
Holiday rentals in Cummington
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Top-rated holiday rentals in Cummington
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Other great holiday rentals in Cummington
Guest favourite

Cabin in Williamsburg
4.94 out of 5 average rating, 35 reviewsRetreat in the Woods
MeghanRating, 5 stars2 days ago
Maya’s place was the perfect spot for a peaceful, serene getaway. The home is private, safe, easy to access thanks to clear check-in instructions, and was spotless upon our arrival. It’s clear that a lot of care and attention go into making this cabin comfortable and welcoming for guests. There were many thoughtful, homey touches throughout—from the bookshelf stocked with great reading material to the cozy string lights in the living room and the beautiful three-season porch. We stayed during one of the hottest weekends of the season so far, and even without air conditioning, the cabin stayed cool and comfortable. Maya kindly provided fans and left all of the windows open for us in advance of our arrival. We left feeling grounded and refreshed, having enjoyed sightings of butterflies and other wildlife as we came and went. Though we only stayed for the weekend, we would’ve happily lingered longer to soak in the tranquility and natural beauty. Highly recommend!

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 favourite

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 favourite

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 stars4 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!
Guest favourite

Cabin in Guilford
4.96 out of 5 average rating, 75 reviewsGuilford Grove Cottage
LindaRating, 5 stars1 day ago
What a wonderful little cabin off the beaten path. Very clean & cozy.. we came up for the Green River Festival in Greenfield, MA, which was about 25 mins away & it was no problem finding this place.. beautiful scenery surrounds the land from flowers, trees, birds etc.. the bed was very comfortable, Joel provided fresh eggs and milk from the local farm nearby. Just a very nice atmosphere and we hope to be back soon..
Guest favourite

Home in Ashfield
4.98 out of 5 average rating, 88 reviewsMagical, Rural Getaway in the Berkshires
DavidRating, 5 stars2 weeks ago
This is a truly peaceful and comfortable home in a beautiful spot. The house is well appointed and everything is clearly explained. The nights are dark and super quiet.

Farm stay in Adams
5 out of 5 average rating, 4 reviewsBerkshires/Pet Friendly farm stay w/mountain views
SarahRating, 5 stars1 week ago
We had a great week full of hiking at Mt. Greylock and walking the local rail trail with our pups! Jessica’s place was a perfect touch down for everything we wanted to do. The camper felt private and cozy, a perfect place to relax and view beautiful scenery from the field. Getting to see the horses was a plus and our dogs loved hanging in the back yard. The camper was clean, comfortable and Jessica was very accommodating, making sure we had everything we needed! This is a place we would definitely come back to if we are in Adams 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
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
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- The Shattuck Golf Club
- Mohawk Mountain Ski Area
- Beartown State Forest
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- Hartford Golf Club
- Hancock Shaker Village
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- Naumkeag
- Hildene, The Lincoln Family Home