The Berkshires vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in The Berkshires
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires vacation rentals
The Berkshires house rentals
Guest favorite
Home in Lee
4.9 out of 5 average rating, 208 reviews1817 Berkshire Farmhouse- Close to Everything.
Guest favorite
Home in Germantown
4.95 out of 5 average rating, 365 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Guest favorite
Home in Germantown
4.96 out of 5 average rating, 261 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Guest favorite
Home in Catskill
4.96 out of 5 average rating, 139 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Guest favorite
Home in Rhinebeck
5.0 out of 5 average rating, 165 reviewsEagle Rock House
Guest favorite
Home in New Paltz
4.97 out of 5 average rating, 683 reviewsVictorian Haven
Guest favorite
Home in Cornwall
4.92 out of 5 average rating, 231 reviewsSecluded modern forest cabin with private brook
Guest favorite
Home in Chester
4.96 out of 5 average rating, 314 reviewsRiverfront Getaway
Other great vacation rentals in The Berkshires
Guest favorite
Farm stay in Ancram
4.96 out of 5 average rating, 268 reviewsRelaxing secluded stay with loving social animals.
Guest favorite
Apartment in Sheffield
5.0 out of 5 average rating, 323 reviewsHideaway with Spectacular Berkshire Views
Guest favorite
Guesthouse in Lenox
4.95 out of 5 average rating, 288 reviewsThe Granary at House on Golden Hill
Guest favorite
Loft in Great Barrington
4.99 out of 5 average rating, 298 reviewsThe Old Red Barn
Guest favorite
Tiny home in New Paltz
4.99 out of 5 average rating, 745 reviewsHudson Valley Tiny House
Guest favorite
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 148 reviewsBeautiful Timber Frame Retreat
Guest favorite
Earthen home in West Sand Lake
4.98 out of 5 average rating, 153 reviewsThe Hobbit House at June Farms
Destinations to explore
- Wheelchair accessible rentals The Berkshires
- Rentals with beach access The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Rentals with a patio The Berkshires
- Farmstay rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Monthly Rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Pet-friendly rentals The Berkshires
- Waterfront rentals The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Rentals with a home theater The Berkshires
- Rentals with a washer and dryer The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Rentals with breakfast The Berkshires
- Rentals with a hot tub The Berkshires
- Townhouse rentals The Berkshires
- House rentals The Berkshires
- Rentals with a fire pit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Rentals with a kayak The Berkshires
- Rentals with pools The Berkshires
- Kid-friendly rentals The Berkshires
- Aparthotel rentals The Berkshires
- Lakehouse rentals The Berkshires
- Cabin rentals The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Boutique hotel rentals The Berkshires
- Cottage rentals The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Rentals with a sauna The Berkshires
- Rentals with outdoor seating The Berkshires
- 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