Book Holiday Homes in Cummington

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Featured Holiday Homes in Cummington

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Easthampton
Located in Easthampton, this vacation home is in a rural location, within a 10-minute drive of Conant Park and Smith College.
Opens in a new windowOld World Charm, Modern Conveniences - 3 BR private home in quiet setting
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
The price is AU$311 per night from 29 Sept to 30 Sept
AU$311
29 Sept - 30 Sept
includes taxes & fees
Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.
Opens in a new windowLovely 2nd Floor Apartment
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Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Pownal
With a stay at this vacation home in Pownal, you'll be steps from Green Mountain National Forest and a 3-minute drive from Mountain Meadow Preserve.
Opens in a new windowBright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
The price is AU$1,269 per night from 21 Oct to 22 Oct
AU$1,269
21 Oct - 22 Oct
includes taxes & fees
With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowSpacious 5-bedroom house in charming Lee with WiFi
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Wyndhurst Golf & Club.
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

Cummington
With a stay at this vacation home in Cummington, you'll be on the waterfront, and 8.1 mi (13 km) from Swift River and 8.3 mi (13.3 km) from Westfield River.
Opens in a new window3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Opens in a new windowContemporary Berkshire Home with Views of Taconic Golf Course
Wildlife Lakeside Cottage
beautiful views, amazing wildlife, great location

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be on a lake, within a 15-minute drive of Jiminy Peak Mountain Resort and St Mary's of the Assumption ...
Opens in a new windowWildlife Lakeside Cottage beautiful views, amazing wildlife, great location
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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.

Cummington Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cummington vacation homes are the perfect way for you to wing it.

Holiday houses in Cummington let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cummington in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cummington adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cummington with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cummington vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cummington Holiday Homes essential information

Accommodation
244 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$1,269
Popular accommodation
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Old World Charm, Modern Conveniences - 3 BR private home in quiet setting, Lovely 2nd Floor Apartment, Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., 3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest, Contemporary Berkshire Home with Views of Taconic Golf Course, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Top trending hotels in Cummington

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 20 Oct to 21 Oct
AU$186
20 Oct - 21 Oct
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 26 Oct to 27 Oct
AU$247
26 Oct - 27 Oct
includes taxes & fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 28 Sept to 29 Sept
AU$193
28 Sept - 29 Sept
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Opens in a new windowBerkshire Mountain Lodge
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D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 23 Oct to 24 Oct
AU$195
23 Oct - 24 Oct
includes taxes & fees
With a stay at D. Hotel Suites & Spa in Holyoke, you'll be 4.6 mi (7.4 km) from Smith College and 10.4 mi (16.7 km) from University of Massachusetts ...
Opens in a new windowD. Hotel Suites & Spa
Don't see what you're looking for?
See all available properties in Cummington
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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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^Subject to availability and chosen travel dates.