Book Holiday Homes in Southern Vermont

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Featured Holiday Homes in Southern Vermont

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Primely Located Dover Escape < 1 Mi to Mt Snow!

Primely Located Dover Escape < 1 Mi to Mt Snow!

Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Dover
Located in East Dover, this vacation home is within a 15-minute drive of Green Mountain National Forest and North Branch Deerfield River.
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
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Cozy Cabin Between Stratton Resort & Mount Snow

Cozy Cabin Between Stratton Resort & Mount Snow

Stratton
With a stay at this vacation home in West Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Cozy Cabin Between Stratton Resort & Mount Snow
The Green Mountain Chapel // Old Church repositioned into 3 BR

The Green Mountain Chapel // Old Church repositioned into 3 BR

2 out of 5
Londonderry
With a stay at this vacation home in South Londonderry, you'll be within a 5-minute walk of West River and West River Farmers Market.
The Green Mountain Chapel // Old Church repositioned into 3 BR
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Winhall
With a stay at Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen in Stratton, you'll be within a 10-minute walk of Stratton Mountain ...
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be next to a golf course, within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

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.
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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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
644 Holiday Homes
Lowest Price
AU$238
Highest Price
AU$347
Popular accommodation
Dog-friendly chalet cabin with valley view, deck, and private hot tub, Primely Located Dover Escape < 1 Mi to Mt Snow!, Fabulous Mountain Top Retreat - 10 minutes from mount snow!, Cozy Cabin Between Stratton Resort & Mount Snow, The Green Mountain Chapel // Old Church repositioned into 3 BR, Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms, SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! , Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Top trending hotels in Southern Vermont

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 5 Jan to 6 Jan
AU$238
includes taxes & fees
5 Jan - 6 Jan 2025
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$279 per night from 8 Jan to 9 Jan
AU$279
includes taxes & fees
8 Jan - 9 Jan 2025
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
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road, Stratton, VT
The price is AU$347 per night from 20 Jan to 21 Jan
AU$347
includes taxes & fees
20 Jan - 21 Jan 2025
When you stay at The Black Bear Lodge at Stratton Mountain Resort in Stratton, you'll be next to a golf course, within a 5-minute walk of Stratton Mountain Resort ...
The Black Bear Lodge at Stratton Mountain Resort
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Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is AU$322 per night from 5 Jan to 6 Jan
AU$322
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Kimpton Taconic Hotel, an IHG Hotel in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and ...
Kimpton Taconic Hotel, an IHG Hotel
Don't see what you're looking for?
See all available properties in Southern Vermont
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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.