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Cummington Holiday Rentals

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Check prices for these dates

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

Our top choices for Cummington holiday 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, (1,221 reviews)
"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."
United States
ulla
The price is AU$170
includes taxes & fees
19 Nov - 20 Nov
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, (2,770 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AU$617
includes taxes & fees
25 Oct - 26 Oct
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.
The price is AU$695
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AU$500
includes taxes & fees
22 Oct - 23 Oct
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.
The price is AU$359
includes taxes & fees
25 Oct - 26 Oct
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.
The price is AU$278
includes taxes & fees
22 Oct - 23 Oct
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
The price is AU$300
includes taxes & fees
8 Nov - 9 Nov
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
The price is AU$575
includes taxes & fees
27 Oct - 28 Oct
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.
The price is AU$301
includes taxes & fees
4 Nov - 5 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Room

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.
The price is AU$510
includes taxes & fees
18 Nov - 19 Nov
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
The price is AU$366
includes taxes & fees
26 Oct - 27 Oct
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.
The price is AU$532
includes taxes & fees
29 Oct - 30 Oct
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
The price is AU$701
includes taxes & fees
27 Oct - 28 Oct
Button's Modern Luxury Walkup Downtown Northampton
A hotel room with a bed, a nightstand, a mirror, and artwork on the wall.

15. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is AU$596
includes taxes & fees
22 Oct - 23 Oct
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.
The price is AU$396
includes taxes & fees
28 Oct - 29 Oct
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.
The price is AU$1,046
includes taxes & fees
22 Oct - 23 Oct
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
The price is AU$396
includes taxes & fees
3 Nov - 4 Nov
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.
The price is AU$559
includes taxes & fees
29 Oct - 30 Oct
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.
The price is AU$340
includes taxes & fees
22 Oct - 23 Oct
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"This was our first tim"
Lorraine 2-night trip
Posted 1 hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cummington

Everything you need to know about Cummington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cummington holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cummington holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cummington holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cummington holiday rentals we have selected for you start as low as AU$144 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cummington rentals

At Expedia, we put the best Cummington holiday 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 holiday.

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 holiday rentals in Cummington?

Yes, there are holiday rentals close to the most popular sights in Cummington, or you can select 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 holiday rentals that Cummington has to offer?

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

How many holiday rentals are there in Cummington?

Expedia has 5 holiday 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 wider area, you’ll find Three Sisters Sanctuary and Berkshire East Ski Resort.

What’s a holiday rental in Cummington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cummington. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for small groups.