House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Great Barrington house rentals
House rentals with a hot tub
Home in Catskill
4.96 out of 5 average rating, 136 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Home in Craryville
4.98 out of 5 average rating, 189 reviewsModern Home in Woods w/ Hot Tub 10 Miles to Hudson
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Otis
4.85 out of 5 average rating, 164 reviewsThe Meadows House @ Otis Ridge w/ 7-person hot tub
Home in Hudson
4.95 out of 5 average rating, 250 reviewsLivingston Farmhouse Escape with hot tub and sauna
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Home in Saugerties
4.94 out of 5 average rating, 109 reviewsWaterfront Three bedroom in Saugerties w/ Hot Tub
House rentals with free parking
Home in Great Barrington
4.93 out of 5 average rating, 107 reviewsFormer Sunset View Inn
Home in Rhinebeck
4.91 out of 5 average rating, 256 reviewsArchitectural wonder in the woods
Home in Lee
4.9 out of 5 average rating, 206 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Dalton
4.88 out of 5 average rating, 114 reviewsThe Yellow House
Home in Great Barrington
4.9 out of 5 average rating, 111 reviewsYour own private Berkshires retreat
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Home in Canaan
5.0 out of 5 average rating, 135 reviewsCountry Cottage
Home in Great Barrington
4.96 out of 5 average rating, 114 reviewsModern Victorian on the Hill
House rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Home in Hudson
4.95 out of 5 average rating, 112 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
Home in Catskill
4.93 out of 5 average rating, 164 reviewsThe Grandview | Catskill, NY
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Home in Saugerties
4.92 out of 5 average rating, 119 reviewsRedbarn House | Pool | Fire Pit | HITS | 4 BR
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Quick stats about house rentals in Great Barrington
Total rentals
150 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
R923 ZAR before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Catskill Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Townhouse rentals United States
- Lighthouse rentals United States
- Earth house rentals United States
- House rentals United States
- Guesthouse rentals United States
- Townhouse rentals Long Island
- Tiny house rentals Long Island
- House rentals Long Island
- Guesthouse rentals Long Island
- Beach house rentals Long Island
- Townhouse rentals New York
- Treehouse rentals New York
- Guesthouse rentals New York
- House rentals New York
- Tiny house rentals New York
- Lakehouse rentals Massachusetts
- Guesthouse rentals Massachusetts
- Townhouse rentals Massachusetts
- Tiny house rentals Massachusetts
- House rentals Massachusetts
- Beach house rentals Massachusetts
- Rentals with a hot tub Great Barrington
- Pet-friendly rentals Great Barrington
- Rentals with a fire pit Great Barrington
- Apartment rentals Great Barrington
- Fitness-friendly rentals Great Barrington
- Waterfront rentals Great Barrington
- Rentals with a kayak Great Barrington
- Rentals with a washer and dryer Great Barrington
- Rentals with a fireplace Great Barrington
- Rentals with pools Great Barrington
- Rentals with outdoor seating Great Barrington
- Rentals with a patio Great Barrington
- Kid-friendly rentals Great Barrington
- Rentals with lake access Great Barrington
- Cabin rentals Great Barrington
- Family-friendly rentals Great Barrington
- Monthly Rentals Great Barrington
- Guesthouse rentals Berkshire County
- House rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom