Cummington Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cummington vacation rentals

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is CA $159
CA $277 total
includes taxes & fees
Apr 28 - Apr 29
Lovely 2nd Floor Apartment

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, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is CA $125
CA $333 total
includes taxes & fees
Apr 28 - Apr 29
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

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, (75 reviews)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is CA $246
CA $385 total
includes taxes & fees
Apr 28 - Apr 29
The Creation Station is a cozy place so make yourself at home.

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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful house, immaculate and cool space! Perfect overnight after catching a show at Shea Theater."
United States
Nicole C.
The price is CA $135
CA $182 total
includes taxes & fees
Apr 28 - Apr 29
Light-filled treetop apartment close to downtown Greenfield and Highland Park

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,340 reviews)
"great stay. "
United States
John
The price is CA $118
CA $147 total
includes taxes & fees
Apr 30 - May 1
Vacation Village in the Berkshires

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, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is CA $242
CA $602 total
includes taxes & fees
Apr 28 - Apr 29
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (17 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is CA $224
CA $511 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Home in Holyoke with 3 bedrooms

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is CA $178
CA $263 total
includes taxes & fees
Apr 28 - Apr 29
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $199
CA $511 total
includes taxes & fees
Apr 28 - Apr 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is CA $219
CA $536 total
includes taxes & fees
Apr 28 - Apr 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay "
United States
Lydia T.
The price is CA $92
CA $195 total
includes taxes & fees
Apr 28 - Apr 29
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is CA $145
CA $162 total
includes taxes & fees
May 21 - May 22
Huttopia Berkshires

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (76 reviews)
"Great stay!"
United States
Shawn L.
The price is CA $166
CA $247 total
includes taxes & fees
Apr 30 - May 1
comfort, luxury, privacy

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is CA $221
CA $418 total
includes taxes & fees
Apr 28 - Apr 29
Rose wisteria 4 guests 2 bedrooms-full+queen beds

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)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is CA $144
CA $318 total
includes taxes & fees
Apr 28 - Apr 29
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $164
CA $293 total
includes taxes & fees
Apr 28 - Apr 29
Private bed with En-suite bathroom Marigold Room

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is CA $272
CA $693 total
includes taxes & fees
Apr 28 - Apr 29
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is CA $251
CA $466 total
includes taxes & fees
Apr 29 - Apr 30
Florida Mountain Log Cabin

Historic downtown apartment. Unscented products and sustainability practices.

Historic downtown apartment. Unscented products and sustainability practices.
Northampton
9.8 out of 10, Exceptional, (10 reviews)
"Quite a find in pricey Northampton. Within easy walking distance to restaurants and shops. Small but very comfortable. We didn't spend much time in the apartment, but it was perfect for what we needed."
United States
Jessica B.
The price is CA $251
CA $470 total
includes taxes & fees
Apr 28 - Apr 29
Historic downtown apartment. Unscented products and sustainability practices.

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is CA $176
CA $362 total
includes taxes & fees
Apr 30 - May 1
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cummington Hotel Reviews

Find out more about Cummington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cummington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Peace and quiet on the lake: This vacation home rental near Cummington is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 Chesterfield Gorge.

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.