A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

Rupert Holiday Rentals

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Our top choices for Rupert holiday rentals

Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
8.6 out of 10, Excellent, (20 reviews)
"Great place to stay while visiting the area!"
United States
David R.
The price is NZ$420
includes taxes & fees
14 July - 15 July
Schuyler Yacht Basin

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (35 reviews)
"Great place"
United States
Aidan K.
The price is NZ$478
includes taxes & fees
27 July - 28 July
Peaceful getaway at birds of a feather

The MountainTop - Stratton & Mt Snow - Fire Pit

The MountainTop - Stratton & Mt Snow - Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
The price is NZ$721
includes taxes & fees
11 Aug - 12 Aug
The MountainTop - Stratton & Mt Snow - Fire Pit

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
The price is NZ$681
includes taxes & fees
18 July - 19 July
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (14 reviews)
"Nice place "
United States
Janja L.
The price is NZ$558
includes taxes & fees
14 July - 15 July
Cozy Bromley Retreat

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay as always. "
United States
debbie r.
The price is NZ$302
includes taxes & fees
14 July - 15 July
Quiet Apt. close to Okemo and Killington. Off Rt. 7 with private driveway.

Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (59 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is NZ$747
includes taxes & fees
23 July - 24 July
Quaint, friendly cottage with lakefront location & water views

Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is NZ$670
includes taxes & fees
26 July - 27 July
Comfy Cottage with Private Hot Tub in Historic East Poultney

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is NZ$972
includes taxes & fees
14 July - 15 July
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (23 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is NZ$601
includes taxes & fees
14 July - 15 July
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Romantic New York Getaway near the Adirondacks

Romantic New York Getaway near the Adirondacks
Cambridge
The price is NZ$237
includes taxes & fees
20 July - 21 July
Romantic New York Getaway near the Adirondacks

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"House was perfect for a guys trip for skiing. Just as expected. Would stay again. "
United States
Michael A.
The price is NZ$1,398
includes taxes & fees
15 July - 16 July
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is NZ$499
includes taxes & fees
14 July - 15 July
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is NZ$440
includes taxes & fees
14 July - 15 July
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (35 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is NZ$573
includes taxes & fees
19 July - 20 July
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Runamuk Farm Camp Tiny House near Cambridge, New York

Runamuk Farm Camp Tiny House near Cambridge, New York
Cambridge
The price is NZ$237
includes taxes & fees
19 July - 20 July
Runamuk Farm Camp Tiny House near Cambridge, New York

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (31 reviews)
"Great space, great location!"
United States
Jason S.
The price is NZ$681
includes taxes & fees
14 July - 15 July
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"Everything about our stay was top notch. Highly recommend and I will book this house again. "
United States
samantha b.
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Long Trail House South Wing 2B2B Condo

Long Trail House South Wing 2B2B Condo
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"Very clean 2br 2ba condo in excellent location. Host provided detailed important information that helped us find property and how to access unit. I would definitely recommend staying here."
United States
Eileen R.
The price is NZ$692
includes taxes & fees
19 July - 20 July
Long Trail House South Wing 2B2B Condo

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy with a working hot tub. Would highly recommend"
United States
Justin E.
The price is NZ$659
includes taxes & fees
14 July - 15 July
Cozy Moonship Yurt in the woods
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.
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Top Rupert Hotel Reviews

Find out more about Rupert

Everything you need to know about Rupert holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rupert holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rupert holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rupert holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rupert. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rupert holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rupert holiday rentals we have selected for you start as low as NZ$420 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rupert rentals

At Expedia, we put the best Rupert holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rupert rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rupert holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rupert. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Rupert?

Yes, there are holiday rentals close to the most popular sights in Rupert, or you can select a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best holiday rentals that Rupert has to offer?

Riverfront 2-bedroom house with tons of light, AC, deck & patio. Pet Friendly: This holiday home rental outside of Rupert is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Rupert?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Rupert stay.

What’s there to see and do in Rupert?

Merck Forest Farmland Center and Green Mountain National Forest are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find R. K. Kittay Public Library and Equinox Preservation Trust.

What’s a holiday rental in Rupert like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rupert. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family gatherings.