Holiday Rentals in Rupert

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Our top choices for Rupert holiday rentals

10.0 out of 10, Exceptional, (6 reviews)
"Great stay"
United States
Chelsea D.
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is €233
includes taxes & fees
10 Mar - 11 Mar
Cozy cabin in charming Londonderry
9.8 out of 10, Exceptional, (31 reviews)
"Great place!!"
United States
Margaret D.
Peaceful Stay at Birds of a Feather Farm & Spa

Cottage in cambridge

Peaceful Cottage Retreat
9.8 out of 10, Exceptional, (47 reviews)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
The price is €164
includes taxes & fees
1 Mar - 2 Mar
Peaceful Cottage Retreat
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is €542
includes taxes & fees
10 Mar - 11 Mar
Romantic Riverbed Treehouse - hot tub & new sauna!
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is €345
includes taxes & fees
10 Mar - 11 Mar
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful stay at a GREAT property!Couldn't ask for more!"
United States
Robert H.
The price is €325
includes taxes & fees
2 Mar - 3 Mar
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location close to ski resorts and towns. Well maintained property with all the amenities of home. Had a wonderful time staying here! "
United States
Caroline F.
The price is €302
includes taxes & fees
3 Mar - 4 Mar
6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is €299
includes taxes & fees
23 Mar - 24 Mar
Cozy Bromley Retreat
8.4 out of 10, Very good, (31 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is €306
includes taxes & fees
23 Mar - 24 Mar
Lovely ski-in/out condo steps from ski lift with trails and amazing views
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is €759
includes taxes & fees
10 Mar - 11 Mar
Insanely romantic treehouse perched next to a stream and rolling hills.
7.6 out of 10, Good, (54 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is €271
includes taxes & fees
24 Mar - 25 Mar
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
10.0 out of 10, Exceptional, (60 reviews)
"This home was spacious, super clean, and in a great location. "
United States
Des C.
The price is €205
includes taxes & fees
1 Mar - 2 Mar
Spacious apartment in beautiful, historic Arlington VT
The price is €115
includes taxes & fees
3 Mar - 4 Mar
Off-Grid Mongolian Yurt on Vermont Sheep Farm
The price is €203
includes taxes & fees
10 Mar - 11 Mar
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is €686
includes taxes & fees
10 Mar - 11 Mar
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
9.8 out of 10, Exceptional, (23 reviews)
"Nice house, clean, easy access, well set up for family skiing."
United States
L I.
The price is €632
includes taxes & fees
25 Mar - 26 Mar
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is €420
includes taxes & fees
16 Mar - 17 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
9.6 out of 10, Exceptional, (24 reviews)
"I stayed here for a few days in October with friends. We had some initial confusion with the door locks, but the hosts were able to resolve it quickly.Great location, tons of sleeping and living space, and the hot tub was a welcome addition. We had a great time and would recommend this spot."
United States
Jonathan E.
The price is €864
includes taxes & fees
24 Mar - 25 Mar
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
10.0 out of 10, Exceptional, (2 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
Stratton Woods · Secluded Vermont Cabin Retreat
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, apart-hotels, 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 €417 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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Rupert is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Rupert?

With 3 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?

Green Mountain National Forest and Merck Forest Farmland Center 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 Stratton Mountain Resort.

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.