Book Holiday Homes in Brattleboro

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Featured Holiday Homes in Brattleboro

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
The price is AU$311 per night from 21 Aug to 22 Aug
AU$311
21 Aug - 22 Aug
includes taxes & fees
Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.
Lovely 2nd Floor Apartment
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Winhall
Located in Bondville, this vacation home is on the waterfront, within a 15-minute drive of Green Mountain National Forest and Winhall River.
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
The price is AU$766 per night from 17 Aug to 18 Aug
AU$766
17 Aug - 18 Aug
includes taxes & fees
With a stay at this vacation home in Keene, you'll be within a 10-minute walk of Cheshire Rail Trail and Historic Main Street.
Downtown Hot Tub Escape
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Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2 out of 5
Shelburne Falls
With a stay at this apartment in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall
The price is AU$1,145 per night from 26 Aug to 27 Aug
AU$1,145
26 Aug - 27 Aug
includes taxes & fees
With a stay at this vacation home in Bondville, you'll be in the mountains, within a 15-minute drive of Stratton Mountain Resort and Green Mountain National ...
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Timeless Red Sox Retreat w/ Scenic Mountain Views!

Timeless Red Sox Retreat w/ Scenic Mountain Views!

Putney
Located in Putney, this vacation home is a 4-minute drive from Connecticut River and 6 minutes from Butterfield Library.
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Story Book Lake Front Chateau with Private Beach!

Story Book Lake Front Chateau with Private Beach!

Winchester
Located in Winchester, this vacation home is a 5-minute drive from Ashuelot River and 6 minutes from Winchester Speedpark.
Story Book Lake Front Chateau with Private Beach!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Colrain
The price is AU$576 per night from 14 Aug to 15 Aug
AU$576
14 Aug - 15 Aug
includes taxes & fees
Located in Colrain, this vacation home is within a 5-minute drive of Arthur A. Smith Covered Bridge and G. William Pitt House and Collection.
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
The Mountain Escape!

The Mountain Escape!

Jamaica
With a stay at this vacation home, you'll be centrally located in Bondville, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National ...
The Mountain Escape!
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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
637 Holiday Homes
Lowest Price
AU$214
Highest Price
AU$1,145
Popular accommodation
Lovely 2nd Floor Apartment, Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, Downtown Hot Tub Escape, Stylish new 2 bedroom property in enchanting Shelburne Falls Village., Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym, Timeless Red Sox Retreat w/ Scenic Mountain Views!, Story Book Lake Front Chateau with Private Beach!, Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls, The Mountain Escape!

Top trending hotels in 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 AU$236 per night from 14 Aug to 15 Aug
AU$236
14 Aug - 15 Aug
includes taxes & fees
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is AU$214 per night from 24 Aug to 25 Aug
AU$214
24 Aug - 25 Aug
includes taxes & fees
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
The price is AU$230 per night from 9 Sept to 10 Sept
AU$230
9 Sept - 10 Sept
includes taxes & fees
When you stay at Latchis Hotel in Brattleboro, you'll be near ski lifts, just steps from Latchis Theatre and 5 minutes by foot from The Stone Church.
Latchis Hotel
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The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$232 per night from 13 Sept to 14 Sept
AU$232
13 Sept - 14 Sept
includes taxes & fees
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
The Covered Bridge Inn
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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.