Cummington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cummington vacation rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,258 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $108
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

2. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is CA $129
CA $241 total
includes taxes & fees
Nov 8 - Nov 9
2 Twin beds on 1st floor with En-suite bathroom.
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

3. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is CA $346
CA $558 total
includes taxes & fees
Dec 6 - Dec 7
Charming, updated 3 bedroom farmhouse farm stay.
Indoor pool

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,833 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $113
CA $141 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $161
CA $277 total
includes taxes & fees
Nov 8 - Nov 9
Private room with En-suite bathroom Marigold Room
A hot tub with a wooden deck and chairs, a white building with windows, and a clear sky.

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is CA $251
CA $592 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

7. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is CA $158
CA $422 total
includes taxes & fees
Nov 10 - Nov 11
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

8. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is CA $73
CA $387 total
includes taxes & fees
Nov 9 - Nov 10
Real Estate: Therapy - Lake, Laundry, Love it
A blue house with a porch, a wooden bench, and a door.

9. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is CA $124
CA $320 total
includes taxes & fees
Nov 9 - Nov 10
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A living room with a beige sofa, a patterned rug, and a wooden floor.

10. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is CA $226
CA $487 total
includes taxes & fees
Nov 8 - Nov 9
Spacious & Cozy Ground Floor 2/3 Bed private suite
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is CA $153
CA $267 total
includes taxes & fees
Nov 8 - Nov 9
Balcony Room in Victorian Home private bath
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

12. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is CA $203
CA $374 total
includes taxes & fees
Nov 8 - Nov 9
Penthouse Apartment on Park Street
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is CA $214
CA $332 total
includes taxes & fees
Nov 8 - Nov 9
Lovely 2nd Floor Apartment
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

14. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is CA $163
CA $399 total
includes taxes & fees
Nov 9 - Nov 10
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A hallway with wooden flooring, white walls, and a bed in the background.

15. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is CA $282
CA $555 total
includes taxes & fees
Nov 8 - Nov 9
Shelburne Falls on Main
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

16. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is CA $145
CA $258 total
includes taxes & fees
Nov 8 - Nov 9
Rose room Victorian home queen bed private bath
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is CA $204
CA $504 total
includes taxes & fees
Nov 9 - Nov 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is CA $120
CA $273 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A modern two-story house with large windows and a balcony.

19. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is CA $701
CA $850 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Valley View Post & Beam Villa!
A hot tub with a string of lights above it, set against a dark night sky.

20. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $225
CA $528 total
includes taxes & fees
Nov 9 - Nov 10
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
The Ellery

The Ellery

The Ellery
Northampton

10/10 Excellent

We stayed 5 days in the ground floor coach house room which was a lovely, large room with a sitting and dinning area as well as a private patio area. The room was lovely, AC worked great on an extremely hot week and the breakfast, all days snacks and common area were great as well. The staff was helpful with tips about things to do in the area. We had a great visit.
Canada
Graham
Reviewed July 5, 2026
The Ellery

Find out more about Cummington

Everything you need to know about Cummington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cummington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cummington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cummington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cummington. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cummington vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cummington vacation rentals we have selected for you start as low as CA $72 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cummington rentals

At Expedia, we put the best Cummington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cummington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cummington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cummington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Cummington?

Yes, we give you a choice of vacation rentals close to popular sights in Cummington, or you can go with a more secluded option if you're looking for a relaxing stay. Cummington is known for its shopping and restaurants.

What are some of the best vacation rentals that Cummington has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental near Cummington is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Cummington?

Expedia has 5 vacation rentals for your stay in Cummington.

What’s there to see and do in Cummington?

Swift River and Westfield River are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Three Sisters Sanctuary and Berkshire East Ski Resort.

What’s a vacation rental in Cummington like?

A vacation rental is a private property where you can stay for a long or short time in Cummington. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for families.