Book Holiday Homes in Rupert

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Featured Holiday Homes in Rupert

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
Book a stay at this golf vacation home in Manchester Center. Enjoy a water park, a garden, and a pool table. Popular attractions Dana L. Thompson Memorial Park ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is NZ$455 per night from 16 Apr to 17 Apr
NZ$455
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Shaftsbury. Enjoy free WiFi, a garden, and patios. Popular attractions Howard Park and Robert Frost Stone House Museum are located ...
Peaceful Stay at Birds of a Feather Farm & Spa
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
Book a stay at this ski vacation home in Stratton. Enjoy a garden, ski-in/ski-out access, and patios. Popular attractions Stratton Mountain Resort and Stratton ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
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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
Stay at this vacation home in Rupert. Enjoy free WiFi, a garden, and patios. Popular attractions Dorset Historical Society Museum and Dorset Playhouse are located ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Manchester
Stay at this vacation home in Manchester. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Museum of Creative Process and Golf Club ...
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Mount Holly
Stay at this vacation home in Belmont. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Star Lake and Mount Holly Town Library are ...
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
7200 sf Villa & Barn on 4 Acre Manchester Estate

7200 sf Villa & Barn on 4 Acre Manchester Estate

Manchester
Stay at this vacation home in Manchester. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Southern Vermont Arts Center and American ...
7200 sf Villa & Barn on 4 Acre Manchester Estate
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
Stay at this vacation home in Stratton. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Stratton Mountain Resort and ...
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Wardsboro
Stay at this vacation home in Wardsboro. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Stratton Mountain Resort and Margie's Muse Handweaving ...
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!
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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
423 Holiday Homes
Lowest Price
NZ$208
Highest Price
NZ$455
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Peaceful Stay at Birds of a Feather Farm & Spa , Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, Dog-friendly house with picturesque mountain view & near skiing - close to Okemo, 7200 sf Villa & Barn on 4 Acre Manchester Estate, Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

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
Stay at this vacation home in Rupert. Enjoy free WiFi, a garden, and patios. Popular attractions Dorset Historical Society Museum and Dorset Playhouse are located ...
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
Fully refundableReserve now, pay when you stay
The price is NZ$309 per night from 6 Apr to 7 Apr
NZ$309
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
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 NZ$260 per night from 28 Apr to 29 Apr
NZ$260
includes taxes & fees
28 Apr - 29 Apr
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Hampton Inn and Suites Manchester
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Aspen At Manchester

Aspen At Manchester

2.5 out of 5
5669 Main Street, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is NZ$208 per night from 16 Apr to 17 Apr
NZ$208
includes taxes & fees
16 Apr - 17 Apr
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Aspen At Manchester
Don't see what you're looking for?
See all available properties in Rupert
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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.