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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
Holiday Homes
Lowest Price
AU$223
Highest Price
AU$348
Popular accommodation
The Equinox Golf Resort & Spa, Kimpton Taconic Hotel, an IHG Hotel, The Black Bear Lodge at Stratton Mountain Resort, Aspen At Manchester

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
The price is AU$338 per night from 3 Mar to 4 Mar
AU$338
includes taxes & fees
3 Mar - 4 Mar
When you a stay at The Equinox Golf Resort & Spa in Manchester, you'll be in the mountains, just steps from Green Mountain National Forest and Golf Club at ...
The Equinox Golf Resort & Spa
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 AU$338 per night from 23 Feb to 24 Feb
AU$338
includes taxes & fees
23 Feb - 24 Feb
With a stay at Kimpton Taconic Hotel, an IHG Hotel in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and ...
Kimpton Taconic Hotel, an IHG Hotel
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 AU$348 per night from 2 Mar to 3 Mar
AU$348
includes taxes & fees
2 Mar - 3 Mar
When you stay at The Black Bear Lodge at Stratton Mountain Resort in Stratton, you'll be next to a golf course, within a 5-minute walk of Stratton Mountain Resort ...
The Black Bear Lodge at Stratton Mountain Resort
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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 AU$223 per night from 25 Feb to 26 Feb
AU$223
includes taxes & fees
25 Feb - 26 Feb
With a stay at Aspen At Manchester in Manchester Center, you'll be in the entertainment district, just steps from Green Mountain National Forest and a 2-minute ...
Aspen At Manchester
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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.