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Compare 45 Cottages in Cummington with updated reviews, rates, and availability.

Charming historic cottage on scenic road to Mt. Greylock
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
"We spent three nights in the Stone Schoolhouse, hiking, visiting The Clarke, and enjoying a lovely evening concert at Tanglewood. Convenient location for seeing the Berkshires, unique quarters and friendly hosts. Highly recommend!"
Charming historic cottage on scenic road to Mt. Greylock
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"We had a wonderful time in Pittsfield for the Holidays. Sarah sent me a few different activities prior to our visit so I could plan some local holiday events ahead of time which was WONDERFUL! They were always responsive if there was an issue or question and the house was perfect."
Cozy Berkshire cottage with fireplace.
Massachusetts Vacation Rental w/ Deck
Terrace/patio
Massachusetts Vacation Rental w/ Deck
3.0 star property
Massachusetts Vacation Rental w/ Deck
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Property grounds
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
BBQ/picnic area
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
Living area
Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required
Picturesque Cottage with Sunroom on Ashmere Lake!
9.4 out of 10, Exceptional, (20)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Stockbridge Home: Walk to Town Beach!
Exterior
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
This living room has an oversized sectional with a large fireplace and smart TV.
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Exterior
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
Terrace/patio
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Dining
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Family-Friendly Richmond Cottage w/ Private Yard
Richmond Vacation Rental | 2BR | 2BA | 1,750 Sq Ft | Stairs Required
Family-Friendly Richmond Cottage w/ Private Yard
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great house in a beautiful location, all the amenities for kids and adults, and very clean! Highly recommended!"
Family-Friendly Richmond Cottage w/ Private Yard
Hadley Hideaway Cottage
Living area
Hadley Hideaway Cottage
10.0 out of 10, Exceptional, (3)
"My mom and I planned a trip to visit the Eric Carle Museum. The Hadley Hideaway was the perfect location. The area is very pretty, especially with the leaves changing colors. The house is very clean and had everything we needed. The hosts were very kind and responded to any requests immediately. My only issue/caution for future travelers is the house is hard to locate and Waze does not take you to the right address. "
Hadley Hideaway Cottage
Black Bear Mountain Cottage
Property grounds
Black Bear Mountain Cottage
Black Bear Mountain Cottage
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshires Cabin 2 Mi to Appalachian Trail!
Living area
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Hadley Vacation Rental 24 Mi to Springfield!
Living area
Hadley Vacation Rental 24 Mi to Springfield!
3.0 star property
Hadley Vacation Rental 24 Mi to Springfield!
Historic Huntington Home - Walk to Westfield River
Exterior
Historic Huntington Home - Walk to Westfield River
3.0 star property
Historic Huntington Home - Walk to Westfield River
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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

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1713)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is AED 620
AED 717 total
includes taxes & fees
23 Sep - 24 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is AED 537
AED 589 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
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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