Rupert Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Rupert holiday rentals

Children’s area
Cozy Bromley Retreat

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
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 HK$707
HK$2,534 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Bromley Retreat
Outdoor spa tub
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
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 HK$2,968
HK$3,689 total
includes taxes & fees
12 Jan - 13 Jan
Long Trail House at Stratton Mountain Resort
Property grounds
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
Jamaica
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 HK$1,052
HK$1,947 total
includes taxes & fees
15 Jan - 16 Jan
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Terrace/patio
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa
Shaftsbury
9.8 out of 10, Exceptional, (30 reviews)
"Great place!!"
United States
Margaret D.
The price is HK$772
HK$1,912 total
includes taxes & fees
12 Jan - 13 Jan
Peaceful Stay at Birds of a Feather Farm & Spa
Fridge, microwave, oven, stovetop
Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
The price is HK$1,866
HK$3,870 total
includes taxes & fees
12 Jan - 13 Jan
Stratton Mtn Studio | Renovated | Walk to Lifts
Interior
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
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 HK$1,158
HK$2,849 total
includes taxes & fees
13 Jan - 14 Jan
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Fridge, oven, stovetop, dishwasher
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
Londonderry
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 HK$1,978
HK$3,918 total
includes taxes & fees
12 Jan - 13 Jan
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Indoor pool, a heated pool
Grand Equinox | 2 Queen Room + Adventure Delights

Grand Equinox | 2 Queen Room + Adventure Delights

Grand Equinox | 2 Queen Room + Adventure Delights
Manchester Village Historic District
8.0 out of 10, Very good, (1 review)
"Yes, but you have to drive to town "
United States
Cathy W.
The price is HK$2,161
HK$2,715 total
includes taxes & fees
20 Jan - 21 Jan
Grand Equinox | 2 Queen Room + Adventure Delights
Property grounds
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

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
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 HK$1,107
HK$3,412 total
includes taxes & fees
15 Jan - 16 Jan
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV, books
Peaceful Cottage Retreat

Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
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 HK$877
HK$1,363 total
includes taxes & fees
12 Jan - 13 Jan
Peaceful Cottage Retreat
Property grounds
Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
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 HK$1,333
HK$1,886 total
includes taxes & fees
12 Jan - 13 Jan
Spacious apartment in beautiful, historic Arlington VT
Exterior
Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
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 HK$1,466
HK$5,048 total
includes taxes & fees
12 Jan - 13 Jan
Romantic Riverbed Treehouse - hot tub & new sauna!
Property grounds
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (20 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is HK$1,146
HK$3,393 total
includes taxes & fees
12 Jan - 13 Jan
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Property grounds
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Fort Ann
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 HK$1,800
HK$3,348 total
includes taxes & fees
12 Jan - 13 Jan
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Interior
ZenBarn: A Quiet Getaway

ZenBarn: A Quiet Getaway

ZenBarn: A Quiet Getaway
Salem
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 HK$2,338
HK$2,933 total
includes taxes & fees
12 Jan - 13 Jan
ZenBarn: A Quiet Getaway
Exterior
The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat

The Vermont A-Frame Mountain Retreat
Winhall
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 HK$1,877
HK$4,108 total
includes taxes & fees
22 Jan - 23 Jan
The Vermont A-Frame Mountain Retreat
Interior
Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning

Bear Pass - Mountain View by RedAwning
Sunderland
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 HK$1,960
HK$5,142 total
includes taxes & fees
13 Jan - 14 Jan
Bear Pass - Mountain View by RedAwning
Exterior detail
Charming Dorset Cottage Retreat.

Charming Dorset Cottage Retreat.

Charming Dorset Cottage Retreat.
2.0 star property
Dorset
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 HK$1,925
HK$5,212 total
includes taxes & fees
9 Feb - 10 Feb
Charming Dorset Cottage Retreat.
View from property
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
Arlington
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 HK$1,948
HK$5,317 total
includes taxes & fees
14 Jan - 15 Jan
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Interior
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

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, (20 reviews)
"Nice house, clean, easy access, well set up for family skiing."
United States
L I.
The price is HK$1,613
HK$4,509 total
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

Toll Road Inn

Toll Road Inn

10/10 Excellent
"Everything was/is perfect. Couldn’t recommend more. "
Nicholas 1-night trip
Posted 17 hours ago
Toll Road Inn

Find out more about Rupert

Search for holiday rentals in Rupert on Expedia! You can easily find your home rentals, villas, holiday apartments in Rupert using one of the methods below:

  • View our selection of featured holiday rentals in Rupert
  • Use the map to find apartments and other holiday homes in the Rupert neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Rupert while they last

Look no further and take a look at our great range of rental properties in Rupert!

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.