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$834 per night from 26 Nov to 27 Nov
AU$834
includes taxes & fees
26 Nov - 27 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$349 per night from 2 Dec to 3 Dec
AU$349
includes taxes & fees
2 Dec - 3 Dec
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, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
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!
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$1,092 per night from 16 Dec to 17 Dec
AU$1,092
includes taxes & fees
16 Dec - 17 Dec
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
Amherst, Perfect Location, UMass, Smith, MHC!

Amherst, Perfect Location, UMass, Smith, MHC!

Hadley
With a stay at this vacation home, you'll be centrally located in Hadley, within a 5-minute drive of University of Massachusetts Amherst and Emily Dickinson ...
Amherst, Perfect Location, UMass, Smith, MHC!
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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
389 Holiday Homes
Lowest Price
AU$161
Highest Price
AU$1,092
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!, 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, Amherst, Perfect Location, UMass, Smith, MHC!

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$930 per night from 2 Dec to 3 Dec
AU$930
includes taxes & fees
2 Dec - 3 Dec
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
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 8 Dec to 9 Dec
AU$199
includes taxes & fees
8 Dec - 9 Dec
A stay at Hotel Downstreet places you in the heart of North Adams, steps from Western Gateway Heritage State Park and 3 minutes by foot from Massachusetts Museum ...
Hotel Downstreet
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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$161 per night from 2 Dec to 3 Dec
AU$161
includes taxes & fees
2 Dec - 3 Dec
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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See all available properties in Charlemont
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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.