Western Massachusetts vacation rentals
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Top-rated vacation rentals in Western Massachusetts
Guests agree: these vacation rentals 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 Western Massachusetts vacation rentals
Western Massachusetts fishing vacation rentals
Cottage in North Bennington
Romantic Private Vermont Cottage - Waterfront
Cottage in Becket
Cozy lakeside cottage
Cabin in Petersburg
Cozy Retreat in the Trees
Cottage in Ashfield
hope house
Home in New Lebanon
The old sawmill from 1771
Home in Monterey
Charming cottage w/ gorgeous views.
Rental unit in Great Barrington
Private En Suite in Beautiful Victorian
Home in Southwick
Linny's Lakeview Cottage
House rentals in Western Massachusetts
Home in Chester
Riverfront Getaway
Home in Dalton
The Yellow House
Home in Williamsburg
Hilltown Studio
Home in Pownal
Cozy Vermont mini-house
Home in Northampton
Discover Cozy Elegance in the Heart of Northampton
Home in Great Barrington
Jaw dropping mountain & lake views
Home in Feeding Hills
Farm Fresh Feeding Hills
Home in Bennington
Cozy Modern Sugar House with spectacular views.
Lakefront house rentals in Western Massachusetts
Home in Catskill
HEAVEN ON EARTH - Hudson Riverfront Home
Home in Wappingers Falls
Tranquil Tree-House on the beautiful Hudson River
Home in Becket
Lake front retreat - Stylish Berkshire home
Home in Woodstock
Woodstock Historic Artist Estate - The Pond House
Home in East Haddam
Romantic Getaway at The Lake!
Home in Vernon
Luxe Bolton Lake!
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
Home in Preston
New Lake Front Home w/ Game Room & Stunning Views
Destinations to explore
- Cambridge Vacation rentals
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- Farmstay rentals Western Massachusetts
- House rentals Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Aparthotel rentals Western Massachusetts
- Condo rentals Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Monthly Rentals Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Cottage rentals Western Massachusetts
- Rentals with beach access Western Massachusetts
- Cabin rentals Western Massachusetts
- Townhouse rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Waterfront rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with a patio Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Private suite rentals Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Hotel rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Loft rentals Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Kid-friendly rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Vacation home rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
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- Family travel hub Tips and inspiration
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