Book Holiday Homes in Charlemont
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Featured Holiday Homes in Charlemont

Charming Berkshires Retreat – Minutes to Williamstown

The Jelly Mill-A Peaceful River Retreat

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Contemporary Berkshire Home with Views of Taconic Golf Course

Private Family Estate for any Season

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

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

Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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 | 495 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Charming Berkshires Retreat – Minutes to Williamstown, The Jelly Mill-A Peaceful River Retreat, Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, Contemporary Berkshire Home with Views of Taconic Golf Course, Private Family Estate for any Season, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort.., Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, Lake Front Home in Heart of the Berkshires Near Jiminy Peak |
More accommodations in Charlemont
Top trending hotels in Charlemont

Bear Creek Cabin

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

Red Roof Inn PLUS+ South Deerfield – Amherst

The Yankee, Trademark Collection by Wyndham
More ways to explore Charlemont
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^Subject to availability and chosen travel dates.