Rupert Holiday Rentals

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Holiday Rentals in Rupert

Aparthotel in Stratton

3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is NZ$711
includes taxes & fees
23 Nov - 24 Nov
Long Trail House at Stratton Mountain Resort

Holiday Home in Jamaica

9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
The price is NZ$1,444
includes taxes & fees
3 Dec - 4 Dec
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Cabin in Schuylerville

3.0 star property
8.6 out of 10, Excellent, (20)
"What a beautiful place it was for an escape weekend! Definitely would recommend this beautiful place!"
United States
Ana
Schuyler Yacht Basin

Holiday Home in Sunderland

10.0 out of 10, Exceptional, (126)
"Lovely home with beautiful view! Excellent host. We had a wonderful stay. "
United States
Julia P.
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Condo in Stratton

8.6 out of 10, Excellent, (27)
"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 NZ$505
includes taxes & fees
30 Nov - 1 Dec
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Cottage in Winhall

9.6 out of 10, Exceptional, (241)
"Clean and comfy. Cabin is adorable! "
United States
Roxanne M.
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Holiday Home in Manchester

10.0 out of 10, Exceptional, (58)
"Great place for a big group. Kids loved exploring and parents loved the space."
United States
John L.
Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved

Apartment in Stratton

9.4 out of 10, Exceptional, (68)
"This studio apartment is cozy and comfortable, with a balcony offering great views. The kitchen is clean and functional, and indoor parking is very convenient."
United States
GO PIN
Stratton South Long Trail Studio Adjacent to the Village and Lifts

Holiday Home in Manchester Center

10.0 out of 10, Exceptional, (207)
"This is a fabulous and incredibly special home on the most beautiful property. Extremely convenient to Manchester and Jeff is a perfect host."
United States
sari a.
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Cabin in Londonderry

8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
The price is NZ$1,010
includes taxes & fees
24 Nov - 25 Nov
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Holiday Home in Winhall

9.6 out of 10, Exceptional, (30)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
The price is NZ$1,131
includes taxes & fees
23 Nov - 24 Nov
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Holiday Home in Manchester

10.0 out of 10, Exceptional, (70)
"We had a lovely stay."
United States
Jennifer M.
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Cottage in Fort Ann

10.0 out of 10, Exceptional, (23)
"Great little get away with the family and the dogs! Met both Linda and her husband. Both very friendly and accommodating "
United States
Allan G.
The price is NZ$667
includes taxes & fees
1 Dec - 2 Dec
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Apartment in Stratton

10.0 out of 10, Exceptional, (64)
"Was a great short getaway. Place is clean and pool was great. Would recommend "
United States
Christopher M.
Long Trail House Studio at Stratton Mountain Resort

Cabin in Tinmouth

10.0 out of 10, Exceptional, (178)
"Beautiful log cabin near mountains. Quiet and relaxing vacation to get away from it all. "
United States
Sandra B.
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Cabin in londonderry

10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
The price is NZ$1,142
includes taxes & fees
27 Nov - 28 Nov
Romantic Riverbed Treehouse - hot tub & new sauna!

Holiday Home in Weston

9.8 out of 10, Exceptional, (8)
"Loved the inside and outside spaces especially the fire pit over looking the field below and the mountains in the background."
United States
Keith K.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Apartment in Whitehall

10.0 out of 10, Exceptional, (8)
"Great spot! If we're back in the area we'll stay again for sure! Really really nice room."
United States
Michael
Contemporary king w/futon

Holiday Home in Fort Ann

10.0 out of 10, Exceptional, (4)
"Check in was easy, with our host meeting us. Absolutely gorgeous kitchen with everything you need, even a separate coffee station. Very large and comfortable bathrooms with a ton of towels. Swimming pool was just perfect and sparkling with outside TV. Game room also was a lot of fun! Thank you Lisa and Michael "
United States
Natasha M.
Stay on 80 acres near Lake George w/heated pool, stables, game room - pets ok

Holiday Home in Stratton

Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball
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$505 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?

Sleep 34 in huge VT Mansion! 15 bedrms/12 bath: Xmas, Ski, weddings, family reunions, Yoga, corporate, Dogs loved: This holiday home rental outside of Rupert is located in the mountains, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 15 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.