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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
 Breaktime - Quiet and Private on dead end street

Breaktime - Quiet and Private on dead end street

Manchester
With a stay at this vacation home in Manchester, you'll be a 1-minute walk from Green Mountain National Forest and 8 minutes by foot from Golf Club at ...
Breaktime - Quiet and Private on dead end street
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
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Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$446 per night from 24 Aug to 25 Aug
AU$446
24 Aug - 25 Aug
includes taxes & fees
Located in Shaftsbury, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Shaftsbury Historical Society Museum.
Peaceful Stay at Birds of a Feather Farm & Spa
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
The price is AU$1,006 per night from 17 Aug to 18 Aug
AU$1,006
17 Aug - 18 Aug
includes taxes & fees
Located in Bondville, this vacation home is in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Bromley Mountain Ski ...
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
The Mountain Escape!

The Mountain Escape!

Jamaica
The price is AU$887 per night from 3 Sept to 4 Sept
AU$887
3 Sept - 4 Sept
includes taxes & fees
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!
Adirondacks Family Retreat

Adirondacks Family Retreat

Fort Ann
With a stay at this vacation home in Fort Ann, you'll be within a 15-minute drive of Lake George and Six Flags Great Escape.
Adirondacks Family Retreat
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Manchester Center
With a stay at this vacation home in Manchester Center, you'll be on a river, just steps from Green Mountain National Forest and a 3-minute drive from Lye Brook ...
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with  incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

shushan
The price is AU$498 per night from 6 Aug to 7 Aug
AU$498
6 Aug - 7 Aug
includes taxes & fees
Located in Cambridge, this vacation home is in the mountains, within a 5-minute drive of Battenkill River and Shushan Covered Bridge Museum.
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
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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
412 Holiday Homes
Lowest Price
AU$259
Highest Price
AU$1,006
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, Breaktime - Quiet and Private on dead end street, Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester, Peaceful Stay at Birds of a Feather Farm & Spa , Your Vermont Mountain Haven Pet Friendly home with Hot tub!, The Mountain Escape!, Adirondacks Family Retreat, Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont, Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Top trending hotels in Rupert

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is AU$325 per night from 12 Aug to 13 Aug
AU$325
12 Aug - 13 Aug
includes taxes & fees
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
The price is AU$391 per night from 20 Aug to 21 Aug
AU$391
20 Aug - 21 Aug
includes taxes & fees
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
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$259 per night from 1 Sept to 2 Sept
AU$259
1 Sept - 2 Sept
includes taxes & fees
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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Schuyler Yacht Basin

Schuyler Yacht Basin

3 out of 5
1 Ferry St, Schuylerville, NY
The price is AU$308 per night from 2 Sept to 3 Sept
AU$308
2 Sept - 3 Sept
includes taxes & fees
With a stay at Schuyler Yacht Basin in Schuylerville, you'll be a 4-minute walk from Hudson River and 12 minutes by foot from Schuylerville Family Health.
Schuyler Yacht Basin
Don't see what you're looking for?
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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.