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

The Jelly Mill-A Peaceful River Retreat

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views

Potter's Place | House in Jamaica with mountain views

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

Beautiful Custom Built Timber Frame Home, Sleeps 11

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
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 | 648 Holiday Homes |
|---|---|
Lowest Price | AU$186 |
Highest Price | AU$306 |
Popular accommodation | The Jelly Mill-A Peaceful River Retreat, Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont, LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views, Potter's Place | House in Jamaica with mountain views, Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Beautiful Custom Built Timber Frame Home, Sleeps 11, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome! |
Top trending hotels in Southern Vermont

Kimpton Taconic Hotel by IHG

Hampton Inn Brattleboro

The Equinox Golf Resort & Spa

Latchis Hotel
More ways to explore Southern Vermont
Top Picks
- Caravan Parks in Arlington
- Arlington Hotels
- Holiday Homes in Bennington
- Pet Friendly Hotels in Bennington
- Bennington Hotels
- Golf Hotels in Bondville
- Bondville Hotels
- Bromley Mountain Hotels
- Windham County Hotels
- Farmstay in Dorset
- B&B in Dorset
- Hotels with Parking in Dorset
- Dorset Hotels
- Villas in Dorset
- Holiday Homes in East Dover
- Resorts in East Dover
- Luxury Hotels in Grafton
- Pet Friendly Hotels in Grafton
- Romantic Hotels in Grafton
- Cabin Rentals in Jacksonville
- Holiday Homes in Jamaica
- Landgrove Hotels
- Ski Hotels in Londonderry
- Londonderry Hotels
- Cottages in Manchester Center
- Manchester Center Hotels
- Motels in Manchester Center
- Boutique Hotels in Manchester
- Pet Friendly Hotels in Manchester
- Manchester Hotels
- B&B in Marlboro
- Chalets in Marlboro
- Marlboro Hotels
- B&B in Mount Snow Valley
- Cabin Rentals in Mount Snow Valley
- Ski Hotels in Mount Snow Valley
- Mountain Acres Hotels
- Farmstay in Newfane
- Inns in Newfane
- Cottages in North Bennington
- North Bennington Hotels
- Resorts in Peru
- Family Hotels in Peru
- Peru Hotels
- Inns in Peru
- Saxtons River Hotels
- Cottages in Somerset
- Somerset Hotels
- Beach Hotels in Southern Vermont
- Inns in Southern Vermont
- Stamford Hotels
- Resorts in Stratton
- Family Hotels in Stratton
- Hotels with Parking in Stratton
- Luxury Hotels in Stratton
- Stratton Hotels
- Caravan Parks in Sunderland
- Guest Houses in Sunderland
- Family Hotels in Sunderland
- Inns in Sunderland
- Villas in Sunderland
- Townshend Hotels
- Wardsboro Hotels
- West Arlington Hotels
- Spa Hotels in West Dover
- West Dover Hotels
- Holiday Homes in West Wardsboro
- West Wardsboro Hotels
- Inns in West Wardsboro
- Whitingham Hotels
- Wilmington Hotels
- Cabin Rentals in Windham County
- Winhall Hotels
- Car hire near Ball Mountain Dam
- Car hire near Bennington Center for the Arts
- Car hire Cambridgeport
- Car hire near Dana L. Thompson Memorial Park
- Car hire Dorset
- Car hire Jamaica
- Car hire near Jim McGrath Gallery and Studio
- Car hire near Norman Rockwell Exhibition
- Car hire near Shaftsbury Historical Society Museum
- Car hire Stratton
- Car hire near Sunrise Express Ski Lift
- Car hire Weston
- Car hire Whitingham
- Car hire Windham
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
