Cummington Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Cummington Vacation Homes

Lovely 2nd Floor Apartment
Relax in a serene space with a comfortable armchair, console table, and lush greenery.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is CA $160
CA $277 total
includes taxes & fees
Aug 13 - Aug 14
Lovely 2nd Floor Apartment
Contemporary Berkshire Home with Views of Taconic Golf Course
Relax in this spacious living room with a high ceiling, featuring a sofa, armchair, and coffee table.

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Step out onto the porch and enjoy the fresh air from the comfort of two chairs and a small table.

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

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (3)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Stunning two-story home with a gabled roof and inviting front porch.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (12)
"The place was very comfortable and in a great location. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Enjoy meals and games in this kitchen with a central island and pool table.

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

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is CA $234
CA $512 total
includes taxes & fees
Aug 12 - Aug 13
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Enjoy cooking in this well-equipped kitchen with a fireplace, large island, and flat-screen TV.

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

10.0 out of 10, Exceptional, (46)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Enjoy a functional kitchen with a central island, perfect for meal prep and dining.

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

10.0 out of 10, Exceptional, (81)
"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
Quiet Cabin On Over 12 Acres Of Woods!
Cozy living space with a central island kitchen, spiral staircase, and comfortable seating area.

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (12)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!
Art House! Spacious Getaway By Mass Moca
Meetings and gatherings take place in this elegantly designed room with a long table and comfortable seating.

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
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Relax in this serene space with a comfortable chair and a staircase leading to an upper level.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (45)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Relax in a serene outdoor space with a shaded table and chairs surrounded by lush greenery.

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
StrautmanHaus - All-Season Chalet at Berkshire East
Enjoy meals in this kitchen with an oven, microwave, and stove, adjacent to a dining area with a large window offering a view of the outdoors.

StrautmanHaus - All-Season Chalet at Berkshire East

9.8 out of 10, Exceptional, (13)
"The house was definitely nice and we enjoyed our stay. I didn’t give it 5 stars because the two downstairs bedrooms had a strong musty smell."
StrautmanHaus - All-Season Chalet at Berkshire East
Cabin Retreat in the Berkshire Woods
Cozy living area with a central staircase, comfortable seating, and dining space.

Cabin Retreat in the Berkshire Woods

Cabin Retreat in the Berkshire Woods
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Situated on a lush lawn, this charming house features a wrap-around porch and a prominent gable roof.

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..
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Relax in a spacious living area with a high ceiling and comfortable seating, perfect for socializing and unwinding.

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (94)
"Exactly what you want in a ski house!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Charming 3-bedroom farmhouse in Lenox
Relax on the outdoor deck with Adirondack chairs, perfect for a quiet moment or al fresco dining.

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox
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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Top Cummington Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."
Susan 6-night trip
Posted 1 day ago
Berkshire Mountain Lodge