Best Vacation Rentals in West Stockbridge

Top Vacation Rentals in West Stockbridge

Plan your perfect getaway with our selection of vacation rentals in West Stockbridge. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in West Stockbridge
Shaker Mill Inn
Bed & Breakfast
2 Oak Street, West Stockbridge, MA, MA 01266, USA

Shaker Mill Inn enjoys a location in West Stockbridge, 3.9 miles from Tanglewood Musical Center and 4.1 miles from Tanglewood. Both free Wifi and parking on-site are available at the bed and breakfast free of charge. This 5-star bed and breakfast offers private entrance. The bed and breakfast will provide guests with air-conditioned units with an oven, a coffee machine, a shower, bathrobes, a TV with satellite channels, and a DVD player. Each unit comes with a private bathroom and a hair dryer, and certain units at the bed and breakfast have a balcony. At the bed and breakfast, the units are fitted with bed linen and towels. Guests at Shaker Mill Inn can enjoy a continental breakfast, and breakfast in the room is also available. Guests at the accommodation will be able to enjoy activities in and around West Stockbridge, like canoeing and hiking. Skiing, cycling, and fishing are possible within the area, and Shaker Mill Inn offers water sports facilities. Norman Rockwell Museum is 4.3 miles from the bed and breakfast, while Cranwell Spa & Golf Club is 13 miles away. Albany International Airport is 43 miles from the property.

Guest Reviews:

- "The Shaker Mill Inn was a charming, warm, and friendly place to hide out for a weekend." - "Relaxing, clean, comfy, great location in a scenic area, and helpful host couple!" - "A wonderful find off the beaten track." - "Awesome Clean & relaxing." - "Beautiful, inviting & cozy stay in the Berkshires!" - "Excellent experience, would recommend!" - "We would definitely recommend this site!" - "Wonderful overnight in West Stockbridge."

Vacation Rentals in West Stockbridge
Pleasant Valley Motel West Stockbridge
Hotel
42 Stockbridge Rd, West Stockbridge, MA, 01266, USA

Suburban motel in West Stockbridge with free parking
This smoke-free motel features free self parking and free WiFi in public areas.
Pleasant Valley Motel West Stockbridge offers 16 accommodations with hair dryers and irons/ironing boards. Televisions come with cable channels. Refrigerators and microwaves are provided. Bathrooms include shower/tub combinations.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks along with free local calls (restrictions may apply). Housekeeping is provided daily.

Guest Reviews:

- "Loved the location with beautiful views of the surrounding hills. An easy, short drive to the village of West Stockbridge which is an unspoiled jewel that welcomes visitors. The breakfast is nothing special but in the bigger picture, that is a small criticism." - "Easy to get to from I90." - " Great stay for the price " - "We can always depend on a clean room, simple breakfast and most importantly, our clean towels. When there are 3 of us, its gets complicated. The are always available and prompt."

Vacation Rentals in West Stockbridge
Pleasant Valley Motel West Stockbridge
Hotel
42 Stockbridge Road, West Stockbridge, MA, MA 01266

Located in West Stockbridge, 3.4 miles from Norman Rockwell Museum, Pleasant Valley Motel West Stockbridge has accommodations with free WiFi and free private parking. This 2-star motel offers a 24-hour front desk. Cranwell Spa & Golf Club is 12 miles from the motel. At the motel, every room includes a closet. At Pleasant Valley Motel West Stockbridge, rooms come with air conditioning and a flat-screen TV. Tanglewood Musical Center is 6.6 miles from the accommodation, while Tanglewood is 6.8 miles from the property. Albany International Airport is 44 miles away.

Guest Reviews:

- "Most important criteria were met well: clean, quiet, comfortable and in a convenient location." - "Good standard motel, had a nice stay there." - "Good enough for a last resort." - "It was ok but not well take care of" - "Be wary"

Vacation Rentals in West Stockbridge
Shaker Mill Inn
Bed & Breakfast
2 Oak Street, West Stockbridge, MA, 01266, USA

Bed & breakfast in West Stockbridge with free breakfast
Along with a library, this smoke-free bed & breakfast has free breakfast and free self parking. WiFi in public areas is free.
Shaker Mill Inn offers 9 accommodations. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

Guest Reviews:

- "Wonderful property. I would definitely stay there again." - "Great accommodations! " - "Quaint " - "Everything is great!" - "Went away for the weekend to celebrate my daughter’s 30th birthday. This was a perfect spot to relax and not have the feel of a big hotel. " - "Perfect little country inn tucked in the Berkshires, convenient to the highway but off the beaten path on a quiet rural road. Our first floor suite was spacious, inviting, comfortable, and clearly designed with care. Would definitely return next time we’re in the area. "

Vacation Rentals in West Stockbridge
Wellspring by AvantStay Indoor Pool Views
House
Richmond, MA, USA

Wellspring by AvantStay Indoor Pool Views offers accommodations in Richmond, 2.4 miles from Tanglewood Musical Center and 2.6 miles from Tanglewood. This property offers access to a patio and free private parking. The vacation home has an outdoor pool and a sauna. With free Wifi, this vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation offers an air conditioning, a heating, and a private bathroom. Cranwell Spa & Golf Club is 5.4 miles from the vacation home, while Norman Rockwell Museum is 5.6 miles from the property. Albany International Airport is 45 miles away.

Amenities:

Fireplace/Heating • Security/Safety • Wellness Facilities • Accessibility • Child Friendly • Pool • Sports/Activities • Barbecue/Outdoor Cooking • Internet • Air Conditioner • Parking

Vacation Rentals in West Stockbridge
Serene rustic cabin in the Berkshires!
Cabin
West Stockbridge, Massachusetts, USA

Need a break from city life? Escape to our enchanting private cabin nestled in the woods, where romance and seclusion await. This charming retreat offers an intimate setting surrounded by nature, perfect for unwinding. Enjoy cozy evenings by the wood burning stove and serene mornings on the deck, all while being just a few minutes' drive from all the Lenox/Stockbridge attractions, including Tanglewood, museums, cafes, restaurants and hiking/ski trails. Experience the perfect blend of tranquility and convenience in your own woodland haven.

Enjoy quiet mountain serenity, minutes from all Berkshires attractions!

This is a freshly renovated mountain cabin, set on 14 acres of private land at the end of a dead end mountain road. Located on picturesque mountain road in West Stockbridge this home is a short drive from Tanglewood (5 mins), Kripalu (5 mins), Wineries (15 mins), Museums (10 mins), Skiing (20 mins), Hiking (2 mins), Theatre, Shopping and Dining.

This is a perfect location for a romantic getaway or simply a place to come recharge!

The cabin itself sits on 2-3 acres of a larger private estate. There is plenty of lovely green space for walks or pure relaxation in nature.

Guest Reviews:

- "The perfect stress therapy " - "Lovely cabin with a cozy fireplace, snowy views, and easy access to town! " - "Beautiful property and the view of the snow was just perfect, host was accommodating and had the perfect getaway. "

Vacation Rentals in West Stockbridge
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
House
West Stockbridge, Massachusetts, USA

Escape to Tranquility Glade, a newly renovated modern chalet set on 5.5 private forested acres in West Stockbridge, Massachusetts — just 6 minutes drive from Tanglewood and Kripalu. The charming towns of Lenox and Great Barrington are nearby.
Bathed in natural light from skylights and cathedral ceilings, this home combines modern style, curated artwork, and designer furnishings with the calm of a private woodland retreat. The dramatic fieldstone fireplace anchors the open living space, creating a warm, inviting atmosphere year-round.
Enjoy your morning coffee on the spacious deck as sunlight filters through the trees. After a day exploring the Berkshires’ lakes, waterfalls, galleries, and trails, return to relax by the fire or gather under the stars at the outdoor firepit.
Inside, you’ll find a sleek European kitchen, a king bedroom, two queen bedrooms, two full bathrooms, and a spacious lower-level den with a media area, workspace, and fitness equipment. The lower bathroom features a luxurious double walk-in shower — ideal after a hike or day on the slopes.
Every detail is designed for comfort: high-speed WiFi, Air conditioning, a Weber grill, full laundry, toiletries, and all linens provided.
Secluded yet close to everything, Tranquility Glade offers the perfect balance of privacy, design, and location. Whether you’re here for a romantic weekend, a family getaway, or a peaceful work retreat in nature, you’ll arrive as guests and leave restored.
Come stay at Tranquility Glade — your private forest retreat where every morning feels like a fresh start and every evening wraps you in stillness.

Guest Reviews:

- "The property worked out well for the 4 of us to stay in and cook, play games, and read books during the holidays. Great location to explore all that the Berkshires and over the border into NY state has to offer. Local villages with great bookstores, restaurants and taverns, farms, markets, breweries, historic sites, and hiking trails to waterfalls that make for an enjoyable vacation. Michelle was a great host and very communicative. The house was comfortable and had everything we needed to cook great meals, room to relax, and was well decorated, not sparsely appointed and stark like some of the other properties in which we have stayed. I highly recommend this property to anyone looking for a Berkshire retreat."

Vacation Rentals in West Stockbridge
Charming 3-bedroom in-town house in tranquil West Stockbridge
House
West Stockbridge, Massachusetts, USA

This light filled; in-town home is a short walk to the picturesque Village of West Stockbridge. In town you'll find antiques, galleries, gift shops, a rare bookstore, dining, arts and culture, a popular coffee shop, small grocery store, a large outdoor sculpture park and a performing arts venue.
This fantastic location is just five minutes to the main gate of Tanglewood and convenient to all the Berkshires offers: wonderful restaurants, museums and arts festivals, Kripalu and outdoor activities – golf, hiking, ski areas, swimming and boating.
The house features an open concept floor plan. A fully equipped kitchen with a center island opens to a dining room with seating for eight. There is a formal living room and a separate family room with a gas fireplace; both wonderful spaces for reading or watching television. On the first floor is a comfortable bedroom with a queen-sized bed and a nearby full bathroom with a walk-in shower. On the second floor there are two additional bedrooms and a large bathroom with a tub and shower.
The cozy three-season porch and outdoor brick patio have comfortable seating, a fire pit and gas grill offering a place to enjoy nature and gather with friends and family.

Guest Reviews:

- "This was an extremely comfortable home, fully equipped. If you are interested in cooking while you were away, it contains every pot and pan imaginable! The host was extremely accommodating and gracious! We thoroughly enjoyed our stay and the house’s close proximity to the music of Tanglewood. "

Vacation Rentals in West Stockbridge
Location! Location! Berkshire Glamour (and comfort) Meets Town And Country
House
Stockbridge, Massachusetts, USA

One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly renovated designer home was built for entertaining, family vacations, romantic getaway, and/or an outing with friends and musicians. This home was designed with every detail in mind for a comfortable and decadent getaway. Just minutes away (literally minutes) from Tanglewood, Kripalu, Downtown Lenox, Downtown Stockbridge, Norman Rockwell Museum, and many other local attractions. You can't beat the location since its central to all the local attractions.

The interior of this home was designed to please for every member in your family. On approx 2 acres of land with an open backyard and layout, the main floor has a beautiful living room with a Brooklyn fireplace, velvet couch and a 2 person rocking chair, a formal dining room, a beautiful (and magazine featured) kitchen, breakfast nook full of natural light and dining table, cozy and elegant family room, washer/dryer room, and a guest bathroom with a full shower included. Nearly every room has a chandelier that adds to the charm and elegance of this residence.

The 2nd floor, also hard wood floors, includes an art deco guest bathroom with shower and tub, two (2) beautiful guest bedroom with a queen bed, a bedroom with two (2) twin beds designed to be pushed together to make a queen (sheets, comforter, etc all packaged and included), a reading room with a sofa-bed, and an elegant master bedroom with a queen bed, and an enormous bathroom that will make you feel like you're in a spa with a massage tub and two shower-head standing shower. Because we were aiming for this feeling, there are no TVs in the bedrooms on the 2nd floor.

We promise that when you walk into our Berkshire home you'll be impressed with the size, the layout, the natural lighting, the decor, the comfort, and the vicinity to all local Berkshire attractions.

Also, linens, towels, spare toiletries, etc are available in the bathrooms. Wireless internet, satellite tv, netflix, and all utilities are included.

Guest Reviews:

- "We had an amazing stay at this lovely home. It was even bigger than we expected, and every detail was thought of by the owner. All was spotless. This allowed us to have a relaxing stay without having to worry about anything. The home has an incredible location to so much of what we wanted to do in the area. Highly recommended. We absolutely look forward to staying here again!" - "This house was exacly how it was listed. It was such a clean home, very comfortable. The house is very large and gave us lots of privacy. We highly recommended this place and hope to return in the future."

Vacation Rentals in West Stockbridge
Vacation in a Berkshire Farmhouse
Other
West Stockbridge, Massachusetts, USA

Welcome to our idyllic farmhouse in the beautiful Berkshires, where you’ll enjoy the tranquility and comfort of country living any season of the year. Relax, slow down, watch the birds in the garden, listen to the babbling brook. Or take advantage of all the Berkshires has to offer – cultural attractions, fine dining, outdoor adventures, shopping and more. Spend some time here and create memories for years to come.
This is a 2 story 1840's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house.
Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains.

It has a fully equipped country kitchen with dish washer, microwave, toaster oven, coffee maker, and lots of cooking utensils.

A full dining room with butcher block table that seats 12 and 2 complete sets of dinnerware; glasses, mugs, and wine glasses.

A large living room with 2 full couches (one is a comfortable queen pull out and the other is a great napping or over night sleeping couch), a love seat, and rocking chairs. WiFi/Cable TV/VCR/DVD/Stereo/and CD player.

1 bedrooms upstairs with queen bed, 2 with double beds, and 1 with single bed.

1 bedroom downstairs with king bed.

All beds have memory foam toppers, all linens included.
1 COMFORTABLE (really) queen pull out couch in living room

Downstairs bathroom has washer and dryer with soap; shower has soap and towels.

Perennial gardens and large vegetable garden.

2 miles from downtown West Stockbridge where you can shop and dine; 2 minutes from Card Lake Pond for swimming and fishing; 15-20 minutes to ski areas; 10 minutes from Tanglewood, theatres and movies; 10 minutes from Norman Rockwell Museum; 20 minutes to Pittsfield; 2.25 hours from Boston; 2.5 hours from NYC.

Wooded and river walks/bicycling, cross country skiing/snowshoeing right out the door.

Guest Reviews:

- "Comfortable home, good setting, close to Tanglewood, and a friendly, accommodating host ((Elaine Hoffman). There was a lovely sunporch, a grill, and outside space for games!" - "The property was beautiful and well maintained. The owner, Elaine, has put a lot of thought and care into the place. We had a great stay. I hope we make it back sometime soon." - "This is a quaint farmhouse with a fabulous porch for breakfast and evening cocktails. The beds were comfortable, plenty of hot water and the hostess, Elaine has thought of everything you could possibly need. She shares her fresh produce from her garden to add to our meals. She is very helpful with directions and information on local sites. The location is perfect for exploring the best the Bershires has to offer! We had a wonderful week! We look forward to returning soon!"

Vacation Rentals in West Stockbridge
4 BR home w/beautiful gardens on pond in Berkshires. Walking distance to town.
House
West Stockbridge, Massachusetts, USA

This house is close to Everything!! Tanglewood (3 miles), Kripalu (3 miles), theaters, Jacob's Pillow, Lee Outlets, etc.

This house has a NEW and very large MBR on the first floor with adjacent bathroom.. It also has 3 bedrooms and a bathroom upstairs. Sleeps 11. Highlights: Central air, private English garden and gazebo, updated eat-in kitchen, mud room, bar area, and new 1st floor bathroom. House is located on Shaker Mill Pond with dock access. Perfect for a family vacation getaway with lots of space for people to come together or to have their own space. Large sunroom off kitchen has great views of the water. Large multi tiered deck off sunroom is great for relaxing and entertaining. In addition, there is a separate living room with lots of space.

There is a dock on the water for easy access for kayaking and canoeing. Not a swimming pond.

It is the type of house where you walk inside and instantly relax.

Guest Reviews:

- "We loved the house, the location, and the property. Great place to relax and enjoy the town and the area." - "Chris is a great host. He was responsive to any questions we had. There was so much to do in the area that we were out for most of the day. It was great to come back to the peaceful property. We loved sitting out back. We started every morning with a quick walk down to Sixth Depot for coffee. Do not miss Turn Park sculpture garden which is just steps away. High Lawn Farms ice cream was a fan favorite. Great week!"

Vacation Rentals in West Stockbridge
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
House
Stockbridge, Massachusetts, USA

Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while just minutes away from many local attractions!

We are excited to be hosting short term guests again as we've had long term tenants for the last 2 years. We recently refinished the hardwood floors, replaced the stove, installed a new kitchen floor and repainted the interior.

The main floor includes a fully stocked kitchen, living room, full bath, bedroom (king) and another bedroom (twin) / office.

The upper level includes the master bedroom (queen), another bedroom (2 twins) and a full bath.

The basement has another TV lounge area and is where the washer/dryer are located.

There is a huge deck that spans the length of the house with outdoor furniture & a BBQ for your enjoyment.

Guests have use of the entire house. There is an apartment above the garage where our long term tenants reside (nice couple). There are separate entrances to ensure privacy for both parties.

Linens, towels, soap, shampoo and spare toiletries are available in the bathrooms. High speed / wireless internet, cable tv and all utilities are included.

Guest Reviews:

- "We had a great stay. It started with the owner who is super responsive, easy to deal with and helpful. The house itself is cozy and comfortable. Appreciated all the basics supplies (extra sheets towels, laundry detergent, oils, spices, napkins paper towels) in the house and how centrally located the house is (10-15 mins from Lenox, Great Barrington and Lee). My only complaints (and this is me being picky) is that the room with twin beds (kids room) had sheer curtains, so it was hard for them to sleep in and there weren't a ton of serving dishes and bowls in the kitchen, BUT I would certainly recommend this house to anyone!"

Vacation Rentals in West Stockbridge
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Condo
West Stockbridge, Massachusetts, USA

Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the culture.

Minutes away from Tanglewood Music Center, Kripalu and near Lenox, Great Barrington, the Norman Rockwell Museum, and Jacob's Pillow.

Less than 5 minutes away from Stockbridge Bowl / Lake Mahkeenac's boat launch ramp for all you fishers and kayakers out there!

**If the weekend you want is unavailable, please email us to see if our other unit is available!**

Mattresses were replaced in June 2021

Guest Reviews:

- "We are a family of 5 plus 2 dogs spending two nights in the Berkshires to get some skiing in. Carmen’s property was perfect for us - cozy, warm, comfortable. Easy access to our favorite restaurants in Lenox as well as Ski Butternut. We will return! The O’Grady Family" - "The condo is close to many nice towns to visit, the beautiful Stockbridge bowl and in a very quiet area. The condo itself is very clean and spacious, just right for two people but could work for a few more."

Vacation Rentals in West Stockbridge
Perfect setting for Family Vacations Short and Long Term Stays Welcomed.
House
West Stockbridge, Massachusetts, USA

Private Estate Centrally located to all Berkshire attractions and just mins. from the Mass Pike.
Perfect for any event. Wedding, Reunions, Business get aways.
Large chefs kitchen with 60" Wolf Range, Subzero Refrigerator/Freezer, and massive island with white marble thru out.
A screened porch off the kitchen with BBQ grill right outside makes enjoying the Berkshire weather a perfect place to have meals or an afternoon snack. Easy access to Tanglewood, Stockbridge, Great Barrington, Lenox. Great restaurants are a few minutes drive along with shopping and Museums. All attractions and summer theater are very close by.
4 Bedrooms, a Den with Queen pullout couch and bath
Bedroom Descriptions
(2) Masters both with King Beds 1 on first floor the other on 2nd floor both with full baths 1 room Queen Bed other King share full bath on 2nd floor
Den with pull out queen sleeper with bath
Lower level includes gym, pool table, Large screen TV, 2 very comfortable couches for extra sleeping and a full bath

Guest Reviews:

- "The property and owners were wonderful and considerate. They were very communicative and the house was perfect for my family’s stay. Beautiful home and thank you for sharing it with us!" - "The spaciousness and fine appointments of the property were a wonderful surprise. The house was a huge hit with the whole family. The kitchen was well stocked with all supplies. Amenities and extras included a fire pit and a zip line." - "My family very much enjoyed our long weekend at Amy and David's beautiful house. We were in the Berkshires for my niece's wedding, and the house provided all of the comforts we could possibly need. We especially enjoyed the spacious screened porch, the super large kitchen, and the luxurious bedrooms and bathrooms. We appreciated that Amy and David were around if we needed them, but other than welcoming us and giving us a tour of the house, gave us privacy and space to enjoy their home and surrounding land. We will definitely reach out to the Pearlsons next time we need a large house in the Berkshires."

Vacation Rentals in West Stockbridge
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Condo
West Stockbridge, Massachusetts, USA

Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This 2BR home can sleep up to 6 people. All of our mattresses have been replaced in June '21.

Enjoy a nice cup of hot chocolate by the fireplace in the living room after a day of exploring the town.

★ LOCATION ★
We're conveniently located in the middle of these major attractions:

• Kripalu Center For Yoga & Health (4 minutes away)
• Tanglewood (5 minutes away)
• Stockbridge Bowl - has a cute beach and boat launch ramp (3 minutes drive, 10 minutes walk)
• Norman Rockwell Museum (7 minutes away)
• Butternut - great for skiing (20 minutes away)
• Jacob's Pillow (30 minutes away)

★ GUESTS ★
Our cute and convenient condo is perfect for:
• couples on a romantic getaway
• families on a ski trip
• friends on a long overdue trip to reconnect
• performing artists from Tanglewood
• those looking for longterm or temporary housing
All are welcome!

★ ABOUT ★

CONDO
• Ground floor (no stairs)
• 1 Floor
• 2 Bedroom
• 1 Bathroom
• Large yard
• Parking

LIVING ROOM
• Gas fireplace
• Sofa bed
• TV

KITCHEN
• Dishwasher
• Washer and dryer (perfect after a day of hiking or skiing!)
• Utensils, plates, pots, pans, etc. - everything you need to have a nice home cooked meal

DINING ROOM
• Dining table - seats 4

BEDROOM
• Queen bed
• Side table

BATHROOM
• Hair dryer

OUTDOORS
• Guests are welcome to bring their own BBQ grill and outdoor seating to be enjoyed in the large outdoor space

★ PETS POLICY ★
Pets allowed (weight and breed restrictions may apply). There is a $150 non-refundable pet fee.

★ COVID-19 SANITIZATION ★
Heath, safety, and wellbeing of our guests are of the utmost importance. For this reason, we use a thorough cleaning process after each check-out.

If the weekend you want is unavailable, email us to see if our unit next door is!

Guest Reviews:

- "This condo worked out well for my sister and myself for our time checking out Lenox, Stockbridge and our trip to Tanglewood. The location is only a few minutes away from Tanglewood. Carmen always responded right away to email whenever I had a question. The bedrooms were a good size and the kitchen had everything we needed for a short stay. The beds were very comfortable." - "Perfect, cozy spot. Thank you" - "The was an ideal location for our fall getaway. It allowed us to travel and see many of the small Berkshire towns and sights. Definitely recommend this place to stay."

Vacation Rentals in West Stockbridge
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
House
West Stockbridge, Massachusetts, USA

A Writer’s Haven!!!

360-degree scenic PRIVACY. YET… just 1/2 mile off the Mass Pike and 15 minutes from Tanglewood, Lenox & Stockbridge! DOG FRIENDLY! Large fenced-in dog pen.

As you enter the long, private, tree-lined drive, you'll find yourself enveloped in magically scenic, peaceful and lush surroundings.

Once inside, the amazing original wood-beam ceiling and massive picture windows with gorgeous views will captivate you. The house is updated enough with all necessary comforts, but we've preserved the country charm of this farmhouse (built in 1875) in every way possible. Examples include exposed post & beam corners, salvaged hardwood floors, the oversized clawfoot bathtub and a 16-gauge copper farmhouse sink in the kitchen. The property is a peaceful, private, serene and magical place that you'll have all to yourself, yet you'll be just 10-15 minutes from the best attractions in the area and less than 1 minute from the Mass Pike!

CALLING ALL TRAINSPOTTERS AND RAILFANS! One of the unique features of the property is its proximity to a railroad track that is used by both Amtrak as well as cargo trains. The track is adjacent to the southern border of the property, and this affords you a very cool view of the various types of trains that go by.

Most find the trains' sounds a unique, cool part of the experience here. And many find the passing train sounds soothing. Most say that after a couple of days they no longer notice trains passing by.

Sometimes there are only 1 or 2 trains in a 24 hour period. Sometimes there are as many as 15 in a 24 hour period.

The trains do honk their horns as they're approaching, because the house is near a RR crossing. Some find the horn to be loud.

For those who prefer not to hear them at night (they do occasionally run in the evening), ear plugs are provided for each guest. However, most say that after a day or two here, they don't notice the train horn much.

The house has high speed internet / wifi and a television with Roku (you'll log into your own Hulu, Netflix, Amazon, etc. accounts). There are portable air conditioner units in the two larger bedrooms (primarily for sleeping...not 24/7 use). And a cooling fan is available for the smaller guest bedroom.

A Culligan water softener / filtration system services the entire house, the source of which is fresh well water.

FULL STANDBY POWER GENERATOR! Should a storm cause the house to lose power, the 14Kw stand-by power generator will kick on automatically, providing enough power for the important things (water, heat, fridge, lights in most spaces, microwave ((but not the stove/range)), wi-fi, tv, etc.) When power resumes, the generator will switch back to the regular power source automatically.

This property is very, very special. And it's very private, yet super close to Tanglewood, Kripalu, Stockbridge, Lenox, etc.

You can have a baseball game out on the lawn, go Forest Bathing in our 5 acres of untouched woods, catch glimpses of the diverse wildlife on and around the property, and you can park numerous vehicles on the driveway -- you'll have so much scenic acreage to use as you please. It's like an enchanting retreat, yet it's very close to most of the cultural and recreational attractions that make the Berkshires so very special. ONE DOG PER STAY IS WELCOME: Large fenced-in dog pen! (kindly have nails trimmed before arrival)

*Note: furnishings / décor are subject to change

Guest Reviews:

- "Well maintained, has everything you need, and it's in a great location. The hosts communicated regularly and getting in was a breeze." - "The house is very comfortable and the location is beautiful and convenient for walks, hikes, shopping, dining, etc. Lisa, the owner, is lovely and responsive - we were greeted with a personalized welcome note and bottle of wine.an overall great experience." - "This house is on a very large property with no neighbors in sight. The lily pond outside the kitchen deck offers lots of wildlife viewing. The windows are practically sound-proof and the climate control by room is very effective. There are cute Knick knacks about and a bunch of engaging books. We had a very relaxing escape without feeling too far from Great Barrington, Lenox or Stockbridge."

Vacation Rentals in West Stockbridge
West Stockbridge Sanctuary by Evergreen Home
House
West Stockbridge, Massachusetts, USA

12 MINUTES TO BOUSQUET MOUNTAIN
Enjoy a getaway to the Berkshires in this magnificent post & beam home; newly renovated and nestled on 1 acre of land - just 3 minutes from downtown West Stockbridge, and 8 minutes to Tanglewood.

Located in picturesque West Stockbridge, MA this home is a short drive from all the Berkshires has to offer. Enjoy quiet country living, minutes from all Berkshires attractions. Pack your hiking shoes and explore the Berkshires in the spring from this central location!

If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.

This is a quiet neighborhood road. The home is set back from the street.

Guests will have access to the entire home, and property.

This 1,821 sq foot home features an open concept main floor with a light filled living room containing a smart TV and sectional for the perfect Berkshire nights. The full kitchen includes all new stainless steel appliances. The dining room is located right off of the kitchen with additional seating available in the sunporch for six guests.

The first bedroom, containing a queen bed, is located on the main level of the house. The first floor also has a full bathroom with a tub/shower combo.

The additional two bedrooms and second full bath are located on the second floor. Bedroom #2 has a king bed and bedroom #3 has a full bed as well as two twin beds available. A desk and chair located in the second bedroom make for the perfect private work space.

Enjoy cozy nights outside seated on the outdoor furniture around the propane fire pit. A BBQ and outdoor dining area is also located in the private backyard.

Drive to Butternut Mountain, Bosquet or Catamount Mountain in under 30 minutes. Venture out for cross country skiing, ice skating, ice fishing & more FUN winter activities or catch a show or visit a museum. Drive to Tanglewood, The Colonial Theatre, Barrington Stage Co, Berkshire Museum, shopping & wonderful restaurants in under 20 minutes!

Your perfect, private oasis while enjoying all the Berkshires has to offer!

You can walk in the neighborhood, but will need a car to get around the Berkshires effectively.

LOCATION: This is a quiet neighborhood road. The home is set back from the street.
PETS: A small, trained, hypoallergenic dog is allowed on a case by case basis and for an additional $100 fee. Any pets must be under 50 lbs and fully housebroken/trained. If you'd like you to bring your pet, please let us know so we can ensure they are safe at our unique property. No multiples.
PARKING: Free parking on premises.
*Please refrain from outside noise after 10pm since this home is situated in a neighborhood.
*Pink flags are on the property to mark the property line, please do not cross this line into the neighbors property.

**Your reservation includes a $20 insurance fee to cover any accidental damage during your stay, allowing you to relax and enjoy your vacation with peace of mind. If any damage does occur, please let us know so we can arrange timely replacements for the next guest.

Guest Reviews:

- "Charming, comfortable home on a beautiful property. Perfect location—close proximity to everything the Berkshires has to offer. Our family of 5 (plus granddog) thoroughly enjoyed our five-night stay." - "The West Stockbridge house was clean and attractive. It was in a quiet location a short drive from town. West Stockbridge has some charming features for a small town - a good coffee place (Depot #6), a good bookstore, a classic hardware store, and the best place to go for vanilla. The nearby towns have good restaurants."

Vacation Rentals in West Stockbridge
Indoor Pool & Lofted Game Area | Sunroom w/Sweeping Mountain Views | Wellspring
House
West Stockbridge, Massachusetts, USA

Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. This gorgeous home has been newly renovated with carefully curated details for a sense of elevated comfort. The crown jewel of this home is its indoor pool — a haven where you can enjoy a dip no matter the season. There is a poolside lounge area and an airy sunroom where you can enjoy a breeze space with tons of natural light.

Perfect for groups, Wellspring offers a variety of indoor areas where everyone can spread out and relax. There are two living rooms, as well as a lofted game area. Between the large dining table and breakfast nook, there's seating enough for everyone. The renovated kitchen boasts refreshed countertops, cabinetry, and a backsplash, and is fully equipped with new cooking essentials and serveware for at-home meals. And with convenient grocery shopping less than 10 minutes away, it's easy to keep the kitchen stocked.

Spend your evenings on the spacious patio as you fire up the grill, dine al fresco at the outdoor table, and enjoy the surrounding views. Inside, a wide selection of sleeping arrangements ensures everyone has a comfortable space to call their own.

You'll be on a large private lot, giving you the ultimate sense of seclusion. Contemporary design, one-of-a-kind spaces, and top-notch amenities combine to show your group a Berkshire experience they won't soon forget.

AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team and a tech-enabled concierge to book services, such as fridge stocking, mid-stay cleanings, and private chefs. For anything you need (or never knew you needed), we're at your service!

A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself!

Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort.

Home Truths:
- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.
- Pool heat is available for an additional fee but must be requested before your stay.
- The fireplace in the primary bedroom is not for guest use.
- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.
- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.
- Parties, events, and weddings are strictly prohibited at this property. Any violation may result in fines and immediate eviction without refund.

Parking Details:
- The driveway accommodates 6 cars.
- The garage accommodates 1 car.

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The room configuration is as follows:

Primary Bedroom / King bed
Bedroom 2 / Queen bed
Bedroom 3 / Twin bed
Bedroom 4 / Queen bed
Bedroom 5 / 4 twin beds
Bedroom 6 / Twin bed
Bedroom 7 / 2 double beds
+ 2 twin size tri-fold sleeping mats

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Accidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.

This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 30 days require a security deposit.

We report and prosecute all Credit Card Fraud.

Guest Reviews:

- "The one problem we had with this property was the fact that only 2 of the 5 TV's were not working. I would suggest you have all of the TV's in working order." - "We had the whole family come together to stay for the weekend and celebrated two birthdays while relaxing at the peaceful property. The pool was the main focus of our stay!!" - "We stayed for a girls weekend away. There was plenty of space for everyone to be comfortable and had a great time. The location was great - close to Downtown Lenox, Tanglewood and Miraval. While there is AC in the house, there is a portion that does not; it was cool enough at night with the windows open that for us it wasn't an issue. Lastly, bedroom 6 is in a common area without a door; again, not an issue for our group just something to note. Would definitely recommend staying here!"

Vacation Rentals in West Stockbridge
Large Mountaintop Retreat in the Berkshires
House
West Stockbridge, Massachusetts, USA

This secluded Mountaintop Retreat is in the very heart of the Berkshires.
The 8 acre property is a 3 minute drive to the village of West Stockbridge.
The ski area of Jiminy Peak is 25 minutes away and Tanglewood 10.
The 4200 square foot house is set back from the road at the end of a 1/4 mile private driveway that winds uphill through a bird sanctuary. The house has a wonderful view of the Berkshire mountains.

The space
This spacious and bright house has 4,200 sq ft of living space spread out over two floors. The ground floor has a large living room with an open fireplace, a formal dining area, a brand new kitchen, a breakfast nook, a master bedroom suite, as well as a powder room.

The second floor has two spacious bedrooms, one with an open fireplace, a large tv screen, and a private bathroom, the other with an adjoining private bathroom. Both have a sink, bath and shower. All rooms enjoy large closets as well as ample linens. Between the bedrooms there is a high and open hallway with a cozy landing where guests can sit and enjoy the view of the mountains.

The basement contains a large den with a wall lined with a large variety of books. Next to it there is a laundry room with a washer and dryer.
At the front of the house there is a wooden deck, and at the back a screened patio. Both offer ample room to enjoy your meals with plenty of seating and a barbecue.

Eclectic antique furnishings throughout the house make this a unique place to spend your holidays.
Guest access
The entire 4200 foot house as well as the 8 acres of land that surround it, is dedicated to the enjoyment of its guests.

Guest Reviews:

- "Enjoyed renting this property, very private location and plenty of space. Lovely touches such as free firewood and wine for guests. Wonderful place to stay near Stockbridge." - "We very much enjoyed our stay! We admired the charming and unique furnishings, and we thought they made the house more interesting and memorable. The home itself is very large and allowed the 5 of us to spread out and have quiet time on our own. Wifi worked great. I believe the owner is working on making improvements re: issues raised in the other guests' reviews, which were minor to us. The location is quiet/secluded and very convenient for visiting the attractions in Stockbridge/Lenox/Great Barrington, and Tanglewood. We hope to come back to stay again."

Vacation Rentals in West Stockbridge
Modern Cabin Near Tanglewood
Cabin
West Stockbridge, Massachusetts, USA

Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.

This log cabin is surrounded by tall towering trees with a quaint exterior and a surprisingly spacious open interior. Its design is updated while keeping the integrity of the cabin appeal. All bedrooms and living room have split systems with A/C and heat!
The main floor includes a living room, dining room, well stocked kitchen , bathroom with shower and one king bedroom.
The basement is a great kids and adult space where you can cozy up and watch movies, shoot some hoops with the arcade game "hot shot" and the kids still have an extra bedroom to play in, equipped with games and activities.
The upstairs has an spacious king master with work space, a full bathroom with tub and another guest king bedroom.
The exterior includes a space to have a fire and play outdoor games with plenty of seating and a hammock to lounge

Guest Reviews:

- "Our stay was fabulous!" - "This is a lovely cabin with a fire pit, surrounded by trees and yet close enough to walk into West Stockbridge. Hosts were prompt to reply to our messages and very helpful. One of the nicer properties we have stayed in!" - "We had an amazing 5 nights in the cabin! It was extremely clean, had everything we needed to cook for a few nights, centrally located to many features of the Berkshires, and a has cozy porch and yard to hang out. We used it as a home base but also to relax, watch movies, watch the sunset and enjoy a campfire. Thank you for sharing this lovely property with us!"

West Stockbridge Vacation rentals with Parking

West Stockbridge Family Friendly Vacation rentals

West Stockbridge Vacation rentals with Entertainment

West Stockbridge Pet Friendly Vacation rentals

West Stockbridge Vacation rentals with Private Pool

West Stockbridge Vacation rentals with Spa

West Stockbridge Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in West Stockbridge – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Shaker Mill Inn 2 Oak Street, West Stockbridge, MA, MA 01266, USA 260 5.0 9.2 88 Click here
Pleasant Valley Motel West Stockbridge 42 Stockbridge Rd, West Stockbridge, MA, 01266, USA 66 2.0 6.8 1001 Click here
Pleasant Valley Motel West Stockbridge 42 Stockbridge Road, West Stockbridge, MA, MA 01266 79 2.0 5.4 116 Click here
Shaker Mill Inn 2 Oak Street, West Stockbridge, MA, 01266, USA 117 2.0 9.6 435 Click here
Wellspring by AvantStay Indoor Pool Views Richmond, MA, USA 960 1 Click here
Serene rustic cabin in the Berkshires! West Stockbridge, Massachusetts, USA 248 2.0 10.0 5 Click here
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood West Stockbridge, Massachusetts, USA 393 2.0 10.0 4 Click here
Charming 3-bedroom in-town house in tranquil West Stockbridge West Stockbridge, Massachusetts, USA 388 2.0 10.0 2 Click here
Location! Location! Berkshire Glamour (and comfort) Meets Town And Country Stockbridge, Massachusetts, USA 442 10.0 133 Click here
Vacation in a Berkshire Farmhouse West Stockbridge, Massachusetts, USA 373 9.8 97 Click here
4 BR home w/beautiful gardens on pond in Berkshires. Walking distance to town. West Stockbridge, Massachusetts, USA 116 10.0 75 Click here
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires! Stockbridge, Massachusetts, USA 285 10.0 70 Click here
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood) West Stockbridge, Massachusetts, USA 280 9.2 61 Click here
Perfect setting for Family Vacations Short and Long Term Stays Welcomed. West Stockbridge, Massachusetts, USA 1087 10.0 50 Click here
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) West Stockbridge, Massachusetts, USA 212 9.2 36 Click here
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood West Stockbridge, Massachusetts, USA 288 9.8 22 Click here
West Stockbridge Sanctuary by Evergreen Home West Stockbridge, Massachusetts, USA 496 9.8 16 Click here
Indoor Pool & Lofted Game Area | Sunroom w/Sweeping Mountain Views | Wellspring West Stockbridge, Massachusetts, USA 1254 10.0 14 Click here
Large Mountaintop Retreat in the Berkshires West Stockbridge, Massachusetts, USA 534 8.6 12 Click here
Modern Cabin Near Tanglewood West Stockbridge, Massachusetts, USA 584 10.0 10 Click here

Note: The prices for each Vacation-Rentals in West Stockbridge do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in West Stockbridge that include a pool include:

  • Wellspring by AvantStay Indoor Pool Views.- Review Count: 0, Rating: 0.0
  • Vacation in a Berkshire Farmhouse.- Review Count: 97, Rating: 9.8
  • Indoor Pool & Lofted Game Area | Sunroom w/Sweeping Mountain Views | Wellspring.- Review Count: 14, Rating: 10.0

These vacation rentals in West Stockbridge provide spa or wellness access:

  • Indoor Pool & Lofted Game Area | Sunroom w/Sweeping Mountain Views | Wellspring.- Review Count: 14, Rating: 10.0
  • Expansive Rustic and Modern Berkshires Estate on 66 Acres, Mountain Views,..- Review Count: 3, Rating: 10.0

Family-friendly vacation rentals in West Stockbridge include:

  • Shaker Mill Inn.- Review Count: 88, Rating: 9.2
  • Pleasant Valley Motel West Stockbridge.- Review Count: 1001, Rating: 6.8
  • Pleasant Valley Motel West Stockbridge.- Review Count: 116, Rating: 5.4

Pet-friendly vacation rentals in West Stockbridge include:

  • Shaker Mill Inn.- Review Count: 88, Rating: 9.2
  • Location! Location! Berkshire Glamour (and comfort) Meets Town And Country.- Review Count: 133, Rating: 10.0
  • Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood).- Review Count: 61, Rating: 9.2

Vacation rentals in West Stockbridge that include breakfast options include:

  • Shaker Mill Inn.- Review Count: 88, Rating: 9.2
  • Shaker Mill Inn.- Review Count: 435, Rating: 9.6

Vacation rentals in West Stockbridge with private or on-site parking include:

  • Shaker Mill Inn.- Review Count: 88, Rating: 9.2
  • Pleasant Valley Motel West Stockbridge.- Review Count: 1001, Rating: 6.8
  • Pleasant Valley Motel West Stockbridge.- Review Count: 116, Rating: 5.4

Some of the best Vacation Rentals in West Stockbridge are:

  • Shaker Mill Inn.- Review Count: 88, Rating: 9.2
  • Pleasant Valley Motel West Stockbridge.- Review Count: 1001, Rating: 6.8
  • Shaker Mill Inn.- Review Count: 435, Rating: 9.6

Some of the popular Vacation Rentals in West Stockbridge are:

  • Pleasant Valley Motel West Stockbridge.- Review Count: 1001, Rating: 6.8
  • Shaker Mill Inn.- Review Count: 435, Rating: 9.6
  • Location! Location! Berkshire Glamour (and comfort) Meets Town And Country.- Review Count: 133, Rating: 10.0