Rupert Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Rupert holiday rentals

Exterior

Cabin in Jamaica

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
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
Interior

Cabin in Londonderry

Cozy cabin in charming Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is HK$1,091
HK$2,170 total
includes taxes & fees
2 Mar - 3 Mar
Cozy cabin in charming Londonderry
Terrace/patio

Holiday Home in Shaftsbury

Peaceful Stay at Birds of a Feather Farm & Spa
9.8 out of 10, Exceptional, (31 reviews)
"Great place!!"
United States
Margaret D.
Peaceful Stay at Birds of a Feather Farm & Spa
TV, books

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 HK$978
HK$1,476 total
includes taxes & fees
1 Mar - 2 Mar
Peaceful Cottage Retreat
Exterior

Cabin in londonderry

Romantic Riverbed Treehouse - hot tub & new sauna!
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is HK$1,472
HK$5,075 total
includes taxes & fees
2 Mar - 3 Mar
Romantic Riverbed Treehouse - hot tub & new sauna!
Property grounds

Condo in Stratton

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is HK$1,260
HK$3,212 total
includes taxes & fees
17 Mar - 18 Mar
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Property grounds

Cottage in Fort Ann

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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$1,507
HK$2,992 total
includes taxes & fees
2 Mar - 3 Mar
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Smart TV, fireplace, books, computer monitors

Condo in Winhall

6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
10.0 out of 10, Exceptional, (22 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 HK$1,162
HK$2,825 total
includes taxes & fees
3 Mar - 4 Mar
6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
Children’s area

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 HK$846
HK$2,723 total
includes taxes & fees
25 Mar - 26 Mar
Cozy Bromley Retreat
Property grounds

Condo in Stratton

Lovely ski-in/out condo steps from ski lift with trails and amazing views
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 HK$853
HK$2,804 total
includes taxes & fees
23 Mar - 24 Mar
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Exterior

Cabin in Londonderry

Insanely romantic treehouse perched next to a stream and rolling hills.
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is HK$3,098
HK$6,966 total
includes taxes & fees
2 Mar - 3 Mar
Insanely romantic treehouse perched next to a stream and rolling hills.
Interior

Holiday Home in Stratton

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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 HK$986
HK$2,516 total
includes taxes & fees
24 Mar - 25 Mar
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Property grounds

Apartment in Arlington

Spacious apartment in beautiful, historic Arlington VT
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 HK$1,338
HK$1,893 total
includes taxes & fees
2 Mar - 3 Mar
Spacious apartment in beautiful, historic Arlington VT
Outdoor dining

Cabin in Poultney

Off-Grid Mongolian Yurt on Vermont Sheep Farm
The price is HK$683
HK$1,028 total
includes taxes & fees
3 Mar - 4 Mar
Off-Grid Mongolian Yurt on Vermont Sheep Farm

Apartment in Stratton

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
The price is HK$767
HK$1,758 total
includes taxes & fees
3 Mar - 4 Mar
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Smart TV, fireplace

Cabin in Londonderry

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is HK$2,992
HK$6,378 total
includes taxes & fees
3 Mar - 4 Mar
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Interior

Cabin in Londonderry

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
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 HK$1,648
HK$4,593 total
includes taxes & fees
2 Mar - 3 Mar
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Fridge, oven, stovetop, dishwasher

Holiday Home in Londonderry

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
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 HK$1,986
HK$3,782 total
includes taxes & fees
16 Mar - 17 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Exterior

Holiday Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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 HK$2,438
HK$7,838 total
includes taxes & fees
24 Mar - 25 Mar
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Interior

Holiday Home in Wardsboro

Stratton Woods · Secluded Vermont Cabin Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is HK$978
HK$3,140 total
includes taxes & fees
24 Mar - 25 Mar
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"We loved our stay at the Black Bear! The check-in went smoothly with desk staff, Noah. She was very helpful and went over everything about our stay. The room was very clean. The hot tub was very nice and clean and a welcome after a day on the slopes. The shuttle to the mountain was great and ran frequently. The breakfast was always hot and had many options. We would definitely stay there again!"
Nancy 3-night trip
Posted 1 day ago
The Black Bear Lodge at Stratton Mountain Resort

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:

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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?

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 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.