Cottage vacation rentals in Western Massachusetts
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Western Massachusetts
Guests agree: these cottages 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 cottage rentals
Cottage rentals with a hot tub
Cottage in Great Barrington
4.93 out of 5 average rating, 236 reviewsArtist Cottage
Oct 21 – 28
Cottage in Ledyard
4.92 out of 5 average rating, 203 reviewsLakeside cottage with beautiful views up the lake!
Jan 14 – 21
Cottage in Phoenicia
4.89 out of 5 average rating, 800 reviewsRomantic hot tub cottage. Hiking/breweries nearby.
Sep 12 – 19
Cottage in Woodstock
4.9 out of 5 average rating, 376 reviewsFamous Architect - Streamside Cottage w/ hot tub
Oct 2 – 9
Cottage in Narragansett
5.0 out of 5 average rating, 188 reviews♥CozyGetaway-Narragansett-15min to Newport-HotTub♛
Mar 8 – 15
Cottage in Litchfield
4.89 out of 5 average rating, 258 reviewsLitchfield - Hot Tub - Mohawk Mountain - Fireplace
Jul 24 – 31
Cottage in Red Hook
4.92 out of 5 average rating, 324 reviewsGoose Landing Cottage by the lake with NEW Hot Tub
Mar 25 – Apr 1
Cottage in Kerhonkson
4.84 out of 5 average rating, 141 reviewsGunks Cottage|Fire Pit|Pool|Near Minnewaska Park
Dec 9 – 16
Pet-friendly cottage rentals
Cottage in North Bennington
4.9 out of 5 average rating, 290 reviewsRomantic Private Vermont Cottage - Waterfront
Jul 18 – 25
Cottage in Saugerties
4.93 out of 5 average rating, 217 reviewsChic & Cozy Cottage 10 mins to Woodstock
Aug 1 – 8
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Nov 1 – 8
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
Jul 22 – 29
Cottage in Red Hook
4.98 out of 5 average rating, 598 reviewsbright serene + spacious barn
Nov 14 – 21
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
May 1 – 8
Cottage in Scituate
4.9 out of 5 average rating, 197 reviews5 Star cottage in historical Clayville
Oct 6 – 13
Cottage in Gilboa
4.94 out of 5 average rating, 200 reviewsHome Alone Mountain Retreat
Nov 6 – 13
Private cottage rentals
Cottage in Shaftsbury
4.96 out of 5 average rating, 111 reviewsRollin Cottage
Sep 26 – Oct 3
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Oct 22 – 29
Cottage in Shutesbury
4.93 out of 5 average rating, 196 reviewsLake Wyola House Shutesbury Massachusetts
Aug 12 – 19
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone School Cottage
Sep 23 – 30
Cottage in Accord
4.88 out of 5 average rating, 216 reviewsSweet Cottage on a Farm Road
May 11 – 18
Cottage in Woodstock
4.99 out of 5 average rating, 277 reviewsGrapevine Cottage
Apr 19 – 26
Cottage in Saugerties
4.93 out of 5 average rating, 217 reviewsNew:Cozy Barn-Style Retreat Minutes From Woodstock
Oct 18 – 25
Cottage in Voluntown
4.95 out of 5 average rating, 187 reviewsLakeside Cottage in the Forest
Dec 23 – 30
Destinations to explore
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Providence Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Cottage rentals Boston
- Cottage rentals New York
- Cottage rentals New Hampshire
- Cottage rentals Massachusetts
- Waterfront rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Farmstay rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Rentals with a home theater Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Condo rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Hotel rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- House rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Kid-friendly rentals Western Massachusetts
- Rentals with lake access Western Massachusetts
- Beachfront rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Monthly Rentals Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Vacation home rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with beach access Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Townhouse rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Private suite rentals Western Massachusetts
- Rentals with pools Western Massachusetts
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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