Cummington Vacation Rentals

Q: 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.

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Dates

November 2026

December 2026

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Our top choices for Cummington vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Charline

$106 nightly

Dec 7 - Dec 8

Total with taxes and fees

A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

2. 2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls

$153 nightly

Nov 8 - Nov 9

Total with taxes and fees

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.

Williamsburg

Nancy M.

$375 nightly

Dec 6 - Dec 7

Total with taxes and fees

4. Vacation Village in the Berkshires

Williamstown

Marcos

$122 nightly

Dec 6 - Dec 7

Total with taxes and fees

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

5. Private room with En-suite bathroom Marigold Room

Shelburne Falls

$177 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hot tub with a wooden deck and chairs, a white building with windows, and a clear sky.

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

Hinsdale

Kyle R.

$378 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

7. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

$270 nightly

Nov 10 - Nov 11

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

$247 nightly

Nov 9 - Nov 10

Total with taxes and fees

A blue house with a porch, a wooden bench, and a door.

9. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Greenfield

JAMES S.

$203 nightly

Nov 9 - Nov 10

Total with taxes and fees

A living room with a beige sofa, a patterned rug, and a wooden floor.

10. Spacious & Cozy Ground Floor 2/3 Bed private suite

Shelburne Falls

Russ D.

$308 nightly

Nov 8 - Nov 9

Total with taxes and fees

11. Balcony Room in Victorian Home private bath

Shelburne Falls

$172 nightly

Nov 8 - Nov 9

Total with taxes and fees

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.

12. Penthouse Apartment on Park Street

Adams

Margaret C.

$239 nightly

Nov 7 - Nov 8

Total with taxes and fees

A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

13. Lovely 2nd Floor Apartment

Greenfield

heather

$213 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

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

Sunderland

$249 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hallway with wooden flooring, white walls, and a bed in the background.

15. Shelburne Falls on Main

Shelburne Falls

maureen

$354 nightly

Nov 8 - Nov 9

Total with taxes and fees

16. Rose room Victorian home queen bed private bath

Shelburne Falls

Mikaela M.

$165 nightly

Nov 8 - Nov 9

Total with taxes and fees

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.

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Brian C.

$320 nightly

Nov 8 - Nov 9

Total with taxes and fees

A kitchen with a Keurig coffee maker, storage jars, and a knife block.

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

North Adams

Ruthie K.

$185 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern two-story house with large windows and a balcony.

19. Cozy Valley View Post & Beam Villa!

Whately

Andrea M.

$542 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

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

Sherwood Forest

Frank M.

$335 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Cummington Hotel Reviews

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

The Ellery

Northampton

10/10 Excellent

Marilyn

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

10/10 Excellent

Lauren

An outdoor patio area with a circular fire pit surrounded by wicker chairs and tables.

TownePlace Suites by Marriott Hadley Amherst

Hadley

10/10 Excellent

Karen

A hotel lobby with a bar area, dining tables, and comfortable seating.

Hampton Inn Hadley-Amherst Area

Hadley

10/10 Excellent

Reina

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

Hampton Inn & Suites Greenfield

Greenfield

10/10 Excellent

Carol

A room with a bed, a sofa, a coffee table, and a television.

Black Walnut Inn

North Amherst

10/10 Excellent

Sofia

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A two-story house with a porch, a balcony, and a chimney.

Blooming Inn

Shelburne Falls

10/10 Excellent

Philip M

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

Courtyard by Marriott Hadley Amherst

Hadley

10/10 Excellent

This is a great hotel for a short stay. Everything was top-notch except the 4 1/2' deep, 3-stroke pool could hardly be called a swimming pool. I should have read between the lines when "pool" was listed as a "family amenity". There is no restaurant other than a small bar that serves a la carte breakfast items in the morning. The 6-stool bar was not especially well-stocked but fine for a quick nightcap. The breakfast buffet was excellent and well-priced. The building is designed with an open...

Scubamouse

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 $118 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.

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.

Cummington Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Cummington vacation rentals

1. Berkshire Mountain Lodge

2. 2 Twin beds on 1st floor with En-suite bathroom.

3. Charming, updated 3 bedroom farmhouse farm stay.

4. Vacation Village in the Berkshires

5. Private room with En-suite bathroom Marigold Room

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

7. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

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

9. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

10. Spacious & Cozy Ground Floor 2/3 Bed private suite

11. Balcony Room in Victorian Home private bath

12. Penthouse Apartment on Park Street

13. Lovely 2nd Floor Apartment

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

15. Shelburne Falls on Main

16. Rose room Victorian home queen bed private bath

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

18. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

19. Cozy Valley View Post & Beam Villa!

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

Find vacation rentals that suit your style

Top Cummington Hotel Reviews

The Ellery

10/10 Excellent

Find out more about Cummington

Everything you need to know about Cummington vacation rentals

Cummington vacation rentals: An excellent choice for every season

How to find incredible deals on Cummington rentals

Frequently Asked Questions

Can I find vacation rentals in Cummington?

What are some of the best vacation rentals that Cummington has to offer?

How many vacation rentals are there in Cummington?

What’s there to see and do in Cummington?

What’s a vacation rental in Cummington like?

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