A rural landscape with a barn on a hill, surrounded by autumn-colored trees.

Rupert Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Rupert vacation rentals

Property grounds

1. Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (66 reviews)
"Excellent place, fantastic hosts, highly recommend."
United States
Mike K.
$243 nightly
The price is $272
Oct 19 - Oct 20
Total with taxes and fees
Spacious apartment in beautiful, historic Arlington VT
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

2. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
$391 nightly
The price is $441
Oct 18 - Oct 19
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A wooden deck with a white lattice base, a metal roof, and a house with a garage door in the background.

3. Beautiful 1-bedroom cabin with AC in wonderful Wells

Beautiful 1-bedroom cabin with AC in wonderful Wells
Wells
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location with Mountain views. Property owners were wonderful hosts."
United States
Jane
$133 nightly
The price is $148
Oct 18 - Oct 19
Total with taxes and fees
Beautiful 1-bedroom cabin with AC in wonderful Wells
An outdoor dining area with tables and umbrellas, a wooden fence, and a building with large windows and lights.

4. Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.

Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
Manchester
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful cozy house with plenty of beds and space. We drove here in a snowstorm and were so thankful that the host had cleared the driveway and walkways for us. Overall a great stay."
United States
Greg W.
$474 nightly
The price is $536
Oct 18 - Oct 19
Total with taxes and fees
Downtown Manchester Center. SKI Bromley in 12 min, Stratton Mountain in 25 min.
A cabin with a sloped roof, large windows, and a balcony with outdoor seating.

5. Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
shushan
9.6 out of 10, Exceptional, (25 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
$315 nightly
The price is $350
Oct 19 - Oct 20
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
A room with a large window, a wooden table, two chairs, and a woven basket on the table.

6. Cozy 3 Bedroom Condo in the Heart of Manchester VT

Cozy 3 Bedroom Condo in the Heart of Manchester VT
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful place Very spacious and super organized we love our stay "
United States
Rafael
$606 nightly
The price is $616
Oct 19 - Oct 20
Total with taxes and fees
Cozy 3 Bedroom Condo in the Heart of Manchester VT
A cozy log cabin interior with a sofa, dining table, and a wood-burning stove.

7. Hilltop Cottage

Hilltop Cottage
Argyle
10.0 out of 10, Exceptional, (3 reviews)
"great place to stay"
United States
Anna Z.
$789 nightly
The price is $876
Oct 18 - Oct 19
Total with taxes and fees
Hilltop Cottage
A bedroom with a bed, a window, and a door.

8. Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
9.0 out of 10, Wonderful, (26 reviews)
"Love this place and the ease of the check in and check out! Quiet and peaceful! Would have like to seen the pub open though! See you all next year!"
United States
Jean Paul
$221 nightly
The price is $243
Oct 18 - Oct 19
Total with taxes and fees
Schuyler Yacht Basin
A dining room with a wooden table, four chairs, a vase with flowers, and a view of greenery outside.

9. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were absolutely amazing. We had a wonderful time. The home is beautiful. The host is very communicative."
United States
Victor G.
$351 nightly
The price is $397
Nov 3 - Nov 4
Total with taxes and fees
Historic Home with Colonial Charm in Manchester
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a view to the dining area.

10. Modern Mountain Retreat w/ Chef’s Kitchen

Modern Mountain Retreat w/ Chef’s Kitchen
Manchester
10.0 out of 10, Exceptional, (1 review)
"Communication with Caroline was top notch and speedy! Very clear instructions for accessing the property and check out. Even though this place is connected with two other rooms/units ( I think that is what it is) we never heard them and hopefully we didn't bother them either!The house was amazing inside and out. The location was exceptional!Thank you for a beautiful stay!"
United States
Eva G.
$392 nightly
The price is $443
Nov 3 - Nov 4
Total with taxes and fees
Modern Mountain Retreat w/ Chef’s Kitchen
Terrace/patio

11. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (4 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
$571 nightly
The price is $640
Oct 28 - Oct 29
Total with taxes and fees
The Birchwood Cabin - Stunning Mountain Views
A two-story white house with a front porch, a door with a wreath, and a chimney.

12. Cozy farmhouse in Manchester - short drive to multiple ski mountains!

Cozy farmhouse in Manchester - short drive to multiple ski mountains!
Manchester
9.4 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and responsive during our stay. Loved that the house is close to the main town as well as close to the ski slopes (Bromley). "
United States
Marissa H.
$661 nightly
The price is $747
Oct 24 - Oct 25
Total with taxes and fees
Cozy farmhouse in Manchester - short drive to multiple ski mountains!
A white building with green shutters, a covered porch, and a landscaped garden with flowers.

13. ADA King Room w/ Roll-In Shower & Views

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
$226 nightly
The price is $249
Nov 4 - Nov 5
Total with taxes and fees
ADA King Room w/ Roll-In Shower & Views
A playground with slides and climbing structures surrounded by trees.

14. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"Nice place "
United States
Janja L.
$333 nightly
The price is $376
Oct 26 - Oct 27
Total with taxes and fees
Cozy Bromley Retreat
A hot tub surrounded by stone steps, wooden lounge chairs, and a wooden deck.

15. Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (43 reviews)
"Our family had a wonderful vacation. The house and location were great. We will come back."
United States
Victoria L.
$591 nightly
The price is $663
Oct 19 - Oct 20
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
A red barn, a hammock, a fire pit, and a chair in a grassy area with trees and a stream in the background.

16. Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont

Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
Sandgate
$254 nightly
The price is $287
Oct 20 - Oct 21
Total with taxes and fees
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

17. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (37 reviews)
"Great space, great location!"
United States
Jason S.
$412 nightly
The price is $466
Oct 19 - Oct 20
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A covered picnic area with benches and a paved walkway.

18. Cozy 2 bedroom apartment near Lake George

Cozy 2 bedroom apartment near Lake George
Fort Ann
10.0 out of 10, Exceptional, (1 review)
"Bedrooms and bathroom should have locks for privacy.Small table on screen porch.More chairs to accommodate eating together in kitchen."
United States
Jerome R.
$314 nightly
The price is $348
Oct 18 - Oct 19
Total with taxes and fees
Cozy 2 bedroom apartment near Lake George
A room with a wooden coffee table, two white chairs, and a carpeted floor.

19. Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont

Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
Winhall
10.0 out of 10, Exceptional, (1 review)
"Sierra was great to work with upon check in. We really enjoyed our stay."
United States
Jonathan W. B.
$506 nightly
The price is $572
Oct 19 - Oct 20
Total with taxes and fees
Mountain Retreat with Outdoor Living Space and Ping Pong Table in Vermont
An outdoor dining area with a wooden deck, a table set with plates, glasses, and a vase of flowers.

20. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
$621 nightly
The price is $696
Nov 1 - Nov 2
Total with taxes and fees
Tranquil Brookside Retreat with Hot Tub & Firepit
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
"I have stayed here many times when visiting Stratton. However, this time , the room I requested was over booked. But that was ok. The front desk staff was so accommodating. They gave us a 2 bedroom 2 bath condo !!! Total score !!!"
Kathleen 2-night trip
Posted 1 hour ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Rupert

Everything you need to know about Rupert vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Rupert vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rupert vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rupert vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rupert. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Rupert in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Rupert rentals

At Expedia, we put the best Rupert vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Rupert rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rupert vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rupert. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub: This vacation home rental outside of Rupert offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 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 balcony, 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 4 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?

Merck Forest Farmland Center and Green Mountain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, R. K. Kittay Public Library and Haystack Mountain are other places worth a visit.

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.