Rupert Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

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
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
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 ￥21,315
￥39,430 total
includes taxes & fees
Jan 15 - Jan 16
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 ￥15,631
￥38,727 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥37,799
￥78,396 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥23,447
￥57,720 total
includes taxes & fees
Jan 13 - Jan 14
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 ￥40,072
￥79,358 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥43,770
￥55,002 total
includes taxes & fees
Jan 26 - Jan 27
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 ￥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
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 12 - Jan 13
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 ￥26,999
￥38,197 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥29,699
￥102,249 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥23,210
￥68,722 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥36,458
￥67,810 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥47,367
￥59,412 total
includes taxes & fees
Jan 12 - Jan 13
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 ￥38,026
￥83,214 total
includes taxes & fees
Jan 22 - Jan 23
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 ￥39,705
￥104,168 total
includes taxes & fees
Jan 13 - Jan 14
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 ￥38,999
￥105,572 total
includes taxes & fees
Feb 9 - Feb 10
Charming Dorset Cottage Retreat.
House, 4 Bedrooms | 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 ￥39,442
￥107,694 total
includes taxes & fees
Jan 14 - Jan 15
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 ￥33,991
￥93,006 total
includes taxes & fees
Jan 12 - Jan 13
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Rupert Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"Yes"
David 1-night trip
Posted 3 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.