
House vacation rentals in West Stockbridge
Find and book unique houses on Airbnb
Quick stats about house rentals in West Stockbridge

Total vacation rentals
Explore 50 vacation rentals in West Stockbridge

Nightly prices starting at
West Stockbridge vacation rentals start at G$14,644 GYD per night before taxes and fees

Verified guest reviews
Over 1,600 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of West Stockbridge vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across West Stockbridge rentals

4.9 Average rating
West Stockbridge stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in West Stockbridge
Guests agree: these houses are highly rated for location, cleanliness, and more.

Bright Stockbridge country home, near everything!
Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Berkshire 4 season home
The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Berkshire Lakefront House with Amazing Views
Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

Rustic Swedish Barn/Featured in Airbnb Magazine
Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Peaceful Stockbridge Cabin in the Woods
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Jaw dropping mountain & lake views
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Chic Hudson Farmhouse w/ Fireplace & Porch
1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

Scandinavian Cottage/Mountain Views/Fire pit
A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Private Home in The Berkshires (New Hot Tub!)
Leave your worries and stress behind and enjoy all the beautiful Berkshires have to offer! This fully remodeled home is ready to serve as your new favorite vacation spot! Whether you’re looking to enjoy a laid back getaway or an adventurous stay, look no further. You’re a short 10 minute drive to Ski Butternut, less than 15 minutes to Catamount, and about 20 minutes away from Tanglewood Music Center!
Popular amenities for West Stockbridge house rentals
House rentals with a pool

4Br Mountain Brook House on 130 acres w/ trails

Hudson River Sunset Getaway

Viewtop Farmhouse-Relax & enjoy summer by the pool

Hudson River estate guest cottage

Casa Luna Country Retreat with Pool, Hudson, NY

Berkshire Getaway Ranch 3 acres + saltwater pool

Lake House close to Skiing & Indoor Hot Tub

Hudson getaway w/ hot tub+ plunge pool on 20 acres
Weekly house rentals

Greek Revival Farmhouse

Cantabile life in the Berkshires

Best of the Berkshires + Hot Tub by Evergreen Home
Stylish Hawthorne Valley Farmhouse Retreat

Livingston Farmhouse Escape with hot tub and sauna

The old sawmill from 1771

Charming cottage w/ gorgeous views.

Cozy lakehouse
Private house rentals

Pixley Forest | 15 Mins To Tanglewood • Fireplace

Exceptional Stockbridge Retreat

Cozy cottage on peaceful pond

Berkshires Forest Retreat with Hot Tub

Cozy stylish Cabin in the Woods

Crossings Cottage

Relaxing Retreat-Enjoy Hudson Valley & Berkshires

Stunning luxury home with pool
When is the best time to visit West Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$67,989 GYD | G$67,989 GYD | G$61,713 GYD | G$64,432 GYD | G$60,876 GYD | G$78,448 GYD | G$75,938 GYD | G$78,448 GYD | G$58,575 GYD | G$68,616 GYD | G$67,779 GYD | G$61,713 GYD |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
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- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- June Farms
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- University of Massachusetts Amherst
- MVP Arena
- Naumkeag
- New York State Museum
- Poets' Walk Park
- Massachusetts Museum of Contemporary Art





