Book Holiday Homes in Chelsea
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Featured Holiday Homes in Chelsea

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Dog-friendly home with panoramic mountain views, grill, deck, & pool table

4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake

Storybook House on Wrights Mountain

Spacious country home, beautiful sunsets, 40 acres

Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome.

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush
Chelsea 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 Chelsea vacation homes are the perfect way for you to wing it.
Holiday houses in Chelsea 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 Chelsea 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 Chelsea adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chelsea 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 Chelsea 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.
Chelsea Holiday Homes essential information
Accommodation | 217 Holiday Homes |
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Popular accommodation | Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Dog-friendly home with panoramic mountain views, grill, deck, & pool table, 4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake, Storybook House on Wrights Mountain, Spacious country home, beautiful sunsets, 40 acres, Rural Vermont with internet and Smart TV, cell phone works, Dogs welcome., Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak, Charming and spacious 5BR located in the heart of Waitsfield. Close to amenities, 5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush |
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Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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^Subject to availability and chosen travel dates.