 miles), Appalachian Trail (11.6 miles)
LOCAL ATTRACTIONS: Orleton Farm (0.9 miles), Koussevitzky Music Shed (1.9 miles), Seiji Ozawa Hall (2.0 miles), Frelinghuysen Morris House & Studio (2.0 miles), Tanglewood (2.5 miles), Ventfort Hall Mansion and Gilded Age (3.4 miles), Norman Rockwell Museum (3.8 miles), The Mount, Edith Wharton's Home (4.4 miles), Cranwell Mansion (4.7 miles), The Playhouse (5.5 miles)
SKIING: Ski Butternut (11.3 miles), Catamount Mountain Resort (18.0 miles), Jiminy Peak Mountain Resort (25.4 miles)
AIRPORT: Albany International Airport (51.5 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This property is best suited for 4 guests, but can sleep a total of 6 with the use of the non-private sunroom
- NOTE: This property is not suitable for children under 12
- NOTE: Your safety matters. This property features 2 exterior security cameras, above the front door and the deck, all facing outward. They do not look into interior spaces

- "Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm" - "Cant say enough nice things about our stay at this cabin. We traveled from MO to see James Taylor at Tanglewood over the 4th of July weekend. We stayed 4 nights, and had the time of our lives. The first few nights my wife and I stayed by ourselves, and explored Lenox and the neighboring towns. Lots of shops and great places to eat. Then friends from CT joined, and we enjoyed the kayaks and paddle boards ( supplied) all day of the 4th at Stockbridge Bowl ( lake across the street). Weather was perfect for our 5 min car ride to Tanglewood. And if you are going to Tanglewood from this location, use the "Lions Gate". After the concert we enjoyed fireworks in the parking lot with 20,000 guests, and it only took us less than 5 minutes to get back to the cabin. The only bad thing I can say, is that I didn't want to leave. I'd give this place 6 stars if I could. BOOK IT if available, you will not be disappointed."

Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Perfect for families, groups, or anyone seeking a serene escape, this charming property combines timeless elegance with modern amenities for an unforgettable stay.

Enjoy spacious, beautifully designed rooms that accommodate 8-12 guests, ideal for gatherings or peaceful retreats. Relax in the tranquil garden or explore local landmarks, including the nearby Divine Mercy Shrine, a haven for reflection and spiritual renewal.
Whether you're planning a weekend escape, a family reunion, or a quiet retreat, this one-of-a-kind Stockbridge gem offers comfort, history, and a truly divine experience. Book your stay today and immerse yourself in the beauty of the Berkshires!

- "I stayed here with seven girlfriends, all aged 25-30, for a weekend, and we found it incredibly homey and nice. As a Catholic, it was lovely staying at the rectory, visiting the beautiful altar in the backyard, and knowing that any proceeds from our stay were going to a good cause. All the rooms have saint names, and there is a lot of thoughtful charm throughout. Samantha was very helpful and great at communicating through the entire process. Highly recommend this stay in the heart of Stockbridge, MA."

Located in Stockbridge, enjoy what this 2-bedroom apartment has to offer. This terrific property features 2 queen beds, heating, AC, WiFi, and a washing machine. Our enchanting place will help you feel at home while you're traveling in Stockbridge. This apartment is located on the 3rd floor and requires that you can climb 3 flights of stairs.

- "Very clean and nice apartment. The beds were extremely comfortable. " - "The apartment is in downtown Stockbridge. We were there to aid our son and his fiancee who are traversing the Appalachia Trail. The location was perfect for us. The apartment is complete new and immaculate. It was very comfortable for the four of us. The only reason that the overall review is four not five stars is that the dryer wasn't working and the kitchen had absolutely now supplies or an ice tray. The dryer not working could have been a disaster for us as we needed to clean our son's clothes but fortunately a kindly neighbor helped out. We have reached out to the owner and she was very responsive. We expect that the next people that stay there will not have any issues. We would definitely stay there again."

*This listing is for the 4-bedroom, 4-bath house. The 1-bedroom, 1-bath guest cottage with full kitchen is available for an additional $200/night.*

Room/bed breakdown:

Main House - Downstairs:
Room 1: 1 queen

Main House - Upstairs:
Room 2: 1 king
Room 3: 2 twins
Room 4: 2 twins + 1 twin mattress in loft

Guest Cottage (should you choose to add it on) - Upstairs:
Room 5: 1 queen

Just minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4-bed, 4-bath Colonial home and 1-bed, 1-bath detached guesthouse that sit on a 9+ acre hill with an impressive view of Monument Mountain, a gentle-sloping lawn, abundant woods, and a gentle stream.

A spacious and luxurious retreat for family and friends, the main house offers multiple living spaces with an open kitchen and living room with wood-burning stove, library, billiard room, den/TV room with games and puzzles, and an attached greenhouse with a far infrared sauna that seats 5. An old house lover’s dream, it boasts ultra-wide-plank floors, three fireplaces, wrought iron rim locks, thumb latches, strap hinges, and heavy brass door knobs on hand-planed doors.

The guesthouse with full kitchen is an adorable wooden cottage that feels bright, open, and spacious with its double-high living room. The space was crafted out of a former barn by a local carpenter and has modern amenities alongside its rustic charm. While it is closely-sited to the main home, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. It is the perfect place for hosting extended family and visitors, to be used as a writer’s sanctuary, or for a bridal suite. Everyone who steps inside adores it!

Come experience the best the Berkshires has to offer! Take a walk or a bike ride to the Berkshire Botanical Garden or Naumkeag - or drive a few minutes to downtown Stockbridge, Stockbridge Bowl, Norman Rockwell Museum, Tanglewood, downtown Lenox, West Stockbridge, and Great Barrington.

- "Had a wonderful stay at this old farm! At the end of a secluded, wooded road, this quintessential New England farm house was loaded with charm. If you're looking for something modern, this is not for you. If you're looking for an original, authentic farmhouse you'll love this place. We're New Englanders so this old farm was right up our alley. All the creature comforts. No TV. Great communication and friendly owners." - "The location of this family friendly home was perfect for exploring all of the little towns the Berkshires has to offer. The kitchen was fabulous and well appointed. We loved hanging out in the living room and playing pool in the billiards room. There were so many spots outside for the family to hang out. The 2 year old in our group especially enjoyed the swing and trampoline."

Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 4 bedrooms, dining room, 2 living rooms, 2.5 restrooms, and a screened porch, it offers both cozy comfort and spacious living. Step onto the stone patio and soak in the character of this unique property. Wake up to the soothing sounds of a nearby brook as you savor your morning coffee. Explore over 2 acres of lush land surrounding the house—a perfect setting for daily walks. Tanglewood is just a 5-minute ride away. Positioned between downtown Stockbridge and Lenox, you are close to the renowned Norman Rockwell Museum and Edith Wharton's House, near the serene Stockbridge Botanical Garden. And when the sun sets, the Stockbridge Bowl becomes your favorite summer hangout. Your daily priority list will be mostly about choosing from an array of entertainment and dining options all around you.

Whether you’re drawn to Tanglewood’s melodies or Shakespeare & Co.'s theatrical magic, this beautiful home awaits your arrival!

1. The Berkshire Botanical Garden - a short walk away
2. Norman Rockwell Museum - 2.4 miles away
3. Tanglewood - 3 miles away
4. Naumkeag - 3 miles away
5. Red Lion Inn Lion's Den - 3 miles away
5. Chesterwood - 3.3 miles away
6. Berkshire Theatre Group - 3.3 miles away
7. Kripalu Center for Yoga - 3.3 miles away
8. Turn Park Art - 4.4 miles away
9. The Mount, Edith Wharton's Home - 5 miles away
10. Shakespeare & Co - 5.5 miles away
11. Mahaiwe Performing Arts Center - 10 miles away
12. Jacob's Pillow Dance Company - 16.7 miles away

Pattiserie Lenox - 5 miles
Frankie's in Lenox - 4 miles away
High Lawn Farm - 7 miles away
Bizen Sushi - 10 miles away
Pixie Boulangerie - 9 miles away

- "We loved our time staying here! It accommodated all eight of us easily, and had plenty of parking. The drive to Butternut Ski Resort was very reasonable as well. We will definitely be back!" - "The home is very conveniently located in Stockbridge and all the main sites. It is very spacious, with plenty of seating for a large group. The yard is enormous and scenic, and there is a pathway down to a rapidly moving stream, with chairs and a small table. Wonderful books are available in most of the rooms."

Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soak in the hot tub, shoot some hoops, play some pickleball, or a play game of ball hockey on our private court. Or, explore nearby attractions such as the Norman Rockwell Museum, Tanglewood, and the hiking trails of the Stockbridge area.

-- THE PROPERTY --

MassTaxConnect ID #: C0437672830 | 22-Acre Property | Modern Interior | Gas Fireplace | Private Heated Pool (Depth 3.5’-9’)

Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Den: 2 Twin Futons (converts to King Bed)

OUTDOOR LIVING: Patio, private pool (open seasonally), screened-in porch, hot tub, basketball & pickleball court, gas grill, beach chairs, beach towels, deck, garden, hammock, outdoor shower, outdoor speakers, pool toys, patio heater, gas fire pit
INDOOR LIVING: Board games, piano, Smart TVs, DVD player, books, ceiling fans, walk-in closet, dining table, printer
KITCHEN: Air fryer, drip coffee maker, dishwasher, microwave, knife set, dishware & flatware, ice maker, spices, toaster, cooking basics
GENERAL: Free WiFi, linens & towels, hair dryer, complimentary toiletries, keyless entry, washer & dryer, central heating & air conditioning
FAQ: Steps required, Ring doorbell (facing out), no EV charging
PARKING: Driveway (4 vehicles)

-- THE LOCATION --

OUTDOOR ADVENTURE: Monument Mountain Reservation (6 miles), Berkshire Rivers Fly Fishing (6 miles), Olivia's Overlook (8 miles), Otis Ridge (17 miles)
HITTIN' SLOPES: Butternut Ski Area and Tubing Center (7 miles), Bousquet Mountain Ski Area (12 miles), Catamount Mountain Resort (14 miles), Jiminy Peak Mountain Resort (28 miles)
TIME TRAVEL: Naumkeag (2 miles), Norman Rockwell Museum (3 miles), Ventfort Hall Mansion and Gilded Age Museum (7 miles), Thomas Cole National Historic Site (40 miles), Olana State Historic Site (40 miles)
AIRPORTS: Albany International Airport (51 miles), Bradley International Airport (68 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Guests are not permitted to charge electric vehicles on-site as the electrical system is not equipped for that, and the breaker will blow
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property requires stairs to access
- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed
- NOTE: The pool will be closed from September 29th, 2025, for the remainder of the season and will re-open in the spring

- "Our stay at this Stockbridge home during the July 4th week was perfect. The beautiful, secluded property provided a serene getaway, featuring a well-maintained pool area with a jacuzzi and exquisite gardening. The house is stunning, filled with natural light that makes every room feel warm and inviting. It was the perfect place for two families (with kids) to spend a week enjoying the best the Berkshires have to offer. The location was excellent, giving us easy access to all the local attractions. Plus, the house was well-stocked with plates, dishes, cookware, and everything we needed, which can be hit or miss with house rentals. We look forward to returning!"

The story of this house is so cool! But first ... This *brand new* barn house with vintage furnishings and woods, meadow, and stream sits on 3 acres in a prime Berkshires location - just minutes to Stockbridge, Tanglewood, Lenox. While one can hear the ambient hum of the highway, there is ample privacy with landscaping, wooden fences, and a private deck.

This house is perfect for a couple or for a family.

For a couple, it offers one-level living, with primary bedroom and bathroom, laundry room, den all on the first floor.

For a family, there's ample room upstairs for the kids - two large bedrooms, a full bath, and a hang-out space.

Large windows let in views and lots of light. Radiant concrete floors on first floor are cool in the summer and warm in the winter. Kitchen boasts marble countertops, Rohl faucet, Kohler cast iron sink, Subzero fridge, full-height pantry, long bench for taking in the view. The sitting room opens onto the large cedar deck, perfect for coffee in the morning, drinks at night, or watching the kids play. The den offers plenty of seating, perfect for reading a book or watching a movie on the large screen TV. The primary bedroom is cozy and tucked away, right next to the full bathroom with a 5-foot shower with terrazzo floor and microcement walls.

This all-wood FirstDay Cottage house kit was built in the summer of 2024 by college students and our teenage son with some professional oversight. See the whole process at my blog, Modern Shaker. It is stylish, simple, super-insulated. Come experience how good it feels to live in!

Pet Friendly • Tv • Kitchen • Bedding/Linens • Security/Safety • Balcony/Terrace • Laundry • Sports/Activities • Air Conditioner • Fireplace/Heating • Other • Accessibility

2 Bedroom 2 Bath fully furnished home steps from Main St. This charming house has been totally renovated and has an open, airy feel with a cathedral ceiling in living/dining area. Spacious bedrooms with large closets. $6,000 per month, all inclusive.

Internet • Security/Safety

Keep it simple at this peaceful and centrally-located place. Enter through front door and walk directly into your own room w/ private bathroom/shower & full-size bed. Short walk into quaint town of Stockbridge, access to variety of Berkshire cultural attractions, & 10-minute drive from Kripalu.

Perfect place to get away from hustle and bustle. Nice for a couple's getaway or time on your own. Our family (plus a small, friendly, hypoallergenic dog) may be around, but we'll stay out of your way!

The space
This private room and bathroom are farmhouse simple and free of distractions. In the winter, there is plenty of heat from the radiator and a small space heater is provided if the temperatures drop way down. In the summer there is a window unit AC, plus a fan. In the morning you can make some coffee in the Keurig or visit the excellent Stockbridge Tea & Coffee in town. The mini-fridge is there for restaurant leftovers or if you want to store some pastries from The Lost Lamb. Or maybe you want to just stay in and read a good book in the rocking chair? A microwave is there to heat up any take-out or to-go meals. Towels are provided and there are some bonus items in the cabinets if needed (hair drier, humidifier, extra blankets).

Guest access
You'll have a room and bathroom all to yourself with easy access through the front door of the house. If you need anything, please let us know and we can accommodate you!

Other things to note
If you would like a workspace, please let us know and we can move a small desk into the room for you. There are also two folding TV tables behind the door.

This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While it is a short distance away from our family home and one can hear the ambient hum of the highway, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck.

The cottage sleeps 2 in the queen sleigh bed, but there is seating for a dinner party of 6. It sits on a south-facing hill, looking out towards Monument Mountain. You’ll love it!

The space
This furnished guest house is located on our family compound on 12 acres, just 2 miles from the center of Stockbridge.

Walk into the light-filled, fully-stocked kitchen with Subzero fridge, Viking stove, and island. The dining room table seats 6. There is a full bath with tub and a laundry room off the main living area. The cozy, double-high living room has a soapstone propane stove and 2 stories of windows with view toward Monument Mountain! Upstairs is the queen bed, TV, desk, and reading nook.

Excellent wifi.

*Beyond the north side of the property lies the turnpike, so there is some road noise. We rarely notice it, but we want to point this out to those who are sensitive to traffic noise.*

Guest access
Drive to the top of the road and park to the left. There is a designated path with round pavers that leads to the front door of the cottage. There is an attached side deck for your use. You may also explore the woods and stream on this side of the road, or explore the property (including the hens!) across the road.

Other things to note
There are small children and pets on this property. Please drive slowly up the road and look out for them on either side of the road.

NEW LOWER DAILY RATE: The furnished cottage has a fireplace, vaulted ceilings and skylights which make the space bright, cheery. Perfect for a cozy, romantic quick getaway or a longer stay for an artist's retreat. Just right for 1-2 people- queen size bed, fully equipped kitchen and large bath with tub. The sliding glass doors open onto a deck, overlooking yard and brook. Walking distance to the center of Stockbridge. Internet access is good.NOTE: firewood is not included.

Other things to note
Firewood is not included.
We have a strict non smoking and no pet policy to protect our guests who may have allergies.

Hot water • Iron • Hangers • Bathtub • Room-darkening shades • Hair dryer • Extra pillows and blankets • Cleaning products • Bed linens • Essentials

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

The space
Our studio is a new, modern second floor apartment. Guests will enter through a private side door with keyless entry. Once in the space, kick off your shoes and proceed upstairs to a bright, clean and generous studio apartment with a large kitchenette. The kitchenette has a refrigerator, single hot plate, electric griddle, a large sink, coffee makers and a countertop convection oven, with all the tools needed to make meals throughout your stay. The dining table seats four with plenty of space. A full bathroom will greet you with a large shower and views of the treetops, as well as towels and toiletries. In the main living space, there's a queen-sized bed, as well as a full-sized pullout sofa bed, perfect for a family or a few close friends. There's a spacious closet with plenty of storage space, an iron and ironing board and a hair dryer. When not using the sofa as a bed, it's the center of the living space, alongside a reading nook and a TV, board games, puzzles and a small selection of books.

Other things to note
There is no A/C in this apartment, nor our house. We designed the apartment in a way that utilizes natural ventilation provided by the wind and we use shades to keep it cool during a hot day. We provide directions in the apartment for ways to keep it cool on an unusually hot day.

We live on a main road but we are set well back off the road. The road is much quieter at night but in the day there's a noticable noise if that is something that may bother you.

Shower gel • Garden view • Hair dryer • Hangers • Shampoo • Hot water • Essentials • Cleaning products • Conditioner • Body soap

Keep it simple at this peaceful and centrally-located home. A half mile from down town Stockbridge and a quick drive to great barrington ma! Only 7.5 miles from Butternut Ski (12 minutes) and 12 miles from Bousquet mountain!

The space
Quiet relaxing two bedroom home that includes master bedroom with a king bed and a second bedroom with a queen bed. Semi-open floor plan creating a cozy yet social experience. Large backyard with fire pit, area to play or just relax.
A few minutes to from Butternut ski and Bousquet Ski Mountain! Ski, snowboard, tube or relax by the fire in the Lodge.

Guest access
Off street parking with garage. Half mile from the Red Lion in. A quick drive or a short walk to parks, play grounds, food and drink!

Essentials • Bed linens • Bathtub • Hangers • Conditioner • Cleaning products • Extra pillows and blankets • Hot water • Shampoo • Hair dryer

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

The space
Originally a working dairy farm in the 1940s, the house has been completely renovated. Enjoy a cup of local Six Depot coffee in the window seat, grill on the BBQ and eat dinner outside, or enjoy a movie on the large, Roku TV. The unit is completely private but is connected to our main home.

If you don't feel like cooking but don't want to go out, we also offer home-cooked Indian meals (ordered 24 hours ahead of time). Rukhshida's passion (aside from filmmaking) is cooking and she brought her delicious recipes with her to the Berkshires. Menu and prices can be provided during booking.

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Enjoy our new in-town stylish pied-à-terre , a block from the Red Lion. Off the main thoroughfare just enough but an easy walk for a cocktail on the porch! a stand alone building, large open window filled living/kitchen area, small 2nd floor balcony with chairs to relax, spacious bdrm with king size bed, and a modern tiled bathroom. Central HVAC, great water pressure, all new everything and a well appointed kitchen. July and August are by the week rental only.

Bedroom and laundry • Conditioner • Shampoo • Bathroom • Shower gel • Cleaning products • Washer • Hair dryer • Hot water • Body soap

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting!
That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself.
The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

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Ski Butternut, Catamount, Bousquet & Jimmy Peak, all a short drive. Each an experience . Originally a mercantile building this unique structure is close to everything,. Welcome to Norman Rockwell’s hometown. A Mecca for arts and culture. Tanglewood just minutes away nestled in the heart of the beautiful Berkshires! Naumkeag’s spectacular gardens, gilded mansions & Edith Wharton’s spectacular home await. Historic Red Lion inn a few steps away offering food & music in an original stagecoach stop.

The space
The space is located upstairs above a coffee shop and an art studio. Expect to enjoy the aroma of fresh coffee wafting up as it brews mornings downstairs in the coffee shop. While there is no kitchen the option of a coffee maker, microwave and mini fridge offer the choice of in room make your own or meander downstairs to the coffee shop and explore the options there. Large entryway with bench boot tray and coat hooks immediately as you open the door. Small private full bath with tub is located to the right. Six full towel sets, face cloths, hand towel and bath towels are stored on shelving unit along with 2 bathroom glasses. Full tub unit with shower containing body wash for your bathing pleasure. Sink and mirror with rack underneath containing paper towels and extra bath tissue is located next to toilet. There are towel bars on two walls to Hank towels and a robe hook on the back of the door. Extra towels and linens are stored inside the bench in the entryway. Bedroom has a entrance to a small desk area which also houses the coffee maker, microwave and mini fridge. The door separating the bedroom and office walk-in can be closed for privacy.

Shower gel • Hair dryer • Garden view • Bathtub • Hangers • Cleaning products • Hot water • Essentials • Dryer • Body soap

This special place is close to everything, making it easy to plan your visit.

The space
Beautiful sunny loft apartment with original fireplace! Hardwood floors. Galley kitchen and pretty private bathroom. Cozy sitting area next to Fireplace. Table and chairs for meals with idillic views of Norman Rockwell’s original home and village street while enjoying the cozy fireplace.

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My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic river, and the oldest preserve in Massachusetts - the neighborhood, the ambiance, the comfy beds, the light, the outdoors space. My place is good for couples, solo adventurers, business travelers, and families (with kids). The place is newly renovated.

The space
It's right in the center of Stockbridge. You can walk to all amenities in town, including the Berkshire theaters and the bus that goes to NYC.

Guest access
You can access the entire house, except the basement.

Other things to note
Public tennis courts, basketball courts, Stockbridge Bowl for swimming and boating,
playground( one block away)

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Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

The space
Luxurious linens with brand new Queen beds. Also have 2 single roll away, gel foam beds available. Large bathroom with double vanity, shower with multiple shower heads and deep soak tub. Outdoor space with grill, screened in porch and fenced yard. Fully equipped kitchen with coffee station and walk in pantry.

Other things to note
If you plan to use the indoor fireplace, please bring Duraflame logs with you and only used Duraflame logs. You'll need to make sure that the flu is open when starting the fire and that all embers are extinguished before closing the flu. Flu, if left open, will bleed all heat from the house.

Bathtub • Park view • Shampoo • Mountain view • Hot water • Cleaning products • Shower gel • Body soap • Conditioner • Hair dryer

Spend a weekend in Stockbridge at this idyllic New England home. A perfect Berkshire getaway property, just footsteps from main street Stockbridge, the historic Red Lion Inn, Laurel Hill Trails & Ice Glen hikes. Our local Butternut Basin ski area is just six miles away. A great city escape.

The space
Our house sits just a street from town and on a protected area (and walking trails) called Laurel hill, the oldest land conservation in the country.
In our recent renovation we now have a cooks kitchen, lofted ceilings, fireplace, & stunning BBQ area on the spacious Ipe wood back patio. We also have everything needed for a family with kids. High chair, crib, toys and more!

Guest access
All spaces

Mountain view • Conditioner • Shampoo • Free washer – In unit • Hair dryer • Hot water • Body soap • Cleaning products • Bathtub • Shower gel

Gorgeously restored 1860s Stockbridge home, w/ luxury amenities on 12 acres. Steps to town-enjoy restaurants, shops, museums and culture. A short drive to Lenox and world-renowned Tanglewood music festival, the Stockbridge bowl lake, gorgeous hikes nearby; in winter enjoy skiing and snowshoeing! Just 2.5hrs from NYC and 2hrs from Boston—a perfect getaway. Perfect space for groups with 2 kitchens! For tranquility in the mountains, cultural enrichment, or both, this home offers it all.

The space
This beautifully restored farmhouse is the best of both worlds- formerly a two family, it's large enough for multiple families or groups to share, but has the ability for privacy between the two wings/sides of the building. With two kitchens, multiple bathrooms and bedrooms, a stunning back porch, quiet street but walkable to town, it offers a haven centrally located in the beautiful Berkshires. A quiet weekend for a couple or a family reunion, this is a stunning space for a bustling summer vacation or a cozy winter getaway. 2 living rooms, 2 dining tables, 2 fully stocked kitchens, 2 1/2 bathrooms, washer/dryer, multiple televisions, parking for multiple cars- this home has everything you need.

Guest access
Guests have access to the entire home, back porch, back and side yards. Each reservation will be assigned an individual code for access in and out of the home. Local management available for any questions, or onsite needs.

Other things to note
There is no central A/C in home. We have A/C units for bedrooms during the summer months.
No smoking allowed in or on property
No pets allowed

Shampoo • Dryer • Washer • Bed linens • Bathtub • Hot water • Hangers • Bidet • Cleaning products • Body soap

Amenities include: 3 bedrooms, 2 full baths, main floor primary bedroom (for one level living), high speed cable internet and WIFI, 2 Smart TVs, outdoor fire pit, sun deck with oodles of outdoor seating, all new kitchen appliances, washer/dryer, wood burning fireplace insert, window unit ACs and mini splits to keep you cool, large BBQ grill and more! Please inquire about pets and no smoking, please!

The space
This light and bright home has been beautifully remodeled to be the perfect rental for you to enjoy the Berkshires! Whether you are relaxing on the sunny back deck, or cozying up to the wood burning fireplace after a day of skiing, you’ll love every minute you spend at this fabulous home no matter what time of year you are visiting!

Main Floor: This freshly renovated home has so much to offer its guests! The kitchen is open and bright with all new cabinets and appliances including a fantastic induction cooktop oven, large refrigerator, dishwasher, microwave, toaster, standard drip coffee maker and electric tea kettle. There is a nice sized kitchen island for even more space to prep your meals, as well as a stool for someone to sit on and keep you company while you cook. The dining room table is set up for 6, but can easily accommodate 8 guests, and there is also a separate game table close by that can be used for overflow, as long as you have finished your puzzle or monopoly game. The living room has a large sectional sofa to relax on and a smart TV with Spectrum Cable channels and streaming channels like Netflix, Hulu, and Prime Video available. Or, you can cozy up to the fireplace in one of the comfy chairs to warm up your feet. Just down the hall is the shared full bathroom with a tub/shower combo and the washer and dryer. Continue down the hall to find the primary bedroom with a king size bed, en suite full bath with walk-in shower, dresser and 2 closets for all of your clothes. Just off of the primary bedroom you will discover the office/bonus room with another Smart TV, desk, and plenty of seating. This room is bright and sunny with 3 large windows looking out to the backyard and can be used in a variety of ways, including floor space to spread out on for yoga or meditation, etc. This could also be a fun kid’s space!

Upstairs: On the 2nd floor you will discover the 2 additional bedrooms at the house. One has a queen size bed, a wardrobe and dresser for your clothes. The other bedroom has a full size bed with cubbies to tuck your belongings into.

Outside: Just off the kitchen is the sundeck with oodles of outdoor seating, a large umbrella, fire pit, and large propane BBQ grill. The deck overlooks the backyard and has a lovely view of the wetlands and occasional beaver sightings. The large backyard has plenty of space for outdoor games and a large fire pit perfect for stargazing and roasting marshmallows (or a hot dog on a stick).

Location: Centrally located, this terrific rental is close to all of the Berkshire attractions and venues you want to visit! Just 2 miles to Tanglewood, less than 5 minutes to the Stockbridge Town Beach (on Laurel Lake), 5 minutes to downtown Stockbridge, 15 minutes to Great Barrington, and about 15 minutes to Ski Butternut.

House Rules:
-Guests must be at least 25 years of age to rent the property. Children are always welcome with their parents or guardian.
-All guests are required to sign a lease agreement alongside the airbnb reservation. The lease agreement follows all airbnb rules.
-Pets must be approved and disclosed and a $150 minimum pet fee applies. Pets must be well behaved and not scratch the floors and are advised to not be up on the furniture.
-No Smoking

Guest access
Guests have complete access to the entire home and property.

Other things to note
-Guests must be at least 25 years of age to rent the property. Children are always welcome with their parents or guardian.
-All guests are required to sign a lease agreement alongside the airbnb reservation. The lease agreement follows all airbnb rules.
-Pets must be approved and disclosed and a $150 minimum pet fee applies. Pets must be well behaved and not scratch the floors and are advised to not be up on the furniture.
-No Smoking

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Discover 'Berkshire Retreat': A charming New England home, steps from hiking trails, near ski mountains, and walkable to Stockbridge. Centrally located for Berkshires exploration. Elegant, cozy, and perfectly positioned for your next getaway!

Hot water • Shampoo • Garden view • Park view • Mountain view • Body soap • Washer • Cleaning products • Free dryer – In unit • Bathtub

Walk into town or soak up the sun on the charming 3-season front porch, this renovated historic Stockbridge home is the perfect place to enjoy all the Berkshires have to offer!

The space
Enjoy the whole house and grounds, from your morning coffee on the fully-appointed three-season front porch to cozy evenings watching movies on the large smart t.v. in the living room. Updated kitchen has all appliances to make it feel like home and is stocked with pans, cutlery, glassware, and spices. Three bedrooms upstairs offer the range of king, queen, full, and twin bed-sizes to meet the needs of your family- all with high-end linens on the beds. Stroll our fantastic ‘secret gardens’ with berries, veggies, flowers & fruit which are tended by our local gardener. Savor the unique location of being just steps from the Ice Glen foot bridge leading to gorgeous hiking trails to enjoy the Berkshire fresh air! In the evening, you are also just a footpath away from Main St, Stockbridge where you can stroll through the sites of Rockwell’s most recognizable hometown America as you enjoy shopping and dining.

Guest access
Guests may enjoy the whole house and strolling in our secret gardens & enjoying a cozy fire in the fire pit during chilly evenings!

Other things to note
This is a pet-free and smoke-free property.

Hair dryer • Conditioner • River view • Hot water • Body soap • Garden view • Cleaning products • Shampoo • Bathtub • Shower gel

Hadley House: Amenities include hot tub, wood stove, high speed internet/wifi, 2 tvs, lush gardens, amazing outdoor spaces with seating, festive lights and bbq grill. Outdoor shower with hot and cold water, flower, vegetable, and herb gardens, meditation/reading/sleeping cabin, kayak with direct access to the Konkapot Brook for kayaking or catch and release fishing, chef's kitchen with stainless appliances, washer/dryer, window unit ACs throughout. Pets are considered with fee. No smoking please

The space
Hadley House: a darling Victorian Farmhouse with attention to every detail. This immaculate Stockbridge property sits on 2 acres and has direct access to the Konkapot Brook. Hadley House has a well-organized entry mudroom, with cubbies and bins, for all of your Berkshire gear. The earthen plaster walls and reclaimed barn wood paneling Is warm and inviting. The chef's kitchen has everything you need--with all stainless appliances: dishwasher, 5 burner gas range, large fridge and lots of handy smaller appliances (electric water kettle, coffee maker, citrus press, microwave, toaster, blender, etc.) to make cooking your meals a breeze. The dining room seats 8 and ½ bath are just off the kitchen. The dining room also has a wood stove for those cooler Berkshire nights and so cozy after a soak in the hot tub. The living room has a brand-new sofa with chaise and two leather club chairs, complete with a game cabinet.

Upstairs you have 3 bedrooms – the primary with Queen bed, the guest room, also with Queen and a third bedroom with twin bed. These 3 bedrooms share a brand-new, gorgeous, bathroom with soaking tub and shower. In summer and fall the outdoor shower with both hot and cold water makes a 2nd bath!

The third floor finished attic has a wonderful media room with large HD TV, lots of space for yoga, meditation, and is also a fun kids space with a foosball table. The attic sleep space has a full bed with beautiful mountain views. With AC throughout, the whole house stays cool.

The sunroom leads from kitchen to the outdoor spaces, which are spectacular! Outside, dine alfresco under the trellised patio with table and chairs, outdoor lights and grill. The outdoor shower, with both hot and cold water, is available in the summer and fall and the hot tub is available year-round. The lush garden pathways lead from herb garden, to vegetable, perennials, and a cutting garden. Please, pick and eat! There is also a fabulous meditation/ sleeping shack-a tiny wonderhaus made of reclaimed wood and other creative materials. Its inviting, imaginative, and cozy with its own hammock, fire pit, seating and a tree swing. Surrounding all is the Konkapot River for kayaking and exploring, with catch and release fishing, and nature viewing. The river runs through it… and Hadley House provides a little slice of heaven, for every season.

Close to all Berkshire attraction – less than 15 minutes to Tanglewood, less than 10 to the center of Great Barrington and also less than 15 minutes to Ski Butternut and about 20 to Catamount!

Please see House Rules for more details.

Guest access
Guests will have an easy check in and have complete access to the property. A house manual with important information about the house is provided and guest are encouraged to read it.

Other things to note
Please see the House Rules for all reservation details.

Hangers • Hair dryer • Children’s books and toys • Free washer – In unit • Free dryer – In unit • Bed linens • Essentials • Shampoo • TV • Hot water

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

The space
Villa Favorita was built in 1918, upgraded to its current structure soon after by Clive Livingston Duval I (father of a Virginia Senator of the same name), and later became the home of royalty, Prince and Princess Sapieha, after they escaped Eastern Europe during WWII. Former residents kept their own horses here, and former pasture, equestrian fields and orchards have now evolved into wild meadows, cultivated blackberry and raspberry fields, and pathways through forests of pine, maple and fruit trees.

Five large rooms on the first floor are homey and rich in historic detail. The dining room with large French doors is joined to the modern kitchen through the butler’s pantry. The utility room has a new washer and dryer and a half bath. The living room with built-in bookshelves opens into a spacious front hall with a grand piano and a harpsichord. The first floor also has a comfortable wheelchair-accessible bedroom with handicap shower.

The second floor has five enormous bedrooms overlooking fields and forests; three of these are master bedrooms with en suite baths, and the dimensions of all but one are over 220 square feet.

Guest access
Guests have access to all areas of the house with the exception of the basement, the garage, and the attic above the 3rd floor.

Strolling around our 25 acres you'll find a vegetable and wildflower garden, a fire pit with a park bench and natural stone seating, a small outdoor swimming pool, a chicken coop, meadows (where you can pick blackberries, blueberries and raspberries in season) and pathways through woods and pine groves. As with most of New England we recommend covered shoes and socks to avoid ticks. You'll also notice a house at the far end of the blackberry field (at the beginning of the driveway) and a converted horse barn behind the main house, which are now occupied by 2 of our cohosts. Except for emergencies, please respect their privacy and first contact us by phone if you have any questions or need assistance with anything.

Other things to note
There's a natural glade surrounded by lilacs that's perfect for outdoor gatherings and ceremonies; children love the rope swings under the maple trees off the screen porch; quiet time can be spent in the lovely little greenhouse that's been restored with natural cedar (note, when it's sunny it doubles as a sauna!).

Shower gel • Dryer • Hot water • Washer • Shampoo • Bathtub • Conditioner • Body soap • Essentials • Cleaning products

Nestled in the heart of Stockbridge, Massachusetts, This historic gem has been transformed into an exquisite vacation rental, inviting all Berkshire county travelers to experience a blend of timeless elegance and modern comfort.
Great for small events, groups and wedding parties. Sleeps 8 -12 guests.

The space
The rooms offer comfort and solace while allowing all guests to enjoy privacy. Ample storage, towels and unique amenities suitable for family and group travel. We welcome traveling groups, wedding parties and college groups to book.

Guest access
The entire house is accessible to guests during their stay, except for the attached garage. On Sunday mornings the restroom attached to the laundry room is accessible to church members. Rental restrooms are completely private.

Conditioner • Hair dryer • Free dryer – In unit • Hot water • Free washer – In unit • Shampoo • Cleaning products • Bathtub • Body soap • Mountain view

The house has a large kitchen, dining room and living room with tv and fireplace. The house is surrounded by decks with outdoor furniture.
There are four furnished bedrooms each with a full private full bathroom and a closet. Minimum stay 3 nights. Need to contact the property manager 24 hours in advance to obtain the access code for the front door. Grounds are gorgeous with multiple flower beds. In-ground heated swimming pool in the summer months july and august.. Swim at your own risk.

The space
You will have a fully stocked kitchen, dining room that seats eight, living room with fireplace and 55 inch tv plus use of the decks and outdoor furniture.
The owner has an apartment downstairs on the side with a private entrance. She may be on the grounds on some weekends

Guest access
Kitchen, dining room ( seats eight), living room with tv, decks

Other things to note
By booking this listing you are renting all four bedrooms and bathrooms. To rent one bedroom and share common space with others, please see my listing Brooklyn in the Berkshires 1. To rent two bedrooms and share common space with others please see my listing Brooklyn in the Berkshires. Guests must be 21 years or older. Children of guests are welcome.

Extra pillows and blankets • Essentials • Shampoo • Washer • Hangers • Bed linens • Hot water • Hair dryer • Iron • Dryer

This stylish house is perfect for your next visit to the Berkshires. Cozy, spacious w/ 4 bedrooms, 2.5 restrooms, screened porch, stone patio & lots of character. Enjoy your morning coffee listening to a soothing brook or take a daily walk on 2+ acres of land wrapped around the house. A 5 min ride to Tanglewood, between downtown Stockbridge and Lenox, near Norman Rockwell Museum, the Stockbridge Botanical Garden. All you have to do is select from a long list of entertainment and dining options.

The space
Experience the magic of the Berkshires in this charming two-story retreat, perfectly nestled in the most desirable area of Stockbridge—just minutes from Tanglewood! Whether you're here for world-class music, summer adventures, or a peaceful getaway, our beautifully decorated home offers the perfect setting for unforgettable moments with family and friends.

Step inside to find a warm and inviting space featuring two cozy fireplaces, a piano room, thoughtfully curated bookshelves, and two smart TVs for your entertainment. Designed for art lovers, nature enthusiasts, and those who cherish quality time, this home blends elegance with comfort.

Unwind on the enclosed patio or dine under the stars on the beautiful stone porch. Sip your morning coffee by the private, babbling brook, or find serenity among the majestic trees on over two acres of lush greenery. Whether you're exploring the cultural gems of the Berkshires or simply relaxing in nature, this is your perfect summer escape! 🌿✨

Guest access
Guests have the entire house including the private patio. There is plenty of free parking and it is a breeze to get in and out and to enjoy the most of the Berkshires. The Stockbridge Bowl is minutes away. So is Tanglewood, Edith Wharton's house, Kripalu and everything else the Berkshires have to offer.

Hair dryer • Cleaning products • Courtyard view • Body soap • Garden view • Shampoo • Hot water • Shower gel • Conditioner • Bathtub

Charming Stockbridge Historic Vicotorian Home a Stone Throw Away from the Red Lion Inn. Walk to restaurants, shopping, theatre, tennis, hiking, swiming, skiing. 3,000 sq ft perfect for friends and family gatherings-reunions. Celebrate b-days, weddings , anniversaries, off site meetings. This listing is for the Front House offers LR, DR, Den, Kitchen, 5 Bd, 3.5 Ba, Screened Porch. See separate listing for attached Back House if you need up to another 6 bedrooms and 4 more baths!

Shampoo • Dryer • Hair dryer • Essentials • Extra pillows and blankets • Washer • Hot water • Hangers • Bed linens • Bathtub

*This listing is for the 4-bedroom, 4-bath house. The 1-bedroom, 1-bath guest cottage with full kitchen is available for an additional $200/night.*

Just minutes to Tanglewood! This beautiful home sits on a 10-acre hill with views of Monument Mountain, lawn, woods, and stream. A spacious and luxurious retreat for family and friends, it offers multiple living spaces with an open kitchen, billiards, movies, games, and a sauna. Close to Stockbridge, Lenox, Great Barrington.

The space
Just minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4-bed, 4-bath Colonial home and 1-bed, 1-bath detached cottage that sit on a 9+ acre hill with an impressive view of Monument Mountain, a gentle-sloping lawn, abundant woods, and a gentle stream.

A spacious and luxurious retreat for family and friends, the main house offers multiple living spaces with an open kitchen and living room with wood-burning stove, library, billiard room, den/TV room with games and puzzles, and an attached greenhouse with a far infrared sauna that seats 5. An old house lover’s dream, it boasts ultra-wide-plank floors, three fireplaces, wrought iron rim locks, thumb latches, strap hinges, and heavy brass door knobs on hand-planed doors.

The guesthouse with full kitchen is an adorable wooden cottage that feels bright, open, and spacious with its double-high living room. The space was crafted out of a former barn by a local carpenter and has modern amenities alongside its rustic charm. While it is closely-sited to the main home, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. It is the perfect place for hosting extended family and visitors, to be used as a writer’s sanctuary, or for a bridal suite. Everyone who steps inside adores it!

Come experience the best the Berkshires has to offer! Take a walk or a bike ride to the Berkshire Botanical Garden or Naumkeag - or drive a few minutes to downtown Stockbridge, Stockbridge Bowl, Norman Rockwell Museum, Tanglewood, downtown Lenox, West Stockbridge, and Great Barrington.

Washer • Essentials • Dryer • Bed linens • Air conditioning • Hair dryer • Indoor fireplace • Iron • Pool table • Ethernet connection

Welcome to the Back House at Sergeant St Stockbridge. Brand new handicap accessible 1st floor bedroom with queen bed, en suite roll in shower, shower seat, grab bars and high toilet. Upstairs are 2 king suites each with private baths and 3 bedrooms Queen beds that share a large full bath. Very large eat-in Kitchen seats 8-10, spacious formal dining room seat 8-12 and very spacious living room.
Need 5 more bedrooms and an additional 3.5 baths? See separate listing for the attached Front House.

Hot water • Hangers • Bathtub • Ethernet connection • Hair dryer • Extra pillows and blankets • Essentials • Bed linens • Iron • Shampoo

We've been renting the Taggart House estate for over 10 years. The "guest house" has been our primary home in back of the 3-acre property overlooking the Housatonic River. It's 4500 sq ft w/ 5 bedrooms & 5.5 bathrooms, 25 ft ceilings w/ a beautiful open floor plan w/ lots of sunlight. We are only 2 blocks from downtown Stockbridge & Red Lion Inn; 2 miles from Tanglewood, Norman Rockwell, Chesterwood, & Berkshire Botanical; 6 miles from Butternut & Bosquet; 12 miles from Catamount & Jiminy Peak.

ONLY Labor Day Week 2025 is Currently Available (with 4-Night Minimum Stay)

The estate is located a 3-minute drive from Stockbridge Village and less than 15 minutes to Lenox / Tanglewood, Great Barrington, and Ski Butternut.

This historic home, with sweeping views of the Berkshire mountains & acres of manicured grounds, offers a true getaway. Heated pool is available from June through September.

The space
The first floor has an upgraded kitchen, formal living & dining rooms, library, and family room. A favorite feature is the wraparound glassed-in porch complete with multiple seating areas and dining table. The seating area in the kitchen has a working wood-burning fireplace. A large deck is located off of the kitchen, with an available grill and seating area. There are 4 bedrooms and bathrooms on the second floor. The gracious master suite has excellent views of the Berkshire & Taconic mountain ranges, a soaking tub overlooking the formal gardens, separate shower and dual vanities. A game room on the 3rd floor completes the home.

There is also a TESLA charger located in the garage!

Hot water • Hair dryer • Garden view • Conditioner • Pool view • Bathtub • Body soap • Mountain view • Cleaning products • Shampoo

Welcome to The Taggart House. This stunning estate was constructed in 1850 by noted Stockbridge resident Henry Dwight Sedgwick. For over 150 years, several notables called The Taggart House home, including the psychologist: Erik Erikson. Serving as a Bed & Breakfast for much of the 2000s, The Taggart House was completely restored in 2014 by its current owners. The estate now serves as a vacation rental with The Ballroom used for special occasions only.

The space
The Taggart House is an open, warm home filled with cozy and communal places to celebrate.

Guest access
The entire house is accessible to the guests except The Ballroom, which is only used for an extra fee on special occasions.

Washer • Hair dryer • Bed linens • Extra pillows and blankets • Room-darkening shades • Dryer • Hangers • Hot water • Essentials • Bathtub

Charming 6,000 sq ft Stockbridge Historic Victorian Home a Stone Throw Away from the Red Lion Inn. Walk to restaurants, shopping, theatre, tennis, hiking, swiming and skiing. Perfect for friends and family gatherings-reunions, birthday and anniversary celebrations, bridal and groom festivities, off-site business meetings.

Dryer • Hot water • Hangers • Bathtub • Extra pillows and blankets • Bed linens • Washer • Essentials • Shampoo • Hair dryer

Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situated on 22 acres of pristine land, this vacation rental offers unrivaled privacy and tranquility. Take a dip in the private pool, soak in the hot tub, shoot some hoops, play some pickleball, or a play game of ball hockey on our private court. Or, explore nearby attractions such as the Norman Rockwell Museum, Tanglewood, and the hiking trails of the Stockbridge area.

The space
MassTaxConnect ID #: C0437672830 | 22-Acre Property | Modern Interior | Gas Fireplace | Private Heated Pool (Depth 3.5’-9’)

Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Den: 2 Twin Futons (converts to King Bed)

OUTDOOR LIVING: Patio, screened-in porch, hot tub, basketball & pickleball court, gas grill, beach chairs, beach towels, deck, garden, hammock, outdoor shower, outdoor speakers, pool toys, patio heater, gas fire pit
INDOOR LIVING: Board games, piano, Smart TVs, DVD player, books, ceiling fans, walk-in closet, dining table, printer
KITCHEN: Air fryer, drip coffee maker, dishwasher, microwave, knife set, dishware & flatware, ice maker, spices, toaster, cooking basics
GENERAL: Free WiFi, linens & towels, hair dryer, complimentary toiletries, keyless entry, washer & dryer, central heating & air conditioning
FAQ: Steps required, Ring doorbell (facing out), no EV charging
PARKING: Driveway (4 vehicles)

Guest access
Guests will have access to the entire property via keyless entry

Other things to note
- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Guests are not permitted to charge electric vehicles on-site as the electrical system is not equipped for that, and the breaker will blow
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property requires stairs to access
- NOTE: Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device or when the video doorbell button is pressed

Hair dryer • Bathtub • Bed linens • Shampoo • Outdoor shower • Hangers • Washer • Dryer • Hot water • Essentials