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Compare 201 Vacation Homes in Cummington with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 841 total
includes taxes & fees
4 Feb - 5 Feb
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (204)
"Such a cozy cabin for a perfect weekend stay with friends. Located close to multiple ski spots around the area, coming back to the cabin after to relax with hot cocoa and a fire going on. Right down the street is a shop that sells delicious sandwiches too. Owners of the property were super nice and quick to respond with any questions we had. Hoping to come back soon and check this place out during the summer time to enjoy the lake life!"
Peace and quiet on the lake

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (96)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is AED 533
AED 763 total
includes taxes & fees
11 Feb - 12 Feb
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (24)
"Great charming place to stay. Plenty of room to relax, play games, watch TV, and warm up by the wood-burning stove. Owner is very responsive and friendly and less than 10 minutes from Berkshire East. "
Charlemont Retreat on Chickley River w/ EV Charger

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (5)
"I booked the weekend for my girlfriends birthday with a couple of her friends. The game room was a massive hit as was the propane fireplace outside. We also enjoyed watching the snow fall on the frozen lake. William was very responsive to messages and calls. We enjoyed our stay immensely and are hoping to come back in the summer"
Berkshires Lakefront Retreat

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"It was just as shown in the listing. Overall was very clean and comfortable. Futon took a little figuring out to get set up and securing the shower curtain to prevent spilling water on the bathroom floor took a do-over and some clean-up, but in general was very happy with our stay and the host was very courteous and responsive."
The price is AED 474
AED 792 total
includes taxes & fees
4 Feb - 5 Feb
Lovely 2nd Floor Apartment

Amore Estate - beautiful room with many places to explore and relax in.

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Spacious Luxury Berkshire's Estate on 21 acres

Spacious Luxury Berkshire's Estate on 21 acres

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 1,183
AED 2,442 total
includes taxes & fees
4 Feb - 5 Feb
Comfortable Berkshires retreat on mtn resort, SISO

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (2)
"A great place for a family stay in downtown Amherst. "
The price is AED 874
AED 1,682 total
includes taxes & fees
3 Mar - 4 Mar
Charming 4Bds+1crib house with patio Amherst Center

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (64)
"We had a wonderful stay, thank you! "
The price is AED 1,153
AED 2,205 total
includes taxes & fees
5 Feb - 6 Feb
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Spacious 5-bedroom house steps from UMass Campus, with large backyard.

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (27)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (88)
"We have been staying here at least once a year to ski at the nearby mountains for the past several years. The home is spotless and the amenities are top notch. The house has everything you need to cook a great meal, a huge TV for a cozy movie night, comfortable king beds and the awesome, squeaky clean hot tub. The home is far enough out of town so you feel like you're getting away, while being minutes away from attractions, restaurants and stores. Thank you for sharing your home! We're already...
Hearts Desire is a furnished whole house in a small, colorful garden center.

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (19)
"Property was nice, clean, easy access to many places. Huge back yard, we had 5 adults, plenty of room for us. It was winter, so we did not utilize the screen porch or the deck so much, this would be a great place for summer visits. Overall, not a bad choice if you want a place to stay in Easthampton. "
Massachusetts Vacation Rental w/ Deck

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

9.8 out of 10, Exceptional, (10)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AED 790
AED 1,937 total
includes taxes & fees
4 Mar - 5 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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.
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Other property types in Cummington

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is AED 551
AED 641 total
includes taxes & fees
4 Feb - 5 Feb
Vacation Village in the Berkshires

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 879
AED 981 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
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.