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$381 per night from 25 Apr to 26 Apr
NZ$381
includes taxes & fees
25 Apr - 26 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$1,739 per night from 28 Apr to 29 Apr
NZ$1,739
includes taxes & fees
28 Apr - 29 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$176
Highest Price
NZ$1,739
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$1,004 per night from 25 Apr to 26 Apr
NZ$1,004
includes taxes & fees
25 Apr - 26 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
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
Stay at this vacation home in Charlemont. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Hawley Bog Preserve and Berkshire East ...
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
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 NZ$176 per night from 28 Apr to 29 Apr
NZ$176
includes taxes & fees
28 Apr - 29 Apr
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Red Roof Inn PLUS+ South Deerfield – Amherst
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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 NZ$193 per night from 28 Apr to 29 Apr
NZ$193
includes taxes & fees
28 Apr - 29 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
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.