Book Holiday Homes in Southern Vermont

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Southern Vermont

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
When you a stay at this vacation home in Manchester Center, you'll be next to a golf course, within a 5-minute walk of Green Mountain National Forest and Battenkill ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$418 per night from 14 Apr to 15 Apr
AU$418
includes taxes & fees
14 Apr - 15 Apr
Located in Shaftsbury, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Shaftsbury Historical Society Museum.
Peaceful Stay at Birds of a Feather Farm & Spa
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
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.
The Jelly Mill-A River Retreat
Save an average of 15% on thousands of hotels when you're signed in
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
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 ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury
A stay at this vacation home places you in the heart of Shaftsbury, steps from Green Mountain National Forest and 13 minutes by foot from Robert Frost Stone ...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Located in Jamaica, this vacation home is within a 5-minute drive of West River and Green Mountain National Forest.
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
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.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
Don't see what you're looking for?
See all available properties in Southern Vermont
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.

Southern Vermont 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 Southern Vermont vacation homes are the perfect way for you to wing it.

Holiday houses in Southern Vermont 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 Southern Vermont 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 Southern Vermont adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southern Vermont 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 Southern Vermont 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.

Southern Vermont Holiday Homes essential information

Accommodation
773 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$418
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Peaceful Stay at Birds of a Feather Farm & Spa , The Jelly Mill-A River Retreat, Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, 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!

Top trending hotels in Southern Vermont

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is AU$280 per night from 2 Apr to 3 Apr
AU$280
includes taxes & fees
2 Apr - 3 Apr
When you a stay at The Equinox Golf Resort & Spa in Manchester, you'll be in the mountains, just steps from Green Mountain National Forest and Golf Club at ...
The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 28 Apr to 29 Apr
AU$238
includes taxes & fees
28 Apr - 29 Apr
A stay at Hampton Inn and Suites Manchester places you in the heart of Manchester Center, steps from Green Mountain National Forest and 8 minutes by foot from ...
Hampton Inn and Suites Manchester
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 2 Apr to 3 Apr
AU$195
includes taxes & fees
2 Apr - 3 Apr
When you stay at Mountaineer Inn in West Dover, you'll be near ski lifts, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Mountaineer Inn
Save an average of 15% on thousands of hotels when you're signed in
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$187 per night from 7 Apr to 8 Apr
AU$187
includes taxes & fees
7 Apr - 8 Apr
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
Don't see what you're looking for?
See all available properties in Southern Vermont
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.