Book Holiday Homes in Rupert
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Featured Holiday Homes in Rupert

Peaceful Stay at Birds of a Feather Farm & Spa

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

3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

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

LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views

6 Bed 6 Bath | Hot Tub | Arcade | 16 min Okemo

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
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 | 366 Holiday Homes |
|---|---|
Lowest Price | NZ$238 |
Highest Price | NZ$438 |
Popular accommodation | Peaceful Stay at Birds of a Feather Farm & Spa , Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, 3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit, Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont, Starry Skies: 7min to SkiStratton+PikesFalls+DogOK, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms, LUXURY - 2 Sauna - Hot Tub - Gym - Fireplace - Roman Bath Private Lake Views, 6 Bed 6 Bath | Hot Tub | Arcade | 16 min Okemo, Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes |
Top trending hotels in Rupert

Hampton Inn and Suites Manchester

The Palmer House Resort, an Ascend Collection Hotel

The Equinox Golf Resort & Spa

Kimpton Taconic Hotel by IHG
More ways to explore Rupert
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
