Brattleboro Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Brattleboro

Lovely 2nd Floor Apartment

Greenfield MA

$182 nightly

$203 total

Aug 3 - Aug 4

Total with taxes and fees

Located in Greenfield, this vacation home is within a 5-minute drive of Fresenius Medical Care at Franklin Medical Center and Energy Park.

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views

Stamford VT

When you stay at this vacation home in Stamford, you'll be in the mountains, within a 15-minute drive of Green Mountain National Forest and Massachusetts Museum of Contemporary Art.

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT

With a stay at this vacation home in Jamaica (Pikes Falls), you'll be a 1-minute drive from Green Mountain National Forest and 9 minutes from Stratton Mountain Resort.

Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls MA

$319 nightly

$356 total

Aug 24 - Aug 25

Total with taxes and fees

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.

Shuttle or walk to village and lifts! Hot Tub + More!

Winhall VT

With a stay at this vacation home in Bondville, you'll be just steps from Green Mountain National Forest and 7 minutes by foot from Stratton Mountain Resort.

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Dover VT

$675 nightly

$686 total

Aug 4 - Aug 5

Total with taxes and fees

With a stay at this vacation home in West Dover, you'll be a 1-minute drive from Green Mountain National Forest and 10 minutes from Dover Free Library.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Hawley MA

Located in Charlemont, this vacation home is in the mountains, within a 15-minute drive of Hawley Bog Preserve and Swift River.

Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville VT

Located in Jacksonville, this vacation home is in the mountains, a 1-minute drive from Jacksonville Pond and 7 minutes from Harriman Reservoir.

The Jelly Mill-A Peaceful River Retreat

Guilford VT

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.

Peaceful and relaxing cottage steps from Forest Lake.

Winchester NH

Located in Winchester, this vacation home is a 4-minute drive from Winchester Speedpark and 5 minutes from New England Sweetwater Farm & Distillery.

Beautiful, private log cabin with huge, relaxing screened porch

Townshend VT

When you stay at this vacation home in Townshend, you'll be in the mountains and 12 minutes by car from West River.

Deerfield Retreat | Shuttle to Mt.Snow w/Fireplace

Dover VT

With a stay at this vacation home in West Dover, you'll be steps from Green Mountain National Forest and a 4-minute drive from Mount Snow.

Don't see what you're looking for?

See all available properties in Brattleboro

View all properties

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.