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Featured Holiday Homes in Charlemont

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$381 per night from 8 Apr to 9 Apr
AU$381
includes taxes & fees
8 Apr - 9 Apr
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is AU$1,733 per night from 11 Apr to 12 Apr
AU$1,733
includes taxes & fees
11 Apr - 12 Apr
With a stay at this vacation home in Pittsfield, you'll be on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
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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
With a stay at this vacation home, you'll be centrally located in Amherst, a 4-minute drive from University of Massachusetts Amherst and 6 minutes from Amherst ...
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be in the mountains, within a 15-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Mountain Blossom Retreat by Evergreen Home
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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.

Charlemont 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 Charlemont vacation homes are the perfect way for you to wing it.

Holiday houses in Charlemont 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 Charlemont 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 Charlemont adventures, obvs.

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

Charlemont Holiday Homes essential information

Accommodation
469 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$1,733
Popular accommodation
Berkshire Village Carriage House - Super Private!!, The Jelly Mill-A River Retreat, Hancock Village Inn at Jiminy Peak, kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Mountain Blossom Retreat by Evergreen Home

Top trending hotels in Charlemont

Bear Creek Cabin

Bear Creek Cabin

Charlemont
The price is AU$1,001 per night from 15 Apr to 16 Apr
AU$1,001
includes taxes & fees
15 Apr - 16 Apr
Located in Charlemont, this cabin is on a river, within a 5-minute drive of Deerfield River and Rowe Town Forest.
Bear Creek Cabin
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Hawley
Located in Charlemont, this vacation home is in the mountains, within a 15-minute drive of Hawley Bog Preserve and Swift River.
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 14 Apr to 15 Apr
AU$163
includes taxes & fees
14 Apr - 15 Apr
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
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The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$448 per night from 9 Apr to 10 Apr
AU$448
includes taxes & fees
9 Apr - 10 Apr
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
The Williams Inn
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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.