
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 ﺩ.ﺇ 257 per night before taxes and fees

Verified guest reviews
Over 1,680 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.

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 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE 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 a exciting, romantic and unique experience. The space can also comfortably 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.

Casa Luna Country Retreat with Pool, Hudson, NY
CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

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.

Windswept! 3 Queen 2 BA NEW Outdoor Sauna & Shower
Welcome to Windswept Acres! -A 12 acre pastural mountain top setting with a Norwegian Inspired OUTDOOR 4 person SAUNA and SHOWER!. 3 BR 2 bath, fully equipped kitchen, dining room, 2 living rooms, a cozy pellet stove for added warmth on those chilly Fall/Winter evenings. WIFI for those working remotely. A great friend/family gathering place for those between NYC and Boston! Please see host and guest interaction access in information for guest section.

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.

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy
38 beautiful, private acres of Berkshire woods, cleared land, and mountain scenery. 6 comfortable bedrooms and 4.5 bathrooms. 9 Minutes from Jiminy Peak Ski Resort. 5 Mins from The Lake House cottages. Warm and cozy, modern gem. 4 Fireplaces, multiple hang out areas, napping areas, sauna, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

Chatham on the Creek. Pet friendly. F Trump
This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

Designer Home, Hot Tub, Private Yard, & Projector
A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

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

Private lakefront home, hot tub & resort amenities

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

4Br Mountain Brook House on 130 acres w/ trails

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Hudson River views with pool and hot tub

Catskill Retreat: Heated Pool, Hot Tub, Sauna!
Weekly house rentals

Bright, Airy Home in Hudson w/ TONS of Character!

Berkshires Forest Retreat with Hot Tub

Exceptional Stockbridge Retreat

The Stone House

Rustic Swedish Barn/Featured in Airbnb Magazine

Pixley Forest | 15 Mins To Tanglewood • Fireplace
Stylish Hawthorne Valley Farmhouse Retreat

Modern Log Cabin w/Pool & Views By Evergreen Home
Private house rentals

Crossbridge Main House - Vintage Charm & Unique Ch

Private Artist's Retreat Berkshires Adjacent

Cozy cottage on peaceful pond

Bull Hill Bungalow

Secluded Post-and-Beam Chalet w/Breathtaking Views

Lake House in Copake

Cozy stylish Cabin in the Woods

Historic Stone Church in The Berkshires
When is the best time to visit West Stockbridge?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,194 | ﺩ.ﺇ 1,194 | ﺩ.ﺇ 1,083 | ﺩ.ﺇ 918 | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 1,282 | ﺩ.ﺇ 1,333 | ﺩ.ﺇ 1,377 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 1,205 | ﺩ.ﺇ 1,190 | ﺩ.ﺇ 1,083 |
| 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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- Family-friendly rentals West Stockbridge
- Rentals with a fireplace West Stockbridge
- Rentals with a fire pit West Stockbridge
- Rentals with a washer and dryer West Stockbridge
- Rentals with a patio West Stockbridge
- Pet-friendly rentals West Stockbridge
- Rentals with outdoor seating West Stockbridge
- House rentals Berkshire County
- House rentals Massachusetts
- House rentals United States
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- June Farms
- Bash Bish Falls State Park
- Thacher State Park
- Zoom Flume
- Taconic State Park
- Bousquet Mountain Ski Area
- Hunter Mountain Resort
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Ski Sundown
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Millbrook Vineyards & Winery
- University of Massachusetts Amherst
- Naumkeag
- Norman Rockwell Museum
- MVP Arena





