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Featured Holiday Homes in Brattleboro

Cozy Home Near Downtown, Shops, and Restaurants.

Cozy Home Near Downtown, Shops, and Restaurants.

2 out of 5
Keene
The price is AU$909 per night from 21 May to 22 May
AU$909
includes taxes & fees
21 May - 22 May
Located in Keene, this vacation home is within a 15-minute walk of Ashuelot River and Cheshire Children's Museum.
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
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1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Located in Jamaica, this vacation home is in the mountains, within a 5-minute drive of West River and Green Mountain National Forest.
Potter's Place | House in Jamaica with mountain views
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
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
 Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
The price is AU$532 per night from 9 May to 10 May
AU$532
includes taxes & fees
9 May - 10 May
Located in Putney, this vacation home is on a lake, within a 5-minute drive of Harlow's and Next Stage Arts.
Family Friendly Hilltop House In Putney Vermont
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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.

Brattleboro 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 Brattleboro vacation homes are the perfect way for you to wing it.

Holiday houses in Brattleboro 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 Brattleboro 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 Brattleboro adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Brattleboro 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 Brattleboro 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.

Brattleboro Holiday Homes essential information

Accommodation
609 Holiday Homes
Lowest Price
AU$532
Highest Price
AU$909
Popular accommodation
Cozy Home Near Downtown, Shops, and Restaurants., The Jelly Mill-A River Retreat, Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Potter's Place | House in Jamaica with mountain views, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Family Friendly Hilltop House In Putney Vermont

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^Subject to availability and chosen travel dates.