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

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!
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 |
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Lowest Price | AU$190 |
Highest Price | AU$420 |
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 Locations for Holiday Homes in Rupert
More accommodations in Rupert
Top trending hotels in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

The Equinox Golf Resort & Spa

Hampton Inn and Suites Manchester

Aspen At Manchester
More ways to explore Rupert
Top picks
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^Subject to availability and chosen travel dates.