House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Berkshire County house rentals
House rentals with a pool
Home in Sheffield
Race Mountain House
Home in Sheffield
Private Berkshire County Retreat
Home in Cheshire
Berkshire County modern home + pool
Home in Great Barrington
Berkshire Country Estate! Pool & Tennis Court -GB
Home in Egremont
Catamount House w. Pool/Hot Tub
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
Home in Lee
Berkshire Vacation Home in Lee (Pool is Open!)
Home in West Stockbridge
Heated Pool, Screened Porch, Gardens, Sleeps 13!
Weekly house rentals
Home in Huntington
Private house on the River
Home in Egremont
The Berkshires Mountain Terrace LUX Home Sleeps 7
Home in Sheffield
A Private Peninsula Retreat In The Berkshires!
Home in New Marlborough
Lake House in the Berkshire (Access Dock & Canoe
Home in Becket
Nerd Preservation Sanctuary
Home in Berlin
Cozy, 1779 Farmhouse, Upstate NY
Home in Sandisfield
Design Cottage on a Trout River. Fly Fishing Spot!
Home in Lee
GreenHouse
Private house rentals
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
Home in Adams
Mountain View Hideaway
Home in Pittsfield
Charming lake house with amazing sunset views
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
Home in Cheshire
The Berkshires Hummingbird House
Home in Great Barrington
Quiet home on the hill.
Home in West Stockbridge
Beautiful And Private Home Centrally Located
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
Destinations to explore
- Earth house rentals United States
- Lighthouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Townhouse rentals United States
- Treehouse rentals New York
- Townhouse rentals New York
- Tiny house rentals New York
- House rentals New York
- Guesthouse rentals New York
- Guesthouse rentals Massachusetts
- Lake house rentals Massachusetts
- Beach house rentals Massachusetts
- Tiny house rentals Massachusetts
- House rentals Massachusetts
- Townhouse rentals Massachusetts
- Guesthouse rentals Massachusetts
- Lake house rentals Massachusetts
- Beach house rentals Massachusetts
- Tiny house rentals Massachusetts
- House rentals Massachusetts
- Townhouse rentals Massachusetts
- Hotel rentals Berkshire County
- Rentals with a patio Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Fitness-friendly rentals Berkshire County
- Condo rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Beachfront rentals Berkshire County
- Rentals with lake access Berkshire County
- Rentals with breakfast Berkshire County
- Monthly Rentals Berkshire County
- Rentals with pools Berkshire County
- Waterfront rentals Berkshire County
- Farmstay rentals Berkshire County
- Rentals with a kayak Berkshire County
- Apartment rentals Berkshire County
- Private suite rentals Berkshire County
- Kid-friendly rentals Berkshire County
- Rentals with a firepit Berkshire County
- Bed and breakfasts Berkshire County
- Pet-friendly rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with beach access Berkshire County
- Rentals with an EV charger Berkshire County
- Guesthouse rentals Berkshire County
- Chalet rentals Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washer and dryer Berkshire County
- Cottage rentals Berkshire County
- Boutique hotel rentals Berkshire County
- Rentals with a sauna 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