
Vacation rentals in Cummington
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Top-rated vacation rentals in Cummington
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Other great vacation rentals in Cummington
Guest favorite

Cabin in Williamsburg
4.94 out of 5 average rating, 34 reviewsRetreat in the Woods
NicoleRating, 5 stars2 weeks ago
Our stay at Maya's place was lovely! We were visiting the area for a wedding and wanted to stay somewhere quiet, safe, and peaceful. This place was exactly what we were looking for! Maya was very responsive and the place was clean and cozy. It was super private, felt safe, and was very cozy! We would definitely come back to stay if we are in the area again!

Cabin in Plainfield
4.64 out of 5 average rating, 66 reviewsCamp on Windsor Pond- Berkshires
JenniferRating, 5 stars1 week ago
The cabin is in a beautiful location with the pond right across the street. It’s not a luxury stay but if you are just looking for a scenic location near the berkshires it is great.
Top guest favorite

Home in Cummington
5 out of 5 average rating, 12 reviewsRiver-front home in Berkshire hills w/tennis court
JenniferRating, 5 stars1 month ago
So grateful for our Peaceful escape into nature with detailed attention to pampering pleasures. This country charmer provided something for everyone throughout our gals getaway! The wooden hot tub, the crackling fire, the rushing river and all the beauty of the natural surroundings complimented by the most perfect clay tennis court for our tennis enthusiasts! Just 30 minutes from the hip artistic academic streets of downtown Northampton to the historic beauty of the potholes and bridge of flowers of Shelburne Falls To The Gorgeous Gorge of Chesterfield and the Tasty treats of The Old Cummington Co-Op all local musts! Comfy beds, cozy kitchen, and little nooks to tuck away in surround you. Mikaela was the perfect host with clear communication and forethought to all our needs. I wish we could have stayed nestled in the woods curled up by the fire for weeks!
Guest favorite

Cabin in Windsor
4.91 out of 5 average rating, 11 reviewsStone cabin in the Berkshires
JenniferRating, 5 stars2 weeks ago
This stone cabin in the woods is a great place to decompress and read a book, or write a book. The space is comfortable and cozy, with beautiful indoor and outdoor areas. Irene is a great host—she guided us through finding the place and answered questions promptly, but mostly left us alone to enjoy the beautiful surroundings. The cabin is quiet and in the woods, but within easy striking distance is excellent restaurants—shout out to the chocolate chip pancakes at M&Js in Adams.

Home in Goshen
5 out of 5 average rating, 3 reviewsGoshen Lake House
AlisonRating, 5 stars3 weeks ago
Kendra's place was pristinely clean and incredibly easy to use. It's an incredibly peaceful, quiet spot and the house is very comfortable, so we had a very relaxing stay. My son goes to school about a half hour away and we rented the place so he could have quiet time to rest and study for exams in a cozy, comfy, homey atmosphere and that is just what we got! The kitchen is well equipped and we were able to cook everything we wanted. We didn't get a chance to use the grill, but it looked great. Kendra was very responsive and communicative and our stay was totally issue-free so we didn't really need to be in close contact through our stay. The house sleeps lots of people and it could be a fun spot for a big family to have some great family-time or a group of friends to catch up. We would definitely return when we have more time to explore the pretty lake nearby and the surrounding area! Thanks Kendra!
Superhost

Apartment in Pittsfield
4.8 out of 5 average rating, 44 reviewsNewly Renovated, and Spacious great for family
KelRating, 5 stars2 months ago
Have stayed here before. Will stay again. Fits my needs and Shahs a great host
Guest favorite

Cabin in Guilford
4.96 out of 5 average rating, 73 reviewsGuilford Grove Cottage
JulieRating, 5 stars1 week ago
Joel's place was impeccably clean and free of clutter. The shower pressure was excellent. The kitchen had everything you need ro cook, and it was a treat to have milk, eggs, english muffins and coffee available for breakfast as well as tea which you can enjoy sitting out on the porch. It is a short drive to Brattleboro and the surrounding area is exquisitely beautiful.
Guest favorite

Home in Hawley
5 out of 5 average rating, 10 reviewsHawley Home w/ Deck: 4 Mi to Berkshire East Resort
GermainRating, 5 stars4 months ago
Great spot—peaceful and cozy, just the right size for three of us plus my dog. It was super close to Berkshire East for snowboarding and had plenty of hiking trails nearby. The host was friendly and communicated well. We didn’t need anything, but it was reassuring to know help was nearby if needed. Would definitely stay again!
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
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- Bash Bish Falls State Park
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- Beartown State Forest
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