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Cummington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (1,222 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
$110 nightly
The price is $123
Nov 22 - Nov 23
Total with taxes and fees
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, (2,778 reviews)
"We had an amazing stay."
United States
Luke
$117 nightly
The price is $131
Nov 22 - Nov 23
Total with taxes and fees
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, (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.
$408 nightly
The price is $431
Oct 25 - Oct 26
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

4. 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.
$446 nightly
The price is $498
Nov 16 - Nov 17
Total with taxes and fees
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.

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.
$324 nightly
The price is $361
Oct 26 - Oct 27
Total with taxes and fees
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

6. 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.
$224 nightly
The price is $250
Oct 25 - Oct 26
Total with taxes and fees
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. 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.
$174 nightly
The price is $194
Oct 25 - Oct 26
Total with taxes and fees
Rose room Victorian home queen bed private bath
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

8. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
$185 nightly
The price is $207
Nov 8 - Nov 9
Total with taxes and fees
Private room with En-suite bathroom Marigold Room
A hallway with wooden flooring, white walls, and a bed in the background.

9. Shelburne Falls on Main

Shelburne Falls on Main
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
$371 nightly
The price is $415
Oct 25 - Oct 26
Total with taxes and fees
Shelburne Falls on Main
A blue house with a porch, a wooden bench, and a door.

10. 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.
$186 nightly
The price is $208
Nov 3 - Nov 4
Total with taxes and fees
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.

11. 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.
$325 nightly
The price is $363
Nov 9 - Nov 10
Total with taxes and fees
Spacious & Cozy Ground Floor 2/3 Bed private suite
A house with a staircase leading to a porch, surrounded by snow and string lights.

12. 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
$229 nightly
The price is $255
Oct 26 - Oct 27
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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.

13. 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)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$337 nightly
The price is $376
Oct 26 - Oct 27
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern kitchen with a central island, bar stools, and a bicycle.

14. 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
$448 nightly
The price is $501
Oct 27 - Oct 28
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
A bedroom with a large bed, a nightstand with a lamp, a dresser, and a window with blinds.

15. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
$386 nightly
The price is $431
Oct 26 - Oct 27
Total with taxes and fees
A Cozy Condo Near Horse Farm + Mount Sugarloaf
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.

16. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (18 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.
$252 nightly
The price is $281
Oct 28 - Oct 29
Total with taxes and fees
Penthouse Apartment on Park Street
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

17. 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.
$651 nightly
The price is $727
Oct 25 - Oct 26
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A cozy room with two beds, large windows, and a view of a snowy landscape.

18. 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, (79 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
$251 nightly
The price is $280
Nov 3 - Nov 4
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
A hot tub with a string of lights above it, set against a dark night sky.

19. 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, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$352 nightly
The price is $393
Oct 28 - Oct 29
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A snow-covered outdoor area with a fire pit, tables, and chairs.

20. 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.
$214 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
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

River Valley Inn

River Valley Inn

8/10 Good
"Super friendly and helpful staff, convenient parking, decently sized room."
Brandon 1-night trip
Posted less than an hour ago
River Valley Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Cummington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.