Book Holiday Homes in Southern Vermont

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Featured Holiday Homes in Southern Vermont

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
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$416 per night from 24 Aug to 25 Aug
AU$416
24 Aug - 25 Aug
includes taxes & fees
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
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

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

Winhall
The price is AU$1,142 per night from 26 Aug to 27 Aug
AU$1,142
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
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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!
Mountain Sanctuary Dome Rustic Solitude 5BR

Mountain Sanctuary Dome Rustic Solitude 5BR

Pownal
Located in Bennington, this vacation home is within a 15-minute drive of Green Mountain National Forest and Taconic Ridge State Forest.
Mountain Sanctuary Dome Rustic Solitude 5BR
The Mountain Escape!

The Mountain Escape!

Jamaica
The price is AU$881 per night from 1 Sept to 2 Sept
AU$881
1 Sept - 2 Sept
includes taxes & fees
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!
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Manchester
With a stay at this vacation home in Manchester, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 12 minutes by foot ...
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Room for the whole family 8 minutes to Manchester

Room for the whole family 8 minutes to Manchester

Sunderland
With a stay at this vacation home in Arlington, you'll be steps from Green Mountain National Forest and a 2-minute drive from Battenkill River.
Room for the whole family 8 minutes to Manchester
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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.

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$205
Highest Price
AU$1,142
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, Peaceful Stay at Birds of a Feather Farm & Spa , Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym, Timeless Red Sox Retreat w/ Scenic Mountain Views!, Mountain Sanctuary Dome Rustic Solitude 5BR , The Mountain Escape!, Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, Beautiful Custom Built Timber Frame Home, Sleeps 11, Room for the whole family 8 minutes to Manchester

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$323 per night from 26 Aug to 27 Aug
AU$323
26 Aug - 27 Aug
includes taxes & fees
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
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
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
The price is AU$388 per night from 20 Aug to 21 Aug
AU$388
20 Aug - 21 Aug
includes taxes & fees
With a stay at Kimpton Taconic Hotel by IHG in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and 5 minutes ...
Kimpton Taconic Hotel by IHG
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is AU$205 per night from 4 Sept to 5 Sept
AU$205
4 Sept - 5 Sept
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
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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.