
Holiday home rentals in The Berkshires
Find and book unique holiday home rentals on Airbnb
Top-rated holiday home rentals in The Berkshires
Guests agree: these holiday home rentals 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 holiday home rentals in The Berkshires
Family-friendly holiday home rentals

3 block to Warren ST with a Yard and parking ga

Bright and Airy 2 blocks from Warren ST eb

Chalet on the Hill

2 blocks to Warren ST w/ a yard and parking

2BRT 3 blocks to Warren ST

2 blocks to Warren ST with an office and a yard cb
Holiday home rentals with a patio

Modern Coastal Home with Pool

La Maison Hudson: Charming 1BR In Prime Location

Once in a Lifetime Hudson River Views

Cozy Glens Falls home near Lake George & Saratoga

Charming Vacation House w/ Pool & HotTub

Cozy Catskills retreat w/views & fireplace

Riverfront, cozy farmhouse near Rhinebeck

UNIQUE and GORGEOUS historic loft style rental
Holiday home rentals with a washing machine and dryer

Mountain escape in Hunter/Tannersville

Modern HOT TUB House 3mins to Belleayre

Lake View w/ Pickleball Court

Perfect Serene Waterfront All Season Retreat!

Walk to town, Marina Views, Greenport Village

Explore the Berkshires from this charming home.

Large elegant 2BR in Village walk to restaurants!

The Barn Loft- Spacious stream-side Catskill home
Destinations to explore
- Waterfront rentals The Berkshires
- Townhouse rentals The Berkshires
- Smoking-friendly rentals The Berkshires
- Rentals with a hot tub The Berkshires
- Fitness-friendly rentals The Berkshires
- Rentals with a cinema The Berkshires
- Rentals with outdoor seating The Berkshires
- Cabin rentals The Berkshires
- Rentals with a firepit The Berkshires
- Guest house rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Rentals with an accessible-height toilet The Berkshires
- Rentals with an EV charger The Berkshires
- Family-friendly rentals The Berkshires
- Private suite rentals The Berkshires
- House rentals The Berkshires
- Rentals with beach access The Berkshires
- Chalet rentals The Berkshires
- Apartment rentals The Berkshires
- Lakehouse rentals The Berkshires
- Flat rentals The Berkshires
- Hotel rentals The Berkshires
- Cottage rentals The Berkshires
- Aparthotel rentals The Berkshires
- Rentals with pools The Berkshires
- Rentals with breakfast The Berkshires
- Boutique hotel rentals The Berkshires
- Villa rentals The Berkshires
- Rentals with a kayak The Berkshires
- Pet-friendly rentals The Berkshires
- Rentals with a washing machine and dryer The Berkshires
- Farm stay rentals The Berkshires
- Rentals with a sauna The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Rentals with a patio The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Family-friendly rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Holiday home rentals United States
- 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