House holiday rentals in Berkshire County
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Top-rated house rentals in Berkshire County
Guests agree: these houses 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 house rentals in Berkshire County
House rentals with a pool
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
Home in Cheshire
4.94 out of 5 average rating, 53 reviewsBerkshire County modern home + pool
Home in Great Barrington
4.97 out of 5 average rating, 35 reviewsBerkshire Country Estate! Pool & Tennis Court -GB
Home in West Stockbridge
4.97 out of 5 average rating, 62 reviewsPanoramic Views, Indoor Pool by Evergreen Home
Home in Great Barrington
5 out of 5 average rating, 54 reviewsStunning luxury home with pool
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Home in Hancock
5 out of 5 average rating, 6 reviewsBougie B's Mountainside Getaway
Home in Pittsfield
4.98 out of 5 average rating, 41 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Weekly house rentals
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Home in Egremont
4.96 out of 5 average rating, 106 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
Home in Becket
4.86 out of 5 average rating, 295 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Sheffield
4.93 out of 5 average rating, 111 reviewsA Private Peninsula Retreat In The Berkshires!
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
Home in Becket
4.95 out of 5 average rating, 42 reviewsNerd Preservation Sanctuary
Home in Stockbridge
4.94 out of 5 average rating, 98 reviewsBright Stockbridge country home, near everything!
Home in Lee
5 out of 5 average rating, 40 reviewsGreenHouse
Private house rentals
Home in Great Barrington
4.97 out of 5 average rating, 39 reviewsWaterfront Modern Lake Mansfield Retreat
Home in Becket
5 out of 5 average rating, 9 reviewsLakeside 3-BR Berkshires Residence
Home in West Stockbridge
5 out of 5 average rating, 20 reviewsBeautiful And Private Home Centrally Located
Home in Great Barrington
5 out of 5 average rating, 8 reviewsWalt's Townhouse - Berkshire living at its best
Home in Pittsfield
4.96 out of 5 average rating, 50 reviewsLake/Mountain View Getaway
Home in Lanesborough
5 out of 5 average rating, 92 reviewsTranquil mid-century modern Berkshires retreat
Home in Stockbridge
5 out of 5 average rating, 35 reviewsRelaxing Berkshire Retreat with Lake Access
Home in Cheshire
5 out of 5 average rating, 24 reviewsThe Berkshires Hummingbird House
Destinations to explore
- Earth house rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- Guest house rentals United States
- Tiny house rentals New York
- Treehouse rentals New York
- Townhouse rentals New York
- Guest house rentals New York
- House rentals New York
- Beach house rentals Massachusetts
- Guest house rentals Massachusetts
- House rentals Massachusetts
- Townhouse rentals Massachusetts
- Tiny house rentals Massachusetts
- Lakehouse rentals Massachusetts
- Beach house rentals Massachusetts
- Guest house rentals Massachusetts
- House rentals Massachusetts
- Townhouse rentals Massachusetts
- Tiny house rentals Massachusetts
- Lakehouse rentals Massachusetts
- Family-friendly rentals Berkshire County
- Waterfront rentals Berkshire County
- Rentals with lake access Berkshire County
- Pet-friendly rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Monthly Rentals Berkshire County
- Rentals with breakfast Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Rentals with pools Berkshire County
- Hotel rentals Berkshire County
- Rentals with a firepit Berkshire County
- Rentals with a patio Berkshire County
- Farm stay rentals Berkshire County
- Bed and breakfasts Berkshire County
- Private suite rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Beachfront rentals Berkshire County
- Chalet rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Guest house rentals Berkshire County
- Rentals with a kayak Berkshire County
- Cottage rentals Berkshire County
- Rentals with a sauna Berkshire County
- Boutique hotel rentals Berkshire County
- Rentals with beach access Berkshire County
- Rentals with an EV charger Berkshire County
- Flat rentals Berkshire County
- Rentals with a fireplace 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