
House holiday rentals in Great Barrington
Find and book unique houses on Airbnb
Top-rated house rentals in Great Barrington
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.

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.

Best of the Berkshires + Hot Tub by Evergreen Home
Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Belle Meade
Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

GB at your doorstep
Our home is in the heart of vibrant downtown Great Barrington, just steps from the River Walk. Stroll a block to the vibrant shops, eateries, farmer's market, and historic Mahaiwe Theater. It's a quick 20 minute drive to the world class music at Tanglewood and the theater productions at Shakespeare & Co. Winter sports enthusiasts will be 5 minutes to Ski Butternut and 15 minutes to Catamount Ski Mountain. Relaxation at Lake Mansfield is only minutes away by car.

HOT TUB! Berkshires: Dog & Family Friendly!
Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

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.

Walk to Town! Great Barrington 4-bedroom farmhouse
Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Swim Lake , Hikes, Sleeps 12, Fast WiFi
Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * 5 mins to Swim lake, kayaking & fishing. * Great Hikes from the house * Pets welcome * Jacobs Pillow & Tanglewood 20 mins * Historic Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Fast Wifi * Fireplace * Butternut ski 15 mins

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!

Architectural wonder in the woods
Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.

Prime location for the best of the Berkshires
Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.
Popular amenities for house rentals in Great Barrington
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4Br Mountain Brook House on 130 acres w/ trails

Highwoods Haven | saltwater pool and hot tub

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Hudson River Sunset Getaway

MODERN FARMHOUSE in the WOODS

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

Bull Hill Bungalow

Winter ski retreat minutes from Butternut

Seekonk Hill

Secluded + Modern | Enclosed Patio | Woodland Zen

Berkshires Black Abbey

Lovely house in the Berkshires

Sauna + Hot Tub Escape | Private & Pet Friendly

A Berkshires Abode - Minutes to Ski & Downtown GB!
Private house rentals

River Cottage: Riverfront Home, Walkable Community

Cozy cottage on peaceful pond

Charming Stockbridge Farmhouse- walk to town!

Jug End Crest | Fireplace • Sunroom • Central Air

The Catamount Ski Haus with Pool & Hot Tub

Hilltop Ski and Sun Chalet with Hot Tub

Renovated Downtown Great Barrington House

Berkshires Family Oasis with Hot Tub, Patio, Gym
When is the best time to visit Great Barrington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £271 | £271 | £259 | £261 | £282 | £301 | £336 | £327 | £270 | £285 | £282 | £301 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about house rentals in Great Barrington

Total holiday rentals
Explore 130 holiday rentals in Great Barrington

Nightly prices starting at
Great Barrington holiday rentals start at £23 per night before taxes and fees

Verified guest reviews
Over 4,760 verified reviews to help you choose

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Great Barrington holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Great Barrington rentals

4.9 Average rating
Great Barrington stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a firepit Great Barrington
- Rentals with outdoor seating Great Barrington
- Rentals with a hot tub Great Barrington
- Rentals with a patio Great Barrington
- Rentals with a kayak Great Barrington
- Rentals with a washing machine and dryer Great Barrington
- Rentals with a fireplace Great Barrington
- Flat rentals Great Barrington
- Pet-friendly rentals Great Barrington
- Waterfront rentals Great Barrington
- Family-friendly rentals Great Barrington
- Rentals with pools Great Barrington
- Fitness-friendly rentals Great Barrington
- Rentals with lake access Great Barrington
- Cabin rentals Great Barrington
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- House rentals United States
- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- June Farms
- Naumkeag
- Opus 40
- Berkshire Botanical Garden
- Walkway Over the Hudson State Historic Park




