
Holiday houses in Berkshire County
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Berkshire County
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County holiday rentals
Other great holiday rentals in Berkshire County
Superhost

Apartment in Great Barrington
4.78 out of 5 average rating, 18 reviewsWriter's retreat: study, books, fireplace (Ecobnb)
Superhost

Apartment in Chester
4.76 out of 5 average rating, 191 reviewsQuiet getaway in the Berkshires
Guest favourite

Home in Egremont
5 out of 5 average rating, 22 reviewsThe Catamount Ski Haus w. Pool/Hot Tub
Guest favourite

Home in Lanesborough
5 out of 5 average rating, 14 reviewsBerkshire Mountain House
Guest favourite

Home in Otis
4.92 out of 5 average rating, 151 reviewsThe Pinnacle House at Otis Ridge Ski Area!
Superhost

Villa in South Lee
4.79 out of 5 average rating, 122 reviewsVilla with Access to Amazing Amenities!
Guest favourite

Cottage in Lanesborough
4.97 out of 5 average rating, 64 reviewsAmazing 2 bedroom lake front cottage, large patio
Superhost

Apartment in New Lebanon
4.79 out of 5 average rating, 14 reviewsA Sacred Place
Destinations to explore
- Kid-friendly rentals Berkshire County
- Rentals with lake access Berkshire County
- Waterfront rentals Berkshire County
- Rentals with beach access Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Private suite rentals Berkshire County
- Rentals with a patio Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Beachfront rentals Berkshire County
- Monthly Rentals Berkshire County
- Guesthouse rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Rentals with pools Berkshire County
- Rentals with a sauna Berkshire County
- Apartment rentals Berkshire County
- Chalet rentals Berkshire County
- Farmstay rentals Berkshire County
- House rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with an EV charger Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with a fire pit Berkshire County
- Cottage rentals Berkshire County
- Rentals with breakfast Berkshire County
- Rentals with a kayak Berkshire County
- Bed and breakfasts 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
- Things to do United States
- Sightseeing United States
- Nature and outdoors United States
- Sports activities United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Wellness United States
- Things to do Massachusetts
- Food and drink Massachusetts
- Art and culture Massachusetts
- Sightseeing Massachusetts
- Nature and outdoors Massachusetts
- Things to do Berkshire County