Book Holiday Homes in Charlemont

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Featured Holiday Homes in Charlemont

Gorgeous 3BR 3BA Sleeps 10  Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
The price is AU$820 per night from 3 Nov to 4 Nov
AU$820
includes taxes & fees
3 Nov - 4 Nov
With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$339 per night from 11 Nov to 12 Nov
AU$339
includes taxes & fees
11 Nov - 12 Nov
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!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Located in Whitingham, this vacation home is on the waterfront, a 1-minute drive from Harriman Reservoir and 6 minutes from Jacksonville Pond.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Adams
A stay at this vacation home places you in the heart of Adams, steps from Mount Greylock State Reservation and 7 minutes by foot from East Hoosac Quaker ...
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
New Chalet mins to Mt with Hot tub

New Chalet mins to Mt with Hot tub

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.
New Chalet mins to Mt with Hot tub
Walk to Ski Lift: Spacious Condo in West Dover!

Walk to Ski Lift: Spacious Condo in West Dover!

2 out of 5
West Dover
With a stay at this vacation home in West Dover, you'll be within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Townhome Near Mount Snow Shuttle Stop!

West Dover Townhome Near Mount Snow Shuttle Stop!

2 out of 5
West Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and North Branch Deerfield River.
West Dover Townhome Near Mount Snow Shuttle Stop!
Wilmington Family Escape!  King Beds, Sleeps 13, Air hockey, Nerfgun Fun

Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun

Wilmington
The price is AU$1,097 per night from 5 Nov to 6 Nov
AU$1,097
includes taxes & fees
5 Nov - 6 Nov
With a stay at this vacation home in Wilmington, you'll be within a 10-minute walk of Buzzy Park and Pettee Memorial Library.
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
Amazing lake views & access,HotTub & sauna, quality game Rm.  190-5 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington
Located in Wilmington, this vacation home is on the waterfront, within a 5-minute walk of Deerfield River and Harriman Reservoir.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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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
396 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$1,097
Popular accommodation
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, Berkshire Village Carriage House - Super Private!!, Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, New Chalet mins to Mt with Hot tub, Walk to Ski Lift: Spacious Condo in West Dover!, West Dover Townhome Near Mount Snow Shuttle Stop!, Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Top trending hotels in Charlemont

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
Bear Creek Cabin

Bear Creek Cabin

Charlemont
The price is AU$928 per night from 3 Nov to 4 Nov
AU$928
includes taxes & fees
3 Nov - 4 Nov
Located in Charlemont, this cabin is on a river, within a 15-minute walk of Mohawk Trail State Forest and Deerfield River.
Bear Creek Cabin
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 1 Dec to 2 Dec
AU$160
includes taxes & fees
1 Dec - 2 Dec
With a stay at Red Roof Inn PLUS+ South Deerfield – Amherst in South Deerfield, you'll be within a 15-minute drive of University of Massachusetts Amherst and ...
Red Roof Inn PLUS+ South Deerfield – Amherst
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The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 10 Nov to 11 Nov
AU$176
includes taxes & fees
10 Nov - 11 Nov
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
The Covered Bridge 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.