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

Check dates for Brattleboro hotels

Vacation Rentals in Brattleboro

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.

Hot Tub

Kitchen

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT

With a stay at this vacation home in Jamaica (Pikes Falls), you'll be within a 15-minute drive of Stratton Mountain Resort and Solstice Ski Lift.

Kitchen

Washer

Lovely 2nd Floor Apartment

Greenfield MA

$194 nightly

$217 total

Jun 28 - Jun 29

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.

Kitchen

Air conditioning

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

Wilmington VT

Located in Wilmington, this vacation home is in the mountains, within a 15-minute drive of The Hermitage Golf Club and North Branch Deerfield River.

4 BR Mt Snow Okemo Ski Chalet w Amazing views!

Brattleboro VT

Located in Brattleboro, this vacation home is a 2-minute drive from Southern Vermont Natural History Museum and 6 minutes from Hogback Mountain Conservation Area.

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Whitingham VT

When you stay at this vacation home in Whitingham, you'll be on the waterfront, within a 15-minute walk of Green Mountain National Forest and Harriman Reservoir.

Hot Tub

Kitchen

Outdoor Enthusiasts Paradise in Beautiful Vermont!

Wilmington VT

Located in Wilmington, this vacation home is within a 10-minute drive of The Hermitage Golf Club and Harriman Reservoir.

Pool

Hot Tub

Heated Pool, Hot Tub, Sauna, EV Charging & more!

Winhall VT

When you stay at this vacation home in Bondville, you'll be in the mountains, just steps from Green Mountain National Forest and a 3-minute drive from Stratton Mountain Golf Course.

Spacious Corner Townhouse from Mt. Snow! Private hot tub!

Dover VT

When you stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Green Mountain National Forest and Mount Snow.

Cozy Home with Modern Upgrades in Quite Wooded Setting -Tri-St Area NH, MA, VT

Winchester NH

Located in Winchester, this vacation home is within a 5-minute drive of Ashuelot River and Winchester Speedpark.

Kitchen

Washer

Luxury with Hot Tub, Billiards & Arcades! A/C

Winhall VT

When you stay at this vacation home in Bondville, you'll be in the mountains, just steps from Green Mountain National Forest and a 2-minute drive from Stratton Mountain Golf Course.

Hot Tub

Kitchen

Family Friendly Stratton Home for All Seasons, 7 min to ski mountain

Winhall VT

When you stay at this vacation home in Bondville, you'll be in the mountains, just steps from Green Mountain National Forest and 12 minutes by foot from Winhall River.

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.