Book Holiday Homes in Rupert

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Featured Holiday Homes in Rupert

Cozy Cabin Between Stratton Resort & Mount Snow

Cozy Cabin Between Stratton Resort & Mount Snow

Stratton
Stay at this vacation home in West Wardsboro. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Stratton Mountain Resort and Mount Snow ...
Cozy Cabin Between Stratton Resort & Mount Snow
The Green Mountain Chapel // Old Church repositioned into 3 BR

The Green Mountain Chapel // Old Church repositioned into 3 BR

2 out of 5
Londonderry
Stay at this vacation home in South Londonderry. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions West River and West River Farmers Market ...
The Green Mountain Chapel // Old Church repositioned into 3 BR
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
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Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro
Book a stay at this golf vacation home in Wardsboro. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Stratton Mountain Resort and Margie's ...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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 Playhouse and Merck Forest Farmland Center are located ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

West Wardsboro
Stay at this vacation home in West Wardsboro. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Mount Snow and Stratton Mountain Resort ...
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Manchester
Book a stay at this golf vacation home in Manchester. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Golf ...
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

Jamaica
Stay at this vacation home in Jamaica. Enjoy an in-room coffeemaker, in-room fireplaces, and a spa tub. Popular attractions Stratton Mountain Resort and Solstice ...
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Jamaica
Stay at this vacation home in Jamaica. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Stratton Mountain Resort and Jamaica State ...
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi
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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
345 Holiday Homes
Lowest Price
NZ$263
Highest Price
NZ$392
Popular accommodation
Cozy Cabin Between Stratton Resort & Mount Snow, The Green Mountain Chapel // Old Church repositioned into 3 BR, Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes, Miner Cottage-Historic Antique Home just steps from the Equinox Resort, 5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!, Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Top trending hotels in Rupert

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$263 per night from 5 Jan to 6 Jan
NZ$263
includes taxes & fees
5 Jan - 6 Jan 2025
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
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road, Stratton, VT
The price is NZ$384 per night from 20 Jan to 21 Jan
NZ$384
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this 3-star ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
The Black Bear Lodge at Stratton Mountain Resort
Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is NZ$356 per night from 5 Jan to 6 Jan
NZ$356
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
Kimpton Taconic Hotel, an IHG Hotel
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The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
The price is NZ$392 per night from 5 Jan to 6 Jan
NZ$392
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.