Book Holiday Homes in Brattleboro

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Featured Holiday Homes in Brattleboro

FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA
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.
Opens in a new windowFaLL Western Mass Getaway-Airhockey-Firepit
Amazing lake views & access,HotTub & sauna, quality game Rm.  190-5 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington VT
Located in Wilmington, this vacation home is on the waterfront, within a 5-minute walk of Deerfield River and Harriman Reservoir.
Opens in a new windowAmazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
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.
Opens in a new window 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
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Ski in Ski out Condo! Pool access

Ski in Ski out Condo! Pool access

Stratton VT
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 ...
Opens in a new windowSki in Ski out Condo! Pool access
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Opens in a new windowBeautiful Custom Built Timber Frame Home, Sleeps 11
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont VT
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Opens in a new windowLuxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA
The price is AU$617 per night from 8 Feb to 9 Feb
AU$617
8 Feb - 9 Feb
includes taxes & fees
With a stay at this vacation home in Charlemont, you'll be a 4-minute walk from Charlemont Federated Church and 5 minutes by foot from Charlemont Historical ...
Opens in a new windowRiverbend Berkshire East Basecamp - 3 bedrooms available
Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!

Jamaica VT
Located in Jamaica, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Margie's Muse Handweaving & Gallery.
Opens in a new windowSpacious Riverfront Home 7 Minutes to Stratton!
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 MA
With a stay at this vacation home in Shelburne Falls, you'll be a 1-minute walk from Deerfield River and 7 minutes by foot from Arms Cemetery.
Opens in a new windowStylish new 2 bedroom property in enchanting Shelburne Falls Village.
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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
541 Holiday Homes
Lowest Price
AU$102
Highest Price
AU$617
Popular accommodation
FaLL Western Mass Getaway-Airhockey-Firepit, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Ski in Ski out Condo! Pool access, Beautiful Custom Built Timber Frame Home, Sleeps 11, Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!, Riverbend Berkshire East Basecamp - 3 bedrooms available, Spacious Riverfront Home 7 Minutes to Stratton!, Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

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 AU$179 per night from 9 Mar to 10 Mar
AU$179
9 Mar - 10 Mar
includes taxes & fees
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Opens in a new windowHampton Inn Brattleboro
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 AU$182 per night from 9 Mar to 10 Mar
AU$182
9 Mar - 10 Mar
includes taxes & fees
When you stay at Comfort Inn & Suites Brattleboro I-91 in Brattleboro, you'll be near ski lifts, within a 10-minute walk of Connecticut River and United States ...
Opens in a new windowComfort Inn & Suites Brattleboro I-91
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is AU$102 per night from 1 Mar to 2 Mar
AU$102
1 Mar - 2 Mar
includes taxes & fees
With a stay at Econo Lodge Brattleboro South in Brattleboro, you'll be near ski lifts, just a 3-minute walk from Vermont Marketplace and 7 minutes by foot from ...
Opens in a new windowEcono Lodge Brattleboro
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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$167 per night from 7 Feb to 8 Feb
AU$167
7 Feb - 8 Feb
includes taxes & fees
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 15-minute walk of United States Navy Seabee Bridge and Brattleboro Bowl.
Opens in a new windowThe 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.