Explore Top Airbnb Vacation Rentals in Stockbridge, MA

Nestled in the heart of central Stockbridge, Massachusetts, this historic hotel offers luxurious accommodations, friendly service and gourmet on-site dining options. We are only a short distance from area points of interest. The Red Lion Inn elegantly combines old-world charm including antiques, tea pots and a birdcage elevator with many modern amenities, including free Wi-Fi. Guests at the hotel can also enjoy the year-round outdoor pool and hot tub and an on-site gift shop. While staying at the Red Lion, guests can enjoy delicious on-site dining options at the hotel's restaurants, The Main Dining Room & Widow Bingham's Tavern both serving classic American cuisine. The Red Lion Inn offers convenient access to a number of area attractions, including the Norman Rockwell Museum. Historic homes, antique shops, boutiques and beautiful gardens are also nearby.

- "Pleasantly nostalgic, and old-style quality" - "We visit very often and have a planned stay that we enjoyed" - "Look forward to going back." - "Wonderful holiday get away in a beautiful little town" - "We would definitely stay there again." - "Completely wonderful!" - "Wonderful stay…" - "Perfect stay . I would love to come again" - "Wonderfully quirky delightful place to stay" - "Loved staying in a historic building and sitting on the porch sipping cold drinks on a hot summer day. The bed were comf"

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."

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.

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

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!"

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.

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

Historic hotel with 3 restaurants and a fitness center
This smoke-free hotel features 3 restaurants, an outdoor pool, and a fitness center. WiFi in public areas is free. Other amenities include a bar/lounge, a 24-hour business center, and coffee/tea in a common area.
The Red Lion Inn offers 125 air-conditioned accommodations with DVD players and bathrobes. Beds feature Frette Italian sheets. Cable television is provided. Bathrooms include shower/tub combinations, complimentary toiletries, and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is offered daily and hypo-allergenic bedding can be requested.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The best Inn! Great town!" - "Comfortable " - "Nice location." - "Historic Inn, we were staying super off peak so price reasonable. Super friendly efficient staff, delicious meal in the tavern. Large comfortable room. Lots of antique eclectic furnishings if you’re looking for cookie cutter mod chain accommodations, this isn’t it. " - "Everyone was so nice and beautiful property " - "Great , relaxed vibe. Had a wonderful weekend. Staff were amazing. Restaurant food just eh. Drinks are pricey but packed a punch. No room service at the Inn. Really missed having coffee in my room in the morning."

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.

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

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.

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

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."

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.

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

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."

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.

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

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."

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.

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

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."

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!

- "We had a very lovely stay at this light-filled cottage close to downtown Stockbridge. Elise & Mickey thought of everything, all the creature comforts, great coffee, fully equipped kitchen, easy to use light switches, Netflix & comfortable temperature. Loved high ceilings, all the light from the big windows, nice private deck. Would stay again. " - "Quiet cabin at the end of a road. Well equipped kitchen, good light, multiple seating areas, comfy bed. Everything was clean and well organized. Highly recommended!"

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."

Spend the SUMMER in the HEART of the BERKSHIRES! JUST minutes from both the Lenox and Stockbridge Town Beach with access to both! 7 minutes from Tanglewood. Experience the MAGIC of Summer in the Berks in this tastefully decorated, fully furnished, and spacious 3 Bedroom & 3 FULL Bath Condo with balcony overlooking the pond. Fully equipped kitchen and smart TV. Just minutes to Stockbridge, Lenox, and Lee! 4 week MINIMUM. Discount available for long term stay! This condo is also available for ski season and the Spring, Set up a time and come for a tour. You will love it!! Check out this video and follow us on insta: @serenelifeberkshires! https://youtube.com/shorts/eHKEvV9MtY8?si=M4XCR6Q3_3Za4EBh

- "This was just the perfect place for me to stay this summer as I planned to be visiting the Tanglewood Music center quite often and it was so close and convenient. It was mostly me for the summer, but I did have a few visitors and the spaciousness of the place made that very easy for us all to be comfortable. and while I was there mostly on my own, I always felt very safe. Jason, the host was just wonderful and even when he was out of the country, he responded to all of my questions so promptly and had so many wonderful suggestions of things to do while I was visiting the area. The deck overlooking Heron Pond was wonderful for having morning coffee or evening, wine, and cheese at the end of a great day in the Berkshires. it was a wonderful summer. At Heron Pond and I highly recommended."

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."

Your Berkshires getaway starts at this sweet 1-bedroom, 1-den condo. The picture windows in the front sitting area look out onto Heron Pond. Sunlight streams in through the skylight in the cathedral ceiling. The bedroom has a comfy queen bed. A second room can be used as a bedroom (with full-sized inflatable mattress), office or yoga studio. Attend Tanglewood concerts, kayak at the Stockbridge bowl, or enjoy music and wine at Balderdash Winery. Tour the Normal Rockwell Museum and Robber-Baron mansions from the gilded age. Feel free to reach out to us during your stay - we're happy to suggest restaurants and other local spots to check out.

Security/Safety • Child Friendly • Fireplace/Heating • Internet • Other • Laundry • Air Conditioner • Bedding/Linens

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