
Hotel holiday rentals in Berkshire County
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Top-rated hotel rentals in Berkshire County
Guests agree: these hotel rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for hotel rentals in Berkshire County
Family-friendly hotel rentals

Sheffield Lodge - Monument Room

Sheffield Lodge

Catamount Lodging Ski In/Ski Out

Ultimate Mountain Access Catamount Ski In/Out

Cozy 2-bedroom apartment, AC in welcoming Lee

Cozy 2-bedroom apartment, in enjoyable Lee

Hidden Gem Next Door to Catamount - Ski In/Out

Cozy 2-bedroom apartment, WiFi in fabulous Lee
Hotel rentals with a pool

Great place|2 BD|Kitchen| Pool

★ Vintage Romance with Fireplace & Spa Tub

Great Place |2 BD|Kitchen| Pool

Great Place - Kitchen+Pool - 2BD

Great Place|2 BD|Kitchen| Pool

Berkshire Mass. Resort, 1bdrm 8/27-9/03 $1050

Heart of Stockbridge + Dining. Bike-Friendly. Pool

Great place|2 BD|Kitchen| Pool
Hotel rentals with a patio

Great place|2 BD|Kitchen| Pool

Great place|2 BD|Kitchen| Pool

Great Place|2 BD|Kitchen| Pool

Great for family|2 BD|Kitchen| Pool

Wyndham Bentley Brook * 1 Bedroom

Near all lodging alternative cln

Great place|2 BD|Kitchen| Pool

Great place|2 BD|Kitchen| Pool
Destinations to explore
- Flat rentals Berkshire County
- Rentals with lake access Berkshire County
- Waterfront rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Fitness-friendly rentals Berkshire County
- Beachfront rentals Berkshire County
- Private suite rentals Berkshire County
- Rentals with a firepit Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- House rentals Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Rentals with breakfast Berkshire County
- Guest house rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Rentals with a patio Berkshire County
- Chalet rentals Berkshire County
- Cottage rentals Berkshire County
- Aparthotel rentals Berkshire County
- Rentals with a fireplace Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with a kayak Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Rentals with pools Berkshire County
- Rentals with beach access Berkshire County
- Farm stay rentals Berkshire County
- Bed and breakfasts Berkshire County
- Hotel rentals Massachusetts
- Hotel rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Bushnell Park
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Wintonbury Hills Golf Course
- Norman Rockwell Museum
- Taconic State Park
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Opus 40
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Bright Nights at Forest Park
- Albany Center Gallery
- Bousquet Mountain Ski Area
- Berkshire Botanical Garden
- Mount Snow Ski Resort