Rupert Holiday Rentals

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Our top choices for Rupert holiday rentals

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 NZ$637
includes taxes & fees
19 Jan - 20 Jan
Cozy Bromley Retreat
3.0 star property
8.4 out of 10, Very good, (78 reviews)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is NZ$826
includes taxes & fees
12 Jan - 13 Jan
Long Trail House at Stratton Mountain Resort
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. "
United States
Kyle M.
The price is NZ$434
includes taxes & fees
15 Jan - 16 Jan
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
9.8 out of 10, Exceptional, (30 reviews)
"Great place!!"
United States
Margaret D.
The price is NZ$426
includes taxes & fees
12 Jan - 13 Jan
Peaceful Stay at Birds of a Feather Farm & Spa
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
The price is NZ$871
includes taxes & fees
12 Jan - 13 Jan
Stratton Mtn Studio | Renovated | Walk to Lifts
10.0 out of 10, Exceptional, (2 reviews)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is NZ$622
includes taxes & fees
13 Jan - 14 Jan
Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
8.0 out of 10, Very good, (1 review)
"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 NZ$865
includes taxes & fees
12 Jan - 13 Jan
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Apartment in Manchester Village Historic District

Grand Equinox | 2 Queen Room + Adventure Delights
8.0 out of 10, Very good, (1 review)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is NZ$580
includes taxes & fees
20 Jan - 21 Jan
Grand Equinox | 2 Queen Room + Adventure Delights
8.6 out of 10, Excellent, (27 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 NZ$758
includes taxes & fees
15 Jan - 16 Jan
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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 NZ$305
includes taxes & fees
12 Jan - 13 Jan
Peaceful Cottage Retreat
10.0 out of 10, Exceptional, (59 reviews)
"Great place—though it’s a basement, it’s nearly perfect. We’d definitely stay here again"
United States
aytac
The price is NZ$420
includes taxes & fees
12 Jan - 13 Jan
Spacious apartment in beautiful, historic Arlington VT
9.4 out of 10, Exceptional, (3 reviews)
"We had a great stay. Place was very romantic with great views. Host was responsive."
United States
Brian G.
The price is NZ$1,108
includes taxes & fees
22 Jan - 23 Jan
Romantic Riverbed Treehouse - hot tub & new sauna!
7.4 out of 10, Good, (20 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is NZ$753
includes taxes & fees
12 Jan - 13 Jan
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 NZ$745
includes taxes & fees
12 Jan - 13 Jan
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Holiday Home in Salem

ZenBarn: A Quiet Getaway
10.0 out of 10, Exceptional, (2 reviews)
"This was a great spot to stay. The ski mountain was a hour away, but this was far more affordable and the drive to Okemo is lovely."
United States
Casey O.
The price is NZ$651
includes taxes & fees
12 Jan - 13 Jan
ZenBarn: A Quiet Getaway
9.8 out of 10, Exceptional, (26 reviews)
"This was the perfect cabin to set up base for exploring the area on my New England road trip. Its vintage charm with modern upgrades set the mood perfectly to kick off October! It’s slightly off the main road, but the cabin is tucked away enough that I didn’t even notice. Great location for the local tourist attractions!"
United States
AmyC
The price is NZ$923
includes taxes & fees
22 Jan - 23 Jan
The Vermont A-Frame Mountain Retreat

Holiday Home in Sunderland

Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5 reviews)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
The price is NZ$1,171
includes taxes & fees
13 Jan - 14 Jan
Bear Pass - Mountain View by RedAwning

Holiday Home in Dorset

Charming Dorset Cottage Retreat.
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."
United States
Sarah S.
The price is NZ$1,127
includes taxes & fees
9 Feb - 10 Feb
Charming Dorset Cottage Retreat.
3.0 star property
8.0 out of 10, Very good, (1 review)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is NZ$1,190
includes taxes & fees
14 Jan - 15 Jan
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
9.6 out of 10, Exceptional, (20 reviews)
"Nice house, clean, easy access, well set up for family skiing."
United States
L I.
The price is NZ$999
includes taxes & fees
12 Jan - 13 Jan
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
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$758 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.