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

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!
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 |
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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 Locations for Holiday Homes in Southern Vermont
More accommodations in Southern Vermont
Top trending hotels in Southern Vermont

The Equinox Golf Resort & Spa

Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro
More ways to explore Southern Vermont
Top picks
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^Subject to availability and chosen travel dates.