Rupert Vacation Rentals

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Check prices for these dates

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

Our top choices for Rupert vacation 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.
The price is ￥14,032
￥29,246 total
includes taxes & fees
Feb 26 - Feb 27
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 ￥21,749
￥43,077 total
includes taxes & fees
Feb 26 - Feb 27
Cozy cabin in charming Londonderry
Terrace/patio

Vacation 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 ￥19,489
￥29,767 total
includes taxes & fees
Feb 26 - Feb 27
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 ￥29,327
￥101,144 total
includes taxes & fees
Mar 2 - Mar 3
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 ￥23,387
￥61,551 total
includes taxes & fees
Mar 10 - Mar 11
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 ￥30,028
￥59,116 total
includes taxes & fees
Feb 26 - Feb 27
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, (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 ￥23,153
￥56,292 total
includes taxes & fees
Feb 26 - Feb 27
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 ￥16,862
￥54,268 total
includes taxes & fees
Mar 23 - Mar 24
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 ￥17,150
￥56,255 total
includes taxes & fees
Mar 23 - Mar 24
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 ￥61,740
￥137,243 total
includes taxes & fees
Feb 26 - Feb 27
Insanely romantic treehouse perched next to a stream and rolling hills.
Interior

Vacation 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 ￥19,801
￥49,982 total
includes taxes & fees
Mar 24 - Mar 25
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 ￥26,661
￥37,718 total
includes taxes & fees
Feb 26 - Feb 27
Spacious apartment in beautiful, historic Arlington VT
Outdoor dining

Cabin in Poultney

Off-Grid Mongolian Yurt on Vermont Sheep Farm
The price is ￥13,611
￥20,484 total
includes taxes & fees
Mar 3 - Mar 4
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 ￥15,123
￥34,844 total
includes taxes & fees
Mar 3 - Mar 4
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 ￥59,636
￥127,115 total
includes taxes & fees
Mar 3 - Mar 4
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 ￥50,683
￥114,177 total
includes taxes & fees
Feb 26 - Feb 27
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Fridge, oven, stovetop, dishwasher

Vacation 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 ￥39,570
￥76,426 total
includes taxes & fees
Mar 25 - Mar 26
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Exterior

Vacation Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
9.6 out of 10, Exceptional, (24 reviews)
"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "
United States
Lee Anna C.
The price is ￥52,389
￥161,030 total
includes taxes & fees
Mar 24 - Mar 25
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Interior

Vacation 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 ￥18,709
￥61,792 total
includes taxes & fees
Mar 24 - Mar 25
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 Olympia Lodge

The Olympia Lodge

10/10 Excellent
"Our room was super comfortable and very clean. The owners were so kind and accommodating. The breakfast in the morning was made to order and such an excellent way to start our day of snowboarding. The next time we visit the area we are definitely staying at The Olympia Lodge. "
Michele 1-night trip
Posted 2 days ago
The Olympia Lodge

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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  • 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 vacation rentals in Rupert?

Yes, we give you a choice of vacation rentals near popular local attractions in Rupert, or you can go with a more secluded option if you're looking for a relaxing stay. Rupert is known for its parks.

What are some of the best vacation rentals in Rupert?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This vacation home rental outside of Rupert is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Rupert?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find R. K. Kittay Public Library and Stratton Mountain Resort.

What’s a vacation rental in Rupert like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Rupert. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.