
Holiday Homes in The Berkshires
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in The Berkshires
Guests agree: These holiday homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires holiday homes
Family-Friendly holiday homes

Modern & Cozy Beach House - Walk to Ocean Beach

Large Private Estate! 28 Lots of beds, HotTub,Pool

Succurro : Studio

Cozy 1 bd Apt Minutes to Okemo & Pet Friendly

Cozy 2-Bedroom Vacation Home ăFree Wi-Fi & Parking

Perfect Windham getaway for year round fun!

The Loft - Discount Rates âŒïž Lake George.

5* Elegant 4 Bedroom by Beach; Minutes to Mystic
Holiday home rentals with a patio

âMulberry Guest HouseâPrivateâWalk to village

La Maison Hudson: Charming 1BR In Prime Location

Lake View w/ Pickleball Court

Once in a Lifetime Hudson River Views

The Dahlia Villa within Westerhall Gardens

Charming Vacation House w/ Pool & HotTub

Cozy Catskills retreat w/views & fireplace

Secluded hilltop getaway | heated pool + hot tub
Holiday home rentals with a washing machine and dryer

Mountain escape in Hunter/Tannersville

Modern HOT TUB House 3mins to Belleayre

Perfect Serene Waterfront All Season Retreat!

Saratoga Lakefront Belmont Travers 12 min to track

Walk to town, Marina Views, Greenport Village

Cozy Glens Falls home near Lake George & Saratoga

Explore the Berkshires from this charming home.

The Barn Loft- Spacious stream-side Catskill home
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- Apartment rentals The Berkshires
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- Waterfront rentals The Berkshires
- Chalet rentals The Berkshires
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- Rentals with a home theatre The Berkshires
- Rentals with a patio The Berkshires
- Cabin rentals The Berkshires
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- Holiday home rentals United States