
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
Get the amount of space that is right for you
Popular amenities for hotel rentals in Berkshire County
Family-friendly hotel rentals

Sheffield Lodge - Monument Room

Sheffield Lodge - Greylock Room

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

Cozy 2-bedroom apartment with AC, fitness room
Hotel rentals with a pool

New England Landmark + 4 Dining Spots Onsite. Pool

Great place|2 BD|Kitchen| Pool

Great Place |2 BD|Kitchen| Pool

Great Place|2 BD|Kitchen| Pool

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

Great place|2 BD|Kitchen| Pool

Great Place - 2BD/2BA

Little Cat Lodge - Double Double
Hotel rentals with a patio

Great place|2 BD|Kitchen| Pool

Great place|2 BD|Kitchen| Pool

Great Place|2 BD|Kitchen| Pool

Home a while

Great for family|2 BD|Kitchen| Pool

Wyndham Bentley Brook * 1 Bedroom

Near all lodging alternative cln

Great place|2 BD|Kitchen| Pool
Destinations to explore
- Rentals with a patio Berkshire County
- Ski-in/ski-out rentals Berkshire County
- Bed and breakfasts Berkshire County
- House rentals Berkshire County
- Pet-friendly rentals Berkshire County
- Beachfront rentals Berkshire County
- Aparthotel rentals Berkshire County
- Rentals with a firepit Berkshire County
- Fitness-friendly rentals Berkshire County
- Waterfront rentals Berkshire County
- Rentals with an EV charger Berkshire County
- Rentals with a sauna Berkshire County
- Rentals with lake access Berkshire County
- Family-friendly rentals Berkshire County
- Rentals with a washing machine and dryer Berkshire County
- Cottage rentals Berkshire County
- Rentals with a kayak Berkshire County
- Rentals with pools Berkshire County
- Rentals with breakfast Berkshire County
- Farm stay rentals Berkshire County
- Rentals with beach access Berkshire County
- Flat rentals Berkshire County
- Cabin rentals Berkshire County
- Rentals with a hot tub Berkshire County
- Rentals with a fireplace Berkshire County
- Chalet rentals Berkshire County
- Guest house rentals Berkshire County
- Apartment rentals Berkshire County
- Rentals with outdoor seating Berkshire County
- Private suite rentals 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
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Taconic State Park
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Sugarloaf State Reservation
- Hartford Golf Club
- Hancock Shaker Village
- Northern Cross Vineyard
- Opus 40
- Albany Center Gallery
- Talcott Mountain State Park
- Bright Nights at Forest Park