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
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful 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 Peaceful River Retreat
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

Winhall
With a stay at this vacation home in Bondville, you'll be within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
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By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Winhall
With a stay at this vacation home in Bondville, you'll be on the waterfront, just steps from Green Mountain National Forest and a 4-minute drive from Bromley ...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

Sandgate
Located in Arlington, this vacation home is on a river, within a 15-minute drive of Green Mountain National Forest and Battenkill River.
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Manchester,  Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Sunderland
With a stay at this vacation home in Arlington, you'll be in the mountains, just steps from Green Mountain National Forest and a 4-minute drive from Mount ...
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Private Family Estate for any Season

Private Family Estate for any Season

West Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 10-minute drive of Mount Snow and Green Mountain National Forest.
Private Family Estate for any Season
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

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

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

Wardsboro
Located in Wardsboro, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and Wardsboro Public Library.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
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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
784 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, The Jelly Mill-A Peaceful River Retreat, 8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!, By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing., Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester, Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing, Private Family Estate for any Season, Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

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
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
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
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
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 ...
Comfort Inn & Suites Brattleboro I-91
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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
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.