Rupert Vacation Rentals

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Check prices for these dates

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

Our top choices for Rupert vacation rentals

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 ￥15,533
￥38,484 total
includes taxes & fees
Jan 22 - Jan 23
Peaceful Stay at Birds of a Feather Farm & Spa
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 ￥23,300
￥57,004 total
includes taxes & fees
Jan 22 - Jan 23
Beautiful country cabin with hot tub and outdoor shower in Londonderry
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 ￥14,636
￥51,538 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Bromley Retreat
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 ￥17,763
￥27,604 total
includes taxes & fees
Jan 11 - Jan 12
Peaceful Cottage 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 ￥61,387
￥76,304 total
includes taxes & fees
Jan 12 - Jan 13
Long Trail House at Stratton Mountain Resort
House (2 Bedrooms) | Interior
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
3.0 star property
Hudson Falls
The price is ￥35,459
￥102,742 total
includes taxes & fees
Jan 22 - Jan 23
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
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 ￥29,513
￥101,609 total
includes taxes & fees
Jan 15 - Jan 16
Romantic Riverbed Treehouse - hot tub & new sauna!
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 ￥39,821
￥78,506 total
includes taxes & fees
Jan 13 - Jan 14
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
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 ￥37,618
￥82,499 total
includes taxes & fees
Jan 22 - Jan 23
The Vermont A-Frame Mountain Retreat
Dining
Sowilo Retreat All Inclusive Oak House

Sowilo Retreat All Inclusive Oak House

Sowilo Retreat All Inclusive Oak House
Cambridge
9.0 out of 10, Wonderful, (2 reviews)
"One of the best getaways that I have ever experienced! The food was amazing the service was A and the scenery was absolutely breathtaking. I will definitely be returning!"
United States
Anthony
The price is ￥56,296
￥96,225 total
includes taxes & fees
Jan 11 - Jan 12
Sowilo Retreat All Inclusive Oak House
Exterior
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (23 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 ￥73,807
￥179,566 total
includes taxes & fees
Jan 19 - Jan 20
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
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 ￥36,230
￥67,386 total
includes taxes & fees
Jan 15 - Jan 16
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
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 ￥22,420
￥69,108 total
includes taxes & fees
Jan 15 - Jan 16
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Terrace/patio
The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
2.0 star property
Sunderland
10.0 out of 10, Exceptional, (2 reviews)
"This cabin was everything we could have asked for! Great, peaceful location with a beautiful view. Tastefully decorated and wonderful open concept for kitchen and living room set-up. We really enjoyed the game room downstairs, too. We will definitely be back soon."
United States
Shannon C.
The price is ￥53,547
￥121,127 total
includes taxes & fees
Feb 2 - Feb 3
The Birchwood Cabin - Stunning Mountain Views
Smart TV, fireplace, books, stereo
Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow

Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow
Jamaica
10.0 out of 10, Exceptional, (1 review)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is ￥84,792
￥108,660 total
includes taxes & fees
Jan 13 - Jan 14
Stratton A-Frame: Boot Warmers EV Hot Tub Sauna,1 Gbps, Manchester Okemo MT Snow
House (3 Bedrooms) | Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
Bondville
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Exterior
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
Manchester Center
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time."
United States
Neetesh B.
The price is ￥153,043
￥328,517 total
includes taxes & fees
Jan 21 - Jan 22
6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT
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 ￥39,456
￥103,515 total
includes taxes & fees
Jan 22 - Jan 23
Bear Pass - Mountain View by RedAwning
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 ￥23,210
￥68,722 total
includes taxes & fees
Jan 12 - Jan 13
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Dining
Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.

Sowilo Pine House. All-inclusive food and drinks.
Cambridge
10.0 out of 10, Exceptional, (4 reviews)
"BEAUTIFUL HOME GREAT VIEWS, CLEAN, SPACIOUS, AND A VERY HELPFUL PROPERTY MANAGER. CLOSE TO OUR WEDDING DESTINATION. HAD A WONDERFUL TIME. WOULD HIGHLY RECOMMEND THIS PROPERTY."
United States
diane
The price is ￥56,651
￥96,832 total
includes taxes & fees
Jan 11 - Jan 12
Sowilo Pine House. All-inclusive food and drinks.
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 Manchester View

The Manchester View

10/10 Excellent
"Yes"
David 1-night trip
Posted 2 days ago
The Manchester View

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 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.