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Cummington Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Cummington vacation rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,159 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is AED 292
AED 409 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Property grounds

2. 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, (39 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 AED 671
AED 1,541 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

3. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is AED 397
AED 726 total
includes taxes & fees
21 Oct - 22 Oct
Rose room Victorian home queen bed private bath
Exterior

4. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 775 total
includes taxes & fees
18 Oct - 19 Oct
Private bed with En-suite bathroom Marigold Room
Exterior detail

5. 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
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is AED 331
AED 862 total
includes taxes & fees
5 Oct - 6 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Property grounds

6. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 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 AED 992
AED 1,534 total
includes taxes & fees
29 Sep - 30 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Lobby

7. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,683 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is AED 349
AED 431 total
includes taxes & fees
30 Sep - 1 Oct
Vacation Village in the Berkshires
Coffee/tea maker, fridge, microwave, oven

8. 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, (33 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is AED 545
AED 1,204 total
includes taxes & fees
8 Oct - 9 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Interior

9. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,296 total
includes taxes & fees
29 Sep - 30 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Living area

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 AED 617
AED 1,284 total
includes taxes & fees
29 Sep - 30 Sep
Spacious & Cozy Ground Floor 2/3 Bed private suite
Iron/ironing board, WiFi, bed sheets

11. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"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 AED 771
AED 1,469 total
includes taxes & fees
29 Sep - 30 Sep
Cozy private 2 bed apartment in Shelburne Falls
Property grounds

12. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is AED 757
AED 1,251 total
includes taxes & fees
9 Oct - 10 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Interior

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is AED 511
AED 833 total
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
Desk, iron/ironing board, travel crib, WiFi

14. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is AED 661
AED 985 total
includes taxes & fees
29 Sep - 30 Sep
The Creation Station is a cozy place so make yourself at home.
Exterior

15. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is AED 248
AED 525 total
includes taxes & fees
30 Sep - 1 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,359 total
includes taxes & fees
29 Sep - 30 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor dining

17. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is AED 496
AED 1,033 total
includes taxes & fees
18 Oct - 19 Oct
Downtown | Waterfront | Walk to Shops
Smart TV, fireplace, books

18. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 1,010
AED 2,298 total
includes taxes & fees
29 Sep - 30 Sep
5BR Berkshire Home Mins To The Mountain
Living area

19. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 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 AED 533
AED 985 total
includes taxes & fees
29 Sep - 30 Sep
Penthouse Apartment on Park Street
1 bedroom, desk, iron/ironing board, WiFi

20. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is AED 419
AED 751 total
includes taxes & fees
27 Oct - 28 Oct
Balcony Room in Victorian Home private bath
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

8/10 Good
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The bathroom could use some updating. The staff were very nice."
Bridget 1-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

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 4 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 Chapel Brook.

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.