
Holiday rentals in Western Massachusetts
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Top-rated holiday rentals in Western Massachusetts
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Western Massachusetts holiday rentals
Other great holiday rentals in Western Massachusetts
Top guest favourite

Home in Belchertown
4.99 out of 5 average rating, 75 reviewsMoonstone Lake House – romantic, serene, fun!
Top guest favourite

Flat in Northampton
4.98 out of 5 average rating, 371 reviewsLight filled three bedroom apartment DT Florence!
Guest favourite

Campervan/Motorhome in Westhampton
4.88 out of 5 average rating, 176 reviewsAirbytheStream waterfront, private, clean and cozy
Guest favourite

Home in Becket
4.96 out of 5 average rating, 28 reviewsNew Shaw Pond Skytop Retreat in the Berkshires
Top guest favourite

Guest house in Guilford
5 out of 5 average rating, 41 reviewsPeaceful forest cottage getaway
Superhost

Home in Great Barrington
5 out of 5 average rating, 3 reviewsBerkshires Black Abbey
Guest favourite

Home in Lanesborough
4.96 out of 5 average rating, 52 reviewsHistoric Stone Church in The Berkshires
Top guest favourite

Farm stay in Worthington
4.97 out of 5 average rating, 36 reviewsLike sleeping on a cloud
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Montreal Holiday rentals
- South Jersey Holiday rentals
- Cottage rentals Western Massachusetts
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- Rentals with a sauna Western Massachusetts
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- Hotel rentals Western Massachusetts
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- Rentals with a fireplace Western Massachusetts
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- Tiny house rentals Western Massachusetts
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- Rentals with a washing machine and dryer Western Massachusetts
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- Boutique hotel rentals Western Massachusetts
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- Rentals with a kayak Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Farm stay rentals Western Massachusetts
- Rentals with an accessible-height toilet Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
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- Six Flags New England
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hancock Shaker Village