![](https://a0.muscache.com/im/pictures/d6ce61b5-87e5-4f45-b54d-42f2f7ef9a55.jpg)
Vacation home rentals in The Berkshires
Find and book unique vacation home rentals on Airbnb
Top-rated vacation home rentals in The Berkshires
Guests agree: these vacation home rentals 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 The Berkshires vacation home rentals
Family-friendly vacation home rentals
![](https://a0.muscache.com/im/pictures/5df85a04-8879-436c-93b6-ddb994e01879.jpg?im_w=720)
Vacation home in Halcott
4.51 out of 5 average rating, 179 reviewsA Frame in the Mountains with Hot tub + Fast Net
![](https://a0.muscache.com/im/pictures/0c62a573-f62e-486c-8b69-309fba3d636c.jpg?im_w=720)
Vacation home in Cairo
4.65 out of 5 average rating, 23 reviewsChalet on the Hill
![](https://a0.muscache.com/im/pictures/miso/Hosting-52946368/original/6209bf87-1b12-4cd1-8fe7-f5244c28cf08.jpeg?im_w=720)
Vacation home in Hudson
4.82 out of 5 average rating, 102 reviewsGreat top fl near cnter with sunroom and a view cc
![](https://a0.muscache.com/im/pictures/miso/Hosting-52946570/original/fb0913a2-917b-4c53-aeed-6552fa874f8a.jpeg?im_w=720)
Vacation home in Hudson
4.82 out of 5 average rating, 71 reviews2 blocks to Warren ST with an office and a yard cb
![](https://a0.muscache.com/im/pictures/miso/Hosting-53074343/original/fa665391-d5dc-40cc-9987-a699f7a41bdd.jpeg?im_w=720)
Vacation home in Hudson
4.76 out of 5 average rating, 63 reviews2 blocks to Warren ST with Backyard,& Parking
![](https://a0.muscache.com/im/pictures/miso/Hosting-52730613/original/abf25e53-46ee-4333-9daa-43918f22690c.jpeg?im_w=720)
Vacation home in Hudson
4.86 out of 5 average rating, 95 reviews3 block to Warren ST with a Yard and parking ga
![](https://a0.muscache.com/im/pictures/miso/Hosting-52730738/original/d9a19b86-3cac-41d6-b4f4-d83ce52f602c.jpeg?im_w=720)
Vacation home in Hudson
4.94 out of 5 average rating, 85 reviews2BRT 3 blocks to Warren ST
![](https://a0.muscache.com/im/pictures/miso/Hosting-52946774/original/3275d956-7a43-4a27-871b-eaf008276911.jpeg?im_w=720)
Vacation home in Hudson
4.91 out of 5 average rating, 87 reviews2 blocks to Warren ST w/ a yard and parking
Vacation home rentals with a patio
![](https://a0.muscache.com/im/pictures/miso/Hosting-597149749614200213/original/5af783aa-eb93-4374-8235-04d7f24dacea.jpeg?im_w=720)
Vacation home in Beacon
5 out of 5 average rating, 53 reviewsPrivate, modern carriage house. Great for couples.
![](https://a0.muscache.com/im/pictures/miso/Hosting-657778574280914637/original/b47d1a73-ede1-4e2f-adc7-b70166522beb.jpeg?im_w=720)
Vacation home in Salt Point
4.88 out of 5 average rating, 41 reviewsRiverfront, cozy farmhouse near Rhinebeck
![](https://a0.muscache.com/im/pictures/ca90a5d2-2b70-4ed5-9fa9-9ccc37ebf18d.jpg?im_w=720)
Vacation home in East Hampton
5 out of 5 average rating, 29 reviewsFamily Friendly Lake House Lake Pocotopaug Sunsets
![](https://a0.muscache.com/im/pictures/miso/Hosting-641199119582509239/original/c133fa14-4ce0-4ab1-8560-25582c0ade40.jpeg?im_w=720)
Vacation home in Putnam Valley
4.91 out of 5 average rating, 23 reviewsHudson Valley Glass-sided Lakehouse
![](https://a0.muscache.com/im/pictures/miso/Hosting-760752747453214361/original/b70509f4-3610-4748-9d5f-354bd5fa4312.jpeg?im_w=720)
Vacation home in Town of Rockingham
4.96 out of 5 average rating, 55 reviewsCozy studio at Leslie's Tavern in Rockingham
![](https://a0.muscache.com/im/pictures/miso/Hosting-753698455508925098/original/bb2ee33d-5419-4f92-b357-432488656fc2.jpeg?im_w=720)
Vacation home in Litchfield County
4.93 out of 5 average rating, 14 reviewsPacer's Pasture
![](https://a0.muscache.com/im/pictures/miso/Hosting-649073768681195965/original/663b3f29-8654-4afc-8a5b-03bd3419679f.jpeg?im_w=720)
Vacation home in Windham
4.93 out of 5 average rating, 61 reviews*Farmhouse Chic with Mountain and Lake Views*
![](https://a0.muscache.com/im/pictures/miso/Hosting-717333902679262571/original/2a23c975-f0cd-4f85-b2be-cb29c8d15eb4.jpeg?im_w=720)
Vacation home in Ulster Park
4.9 out of 5 average rating, 20 reviewsWeeping Willow Hideaway on the Lake Studio Suite
Vacation home rentals with a washer and dryer
![](https://a0.muscache.com/im/pictures/e96b73dd-34d9-438c-a97a-3dadd8da1dc5.jpg?im_w=720)
Vacation home in Becket
4.95 out of 5 average rating, 43 reviewsPerfect Serene Waterfront All Season Retreat!
![](https://a0.muscache.com/im/pictures/miso/Hosting-655885477667449287/original/b4ee9c3f-0136-4da4-ba7d-def54990dabf.jpeg?im_w=720)
Vacation home in Otis
5 out of 5 average rating, 11 reviewsSunny oasis in the woods in Otis
![](https://a0.muscache.com/im/pictures/miso/Hosting-49324314/original/de45f1a7-4895-40dd-a89d-ca34290c7f5a.jpeg?im_w=720)
Vacation home in Brewster
4.94 out of 5 average rating, 53 reviewsScandi Peaceful Oasis, Private Pool, Hottub!
![](https://a0.muscache.com/im/pictures/miso/Hosting-2871489/original/1846dff5-8d3d-4db0-bb70-9709feeee417.jpeg?im_w=720)
Vacation home in Athens
4.92 out of 5 average rating, 78 reviewsLakefront Retreat | Kayaks, Paddle Board & Hot tub
![](https://a0.muscache.com/im/pictures/miso/Hosting-50301735/original/025ec1f1-75da-4599-98d4-a08ad99cf6b3.jpeg?im_w=720)
Vacation home in Hadley
5 out of 5 average rating, 19 reviewsEntire House-Sacandaga Lakeview Home on Rosebloom
![](https://a0.muscache.com/im/pictures/miso/Hosting-749795556551899251/original/1bf93c56-e8bd-4474-b8af-1021294c12d9.jpeg?im_w=720)
Vacation home in Dover
4.87 out of 5 average rating, 23 reviewsWalk to Mount Snow, Cozy, Clean and Comfortable
![](https://a0.muscache.com/im/pictures/miso/Hosting-547056576513481842/original/502b047e-e371-4570-ad3e-9d4b659c5698.jpeg?im_w=720)
Vacation home in Napanoch
4.86 out of 5 average rating, 22 reviewsThe Swallow's Nest Catskills with pool & firepit
![](https://a0.muscache.com/im/pictures/miso/Hosting-622630134645873417/original/e25b99f9-9c21-4f20-a79c-346fad4f1a64.jpeg?im_w=720)
Vacation home in Gardiner
5 out of 5 average rating, 21 reviewsCountry oasis on 75 acres with pond and hiking
Destinations to explore
- Vacation home rentals United States
- Vacation home rentals New York
- Vacation home rentals Long Island
- Rentals with a washer and dryer The Berkshires
- Pet-friendly rentals The Berkshires
- Waterfront rentals The Berkshires
- Rentals with a hot tub The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Lakehouse rentals The Berkshires
- Cabin rentals The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Rentals with a sauna The Berkshires
- Fitness-friendly rentals The Berkshires
- Cottage rentals The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- Rentals with an EV charger The Berkshires
- Smoking-friendly rentals The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Rentals with a kayak The Berkshires
- Rentals with pools The Berkshires
- Monthly Rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Aparthotel rentals The Berkshires
- Townhouse rentals The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Rentals with a patio The Berkshires
- Rentals with breakfast The Berkshires
- Farmstay rentals The Berkshires
- Rentals with a fire pit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Kid-friendly rentals The Berkshires
- Rentals with a home theater The Berkshires
- Wheelchair accessible rentals The Berkshires
- Rentals with outdoor seating The Berkshires
- House rentals The Berkshires
- Rentals with beach access 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