Places to stay in West Stockbridge

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for West Stockbridge places to stay

Stay near West Stockbridge's top sights

Norman Rockwell Museum344 locals recommend
Berkshire Botanical Garden118 locals recommend
No. Six Depot Roastery & Cafe82 locals recommend
Berkshire Mountain Bakery Inc64 locals recommend
Chesterwood63 locals recommend
Olivia's Overlook51 locals recommend

Other great vacation rentals in West Stockbridge

Top guest favorite
An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.
Home in Millerton
4.97 out of 5 average rating, 181 reviews

Vacation Home In Millerton

SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Guest favorite
Home in Monroe
4.93 out of 5 average rating, 14 reviews

The Camp

BrendaRating, 5 stars2 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Top guest favorite
A bright dining area features a round white table with metal chairs, positioned near large glass doors that open to a snowy outdoor view. Natural light fills the space, complemented by light-colored walls and a modern pendant light overhead.
Home in Great Barrington
5 out of 5 average rating, 6 reviews

Summer & Leaf Season Rental!

AnnieRating, 5 stars3 months ago
What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!
Guest favorite
A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.
Home in Woodstock
4.92 out of 5 average rating, 470 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

NiharRating, 5 stars1 week ago
fantastic host and super helpful whenever we had questions. my wife left her iPad there and they mailed it back. verry appreciative of that. first time using a wood fired sauna- I was skittish at first, but it was a great amenity. hot tub was clean and worked well as well. would definitely recommend if you're eyeing a rustic retreat.
Top guest favorite
A spacious outdoor deck features black lounge chairs set beside a low wooden table. A contemporary black chiminea stands as a focal point, surrounded by trees and open land, creating a relaxing atmosphere for outdoor gatherings.
Home in Athens
5 out of 5 average rating, 16 reviews

Lake house with arcade games

AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favorite
An open living area is highlighted by tall wooden beams and large windows allowing natural light to fill the space. A bar with stools complements the inviting seating area, which features a comfortable sofa and light decor against vibrant green walls.
Villa in Pownal
4.94 out of 5 average rating, 69 reviews

Vermont Vacation Villa—Grapevine Getaway

CindyRating, 5 stars2 months ago
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)
Guest favorite
An open living area features high ceilings with wooden beams and large windows allowing natural light. A neutral-toned couch and armchair provide seating, while a colorful area rug adds warmth. A staircase leads to an upper level, and a flat-screen TV is mounted on the wall.
Home in Woodstock
4.95 out of 5 average rating, 136 reviews

Woodstock Secluded Close to Town

JamienRating, 5 stars1 week ago
They were very friendly with very well laid out labels and instructions. Beautiful view with a very private location. so nice to have a hot tub next to the private woods.

Quick stats about vacation rentals in West Stockbridge

  • Total rentals

    70 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Frequently Asked Questions

  • How much does it cost to stay in house rentals in West Stockbridge?

    Experience the best of West Stockbridge with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in West Stockbridge?

    Yes! Work meets play with ease at over 30 house rentals in West Stockbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in West Stockbridge?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 50 homes with wifi, over 20 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in West Stockbridge have wifi?

    Absolutely! We offer over 50 house rentals with wifi in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Stockbridge have a gym?

    Absolutely! We offer over 10 house rentals with a gym in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Stockbridge have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in West Stockbridge have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in West Stockbridge. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in West Stockbridge?

    Four-legged friends are welcome in West Stockbridge. Choose from more than 20 house rentals for guests traveling with pets.

Destinations to explore