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Cummington Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Cummington vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is ￥13,678
￥18,810 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,745 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is ￥12,701
￥15,921 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
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, (43 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 ￥42,682
￥67,170 total
includes taxes & fees
Oct 25 - Oct 26
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

4. 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 ￥15,178
￥29,138 total
includes taxes & fees
Nov 4 - Nov 5
2 Twin beds on 1st floor with En-suite bathroom.
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

5. 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, (34 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 ￥23,475
￥56,770 total
includes taxes & fees
Oct 19 - Oct 20
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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 ￥35,568
￥78,752 total
includes taxes & fees
Nov 8 - Nov 9
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥18,970
￥33,902 total
includes taxes & fees
Oct 19 - Oct 20
Private bed with En-suite bathroom Marigold Room
A blue house with a porch, a wooden bench, and a door.

8. 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 ￥13,374
￥36,835 total
includes taxes & fees
Oct 27 - Oct 28
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

9. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is ￥19,776
￥33,744 total
includes taxes & fees
Oct 18 - Oct 19
Lovely 2nd Floor Apartment
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.

10. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.8 out of 10, Exceptional, (17 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 ￥22,922
￥44,497 total
includes taxes & fees
Oct 29 - Oct 30
Penthouse Apartment on Park Street
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. 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 ￥17,073
￥31,607 total
includes taxes & fees
Oct 20 - Oct 21
Rose room Victorian home queen bed private bath
A hallway with wooden flooring, white walls, and a bed in the background.

12. 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 ￥33,197
￥67,630 total
includes taxes & fees
Oct 19 - Oct 20
Cozy private 2 bed apartment in Shelburne Falls
A kitchen with wooden cabinets, a stainless steel dishwasher, and a dining table with benches.

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

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is ￥19,128
￥48,736 total
includes taxes & fees
Oct 19 - Oct 20
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A living room with a beige sofa, a patterned rug, and a wooden floor.

14. 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 ￥26,561
￥58,456 total
includes taxes & fees
Nov 3 - Nov 4
Spacious & Cozy Ground Floor 2/3 Bed private suite
Room

15. Queen Bedroom in Victorian Home private bath.

Queen Bedroom in Victorian Home private bath.
Shelburne Falls
The price is ￥18,021
￥33,020 total
includes taxes & fees
Nov 3 - Nov 4
Queen Bedroom in Victorian Home 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.

16. 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 ￥23,048
￥59,294 total
includes taxes & fees
Oct 28 - Oct 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 ￥11,698
￥50,323 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A modern kitchen with a central island, bar stools, and a bicycle.

18. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ￥38,584
￥79,119 total
includes taxes & fees
Oct 26 - Oct 27
Button's Modern Luxury Walkup Downtown Northampton
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

19. 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 ￥51,344
￥114,739 total
includes taxes & fees
Oct 18 - Oct 19
5BR Berkshire Home Mins To The Mountain
A wooden bookshelf with multiple shelves filled with books and a small toy car.

20. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (13 reviews)
"Nice place"
United States
Tom
The price is ￥32,011
￥40,347 total
includes taxes & fees
Oct 26 - Oct 27
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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

Hotel On North

Hotel On North

10/10 Excellent
"The hotel is charming in the heart of Pittsfield. The rooms were large and clean. It’s a great boutique hotel with 35 rooms. There is a restaurant attached to the hotel that had great food and drinks! Will definitely be back."
Tanya 2-night trip
Posted 1 day ago
Hotel On North

Find out more about Cummington

Search for holiday rentals in Cummington on Expedia! You can easily find your home rentals, villas, holiday apartments in Cummington using one of the methods below:

  • View our selection of featured holiday rentals in Cummington
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  • Enter your travel dates to view the best deals on holiday rentals in Cummington while they last

Look no further and take a look at our great range of rental properties in Cummington!

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.