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
Stay at this vacation home in Bondville. Enjoy a water park, a garden, and laundry facilities. Popular attractions Stratton Mountain Resort and Winhall River ...
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is NZ$451 per night from 25 Aug to 26 Aug
NZ$451
25 Aug - 26 Aug
includes taxes & fees
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
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall
Book a stay at this family-friendly vacation home in Bondville. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Stratton Mountain Resort ...
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
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The Mountain Escape!

The Mountain Escape!

Jamaica
Book a stay at this ski vacation home in Bondville. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Stratton Mountain Resort and Winhall ...
The Mountain Escape!
Adirondacks Family Retreat

Adirondacks Family Retreat

Fort Ann
Stay at this vacation home in Fort Ann. Enjoy laundry facilities, balconies, and cable/satellite TV service. Popular attractions Lake Hadlock and Hadlock Pond ...
Adirondacks Family Retreat
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!
Room for the whole family 8 minutes to Manchester

Room for the whole family 8 minutes to Manchester

Sunderland
Stay at this vacation home in Arlington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mount Equinox and Norman Rockwell Exhibition ...
Room for the whole family 8 minutes to Manchester
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, laundry facilities, and patios. Popular attractions Mount Snow and Stratton Mountain Resort are ...
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

Manchester
Book a stay at this family-friendly vacation home in Manchester. Enjoy private pools, a water park, and a garden. Popular attractions Museum of Creative Process ...
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
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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
NZ$281
Highest Price
NZ$451
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, Peaceful Stay at Birds of a Feather Farm & Spa , Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym, The Mountain Escape!, Adirondacks Family Retreat, Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, Room for the whole family 8 minutes to Manchester, Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes, Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

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 NZ$395 per night from 18 Aug to 19 Aug
NZ$395
18 Aug - 19 Aug
includes taxes & fees
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
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is NZ$425 per night from 1 Sept to 2 Sept
NZ$425
1 Sept - 2 Sept
includes taxes & fees
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 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 NZ$281 per night from 1 Sept to 2 Sept
NZ$281
1 Sept - 2 Sept
includes taxes & fees
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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Schuyler Yacht Basin

Schuyler Yacht Basin

3 out of 5
1 Ferry St, Schuylerville, NY
The price is NZ$335 per night from 2 Sept to 3 Sept
NZ$335
2 Sept - 3 Sept
includes taxes & fees
Stay at this 3-star cabin in Schuylerville. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Saratoga Battlefield Monument and Christ ...
Schuyler Yacht Basin
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.