Holiday Homes in Cummington

Start date: Check-in selected.
End date: Check-out
    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

In two weeks
In two months
In three months
In four months

Featured Holiday Homes in Cummington

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (21)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Stunning 3BR Riverfront Log Home with Soaring Glass Wall & Private Forest

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is NZ$343
includes taxes & fees
8 Sept - 9 Sept
Lovely 2nd Floor Apartment

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (71)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

10.0 out of 10, Exceptional, (23)
"The property was beautiful! The kids enjoyed fishing in the pond with their grandpa. The hosts were nice enough to let us have a small impromptu family cookout and were very helpful when we accidentally locked ourselves out. It was a great stay!"
Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge

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

10.0 out of 10, Exceptional, (93)
"This was our third time at this property. We still love it and look forward to returning again."
Hearts Desire is a furnished whole house in a small, colorful garden center.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is NZ$1,886
includes taxes & fees
8 Sept - 9 Sept
Hancock Village Inn at Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,047
includes taxes & fees
14 Sept - 15 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is NZ$806
includes taxes & fees
8 Sept - 9 Sept
Comfortable Berkshires retreat on mtn resort, SISO

Peace and quiet on the lake

9.6 out of 10, Exceptional, (219)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (6)
Contemporary Berkshire Home with Views of Taconic Golf Course

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

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

9.6 out of 10, Exceptional, (71)
"We love this comfortable cottage and quiet location, perfect for a relaxing vacation spent bird watching, biking the nearby rail trail, and hiking with our dog. This was our fourth time staying here-- impressed with the beautiful updates to the master bedroom, now a suite with its own bathroom! We'll be coming back again!"
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Hadley Hideaway Cottage

10.0 out of 10, Exceptional, (10)
"Great location for access to Northampton and also nearby hiking!"
Hadley Hideaway Cottage

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

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

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

10.0 out of 10, Exceptional, (5)
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

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

Top Cummington Hotel Reviews

Find out more about Cummington

Find out more about Cummington

Cummington Holiday Homes information

Number of reviews
Accommodation
275 Holiday Homes
Lowest Price
NZ$343
Highest Price
NZ$1,886