Book Holiday Homes in Rupert

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Featured Holiday Homes in Rupert

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
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!
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.
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2 Mi to Hoosic River: 'The Moss House' w/ Deck!

2 Mi to Hoosic River: 'The Moss House' w/ Deck!

Eagle Bridge
With a stay at this vacation home in Eagle Bridge, you'll be within a 15-minute drive of Eldridge Swamp State Forest and Bennington Battlefield Park.
2 Mi to Hoosic River: 'The Moss House' w/ Deck!
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
With a stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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
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!
The Mountain Escape!

The Mountain Escape!

Jamaica
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!
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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.

Rupert 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 Rupert vacation homes are the perfect way for you to wing it.

Holiday houses in Rupert 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 Rupert 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 Rupert adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Rupert 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 Rupert 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.

Rupert Holiday Homes essential information

Accommodation
420 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, 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., 2 Mi to Hoosic River: 'The Moss House' w/ Deck!, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, 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, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!, The Mountain Escape!

Top trending hotels in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
With a stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
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 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
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
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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.