Search Vacation Homes in Cummington

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Cummington

Spacious 5-bedroom house in charming Lee with WiFi

The price is AED 2,185
AED 3,725 total
includes taxes & fees
13 Aug - 14 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (30)
"Easy stay, good location for us. Would stay again. "
The price is AED 393
AED 702 total
includes taxes & fees
28 Jul - 29 Jul
Lovely 2nd Floor Apartment

Charming Berkshires Retreat – Minutes to Williamstown

10.0 out of 10, Exceptional, (1)
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."
Charming Berkshires Retreat – Minutes to Williamstown

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (4)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (78)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (11)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (34)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (89)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (8)
"We loved everything about this home! It fit us perfectly and we would love to rent it again!"
Historic Farmhouse Near Mountains & Colleges!

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (11)
"We had a great girls weekend e joying local trails, MassMOCA, local restaurants and this very clean, spacious house! Location is walkable to the museum and down town and we enjoyed a soak in the tub after a day of hiking in local conservation areas! "
Art House! Spacious Getaway By Mass Moca

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

9.4 out of 10, Exceptional, (14)
"Easy check in and the owner responds immediately to any questions. A really easy close drive to Berkshire East Ski Mountain. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
9.6 out of 10, Exceptional, (4)
"A great place for a family stay in downtown Amherst. "
The price is AED 787
AED 1,564 total
includes taxes & fees
29 Jul - 30 Jul
Charming 4Bds+1crib house with patio Amherst Center

Luxury Vacation Rental in the Berkshires!

10.0 out of 10, Exceptional, (14)
"Stayed here multiple times and will come back again. Great place to stay…"
Luxury Vacation Rental in the Berkshires!

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AED 744
AED 1,651 total
includes taxes & fees
21 Jul - 22 Jul
North Getaway Cottage

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (27)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (1)
"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "
The price is AED 551
AED 1,251 total
includes taxes & fees
31 Jul - 1 Aug
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Charming 3-bedroom farmhouse in Lenox

Charming 3-bedroom farmhouse in Lenox

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in