
Vacation home rentals in Western Massachusetts
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Top-rated vacation home rentals in Western Massachusetts
Guests agree: these vacation home 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 home rentals
Family-friendly vacation home rentals

Chalet on the Hill

Ludlow Big Family Fun Home

2 blocks to Warren ST w/ a yard and parking

Great top fl near cnter with sunroom and a view cc

2 blocks to Warren ST with an office and a yard cb
Vacation home rentals with a patio

La Maison Hudson: Charming 1BR In Prime Location

Private, modern carriage house. Great for couples.

Once in a Lifetime Hudson River Views

Country oasis on 75 acres with pond and hiking

Cozy home near Lake George & Saratoga

Riverfront, cozy farmhouse near Rhinebeck

Secluded hilltop getaway | heated pool + hot tub

UNIQUE and GORGEOUS historic loft style rental
Vacation home rentals with a washer and dryer

Cozy Cabin in a Rural Setting #16

Perfect Serene Waterfront All Season Retreat!

Explore the Berkshires from this charming home.

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Large elegant 2BR in Village walk to restaurants!

Sunapee Barn Retreat

Sunny oasis in the woods in Otis
Destinations to explore
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- Cottage rentals Western Massachusetts
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Brimfield State Forest
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Rockledge Golf Club
- WIckham Park
- Things to do Western Massachusetts
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes