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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 NZ$982 per night from 1 May to 2 May
NZ$982
includes taxes & fees
1 May - 2 May
Stay at this vacation home in Keene. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Ashuelot River and Cheshire Children's Museum are ...
Cozy Home Near Downtown, Shops, and Restaurants.
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
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
Book a stay at this ski vacation home in Stratton. Enjoy a garden, ski-in/ski-out access, and patios. Popular attractions Stratton Mountain Resort and Stratton ...
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
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
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Stay at this vacation home in Jamaica. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Hot Glass Works and Ball Mountain State ...
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
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!
 Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
The price is NZ$570 per night from 2 May to 3 May
NZ$570
includes taxes & fees
2 May - 3 May
Stay at this vacation home in Putney. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Harlow's and Next Stage Arts are located ...
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
635 Holiday Homes
Lowest Price
NZ$181
Highest Price
NZ$982
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

Top trending hotels in Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 28 Apr to 29 Apr
NZ$188
includes taxes & fees
28 Apr - 29 Apr
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Hampton Inn Brattleboro
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 4 May to 5 May
NZ$181
includes taxes & fees
4 May - 5 May
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Colonial Motel And Spa
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$309 per night from 2 May to 3 May
NZ$309
includes taxes & fees
2 May - 3 May
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Inn & Suites Brattleboro I-91
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Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$257 per night from 20 Apr to 21 Apr
NZ$257
includes taxes & fees
20 Apr - 21 Apr
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Latchis Hotel
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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.