Book Holiday Homes in Charlemont

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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 NZ$391 per night from 16 Apr to 17 Apr
NZ$391
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
Stay at this vacation home in Brattleboro. Enjoy free WiFi, a garden, and patios. Popular attractions Sweet Pond State Park and Leyden State Forest are located ...
The Jelly Mill-A River Retreat
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is NZ$1,813 per night from 4 Apr to 5 Apr
NZ$1,813
includes taxes & fees
4 Apr - 5 Apr
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy a pool table, in-room washers/dryers, and an in-room coffeemaker. Popular attractions ...
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
Book a stay at this family-friendly vacation home in Amherst. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Puffers Pond South ...
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
Stay at this vacation home in Shelburne Falls. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Bald Mountain Pottery and Salmon Falls ...
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
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Mount Snow and Heavy Metal Ski ...
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
Stay at this vacation home in West Dover. Enjoy a sauna and an indoor pool. Popular attractions Mount Snow and Discovery Shuttle Ski Lift are located ...
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Book a stay at this family-friendly vacation home in Jacksonville. Enjoy a fitness center, a pool table, and cable/satellite TV service. Popular attractions ...
GAMERS HAVEN, River Wine Inn!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
Stay at this vacation home in Lanesborough. Enjoy private pools, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock ...
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
487 Holiday Homes
Lowest Price
NZ$173
Highest Price
NZ$1,813
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 NZ$1,049 per night from 16 Apr to 17 Apr
NZ$1,049
includes taxes & fees
16 Apr - 17 Apr
Stay at this cabin in Charlemont. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Rowe Town Forest and Hail to the Sunrise Statue are ...
Bear Creek Cabin
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 NZ$173 per night from 10 Apr to 11 Apr
NZ$173
includes taxes & fees
10 Apr - 11 Apr
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
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 NZ$428 per night from 6 Apr to 7 Apr
NZ$428
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
The Williams Inn
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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 NZ$248 per night from 8 Apr to 9 Apr
NZ$248
includes taxes & fees
8 Apr - 9 Apr
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
Vacation Village in the Berkshires
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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.