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

Holiday Rentals in Rupert

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Rupert holiday rentals

1. Historic Home with Colonial Charm in Manchester

Historic Home with Colonial Charm in Manchester
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful old historic house, a pleasure and treasure to get to stay there!"
United States
Mary Ann E.
The price is €349
includes taxes & fees
1 Dec - 2 Dec
Historic Home with Colonial Charm in Manchester

2. Hot Tub - Game Room - Pool Table - Kids Play Area - 2 bedroom Cabin -4 Acre Farm

Hot Tub - Game Room - Pool Table - Kids Play Area - 2 bedroom Cabin -4 Acre Farm
Granville
The price is €250
includes taxes & fees
16 Nov - 17 Nov
Hot Tub - Game Room - Pool Table - Kids Play Area - 2 bedroom Cabin -4 Acre Farm

3. 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, (27 reviews)
"Great cabin , so cozy with the wood burning stove "
United States
Susan f.
The price is €355
includes taxes & fees
14 Dec - 15 Dec
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

4. 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.
The price is €387
includes taxes & fees
1 Dec - 2 Dec
Modern Mountain Retreat w/ Chef’s Kitchen

5. Loft Apartment by the River Fort Edward (C)

Loft Apartment by the River Fort Edward (C)
Fort Edward
Loft Apartment by the River Fort Edward (C)

6. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
The price is €151
includes taxes & fees
16 Nov - 17 Nov
Off-Grid Mongolian Yurt on Vermont Sheep Farm

7. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is €243
includes taxes & fees
16 Nov - 17 Nov
Long Trail House 368 condo in Stratton Village, walk to the lifts

8. A peaceful retreat in a cabin

A peaceful retreat in a cabin
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is €158
includes taxes & fees
15 Nov - 16 Nov
A peaceful retreat in a cabin

9. Cozy Bromley Retreat — Ski-In, Ski-Out

Cozy Bromley Retreat — Ski-In, Ski-Out
Bromley Mountain
9.4 out of 10, Exceptional, (21 reviews)
"The place was clean and had all the essentials. Right across from pool and great stay."
United States
Andrew P.
The price is €401
includes taxes & fees
15 Nov - 16 Nov
Cozy Bromley Retreat — Ski-In, Ski-Out

10. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (37 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is €290
includes taxes & fees
21 Nov - 22 Nov
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

11. Founders Lodge condo at Stratton Mountain with gas fireplace

Founders Lodge condo at Stratton Mountain with gas fireplace
Stratton
8.0 out of 10, Very good, (1 review)
The price is €379
includes taxes & fees
14 Nov - 15 Nov
Founders Lodge condo at Stratton Mountain with gas fireplace

12. 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.
The price is €240
includes taxes & fees
16 Nov - 17 Nov
Spacious apartment in beautiful, historic Arlington VT

13. Peaceful 1-bedroom bungalow with AC in charming Wells

Peaceful 1-bedroom bungalow with AC in charming Wells
Wells
9.6 out of 10, Exceptional, (4 reviews)
"This is the most amazing spot. Our second time staying here after the horse races and we will definitely be back next summer. You guys are awesome!"
United States
Donna A.
The price is €229
includes taxes & fees
30 Nov - 1 Dec
Peaceful 1-bedroom bungalow with AC in charming Wells

14. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is €227
includes taxes & fees
15 Nov - 16 Nov
Fourth-floor Stratton Village studio with valley-view balcony

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

ADA King Room w/ Roll-In Shower & Views
Manchester Village Historic District
The price is €252
includes taxes & fees
23 Nov - 24 Nov
ADA King Room w/ Roll-In Shower & Views

16. Loft Apartment by the River Fort Edward (A)

Loft Apartment by the River Fort Edward (A)
Fort Edward
The price is €146
includes taxes & fees
14 Nov - 15 Nov
Loft Apartment by the River Fort Edward (A)

17. 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, (4 reviews)
"Beautiful accommodations. Great communication with host."
United States
Peggy S.
The price is €531
includes taxes & fees
15 Nov - 16 Nov
Cozy 3 Bedroom Condo in the Heart of Manchester VT

18. The Birchwood Cabin - Stunning Mountain Views

The Birchwood Cabin - Stunning Mountain Views
Sunderland
10.0 out of 10, Exceptional, (6 reviews)
"Excellent host very responsive. Beautiful cozy cabin with all the amenities you need. Highly recommend! "
United States
Robert V.
The price is €594
includes taxes & fees
9 Dec - 10 Dec
The Birchwood Cabin - Stunning Mountain Views

19. 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
The price is €398
includes taxes & fees
17 Nov - 18 Nov
Long Trail House at Stratton Mountain Resort

20. 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
The price is €434
includes taxes & fees
15 Nov - 16 Nov
Tranquil Cabin Hideaway with Firepit and Riverfront Views on the Green River in Vermont
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Rupert Hotel Reviews

Find out more about Rupert

Everything you need to know about Rupert holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rupert holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Rupert holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rupert holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rupert holiday rentals we have selected for you start as low as €151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Rupert rentals

At Expedia, we put the best Rupert holiday 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 holiday.

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. 

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?

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub: This holiday home rental outside of Rupert offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, 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 4 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. While here, R. K. Kittay Public Library and Haystack Mountain are other places worth a visit.

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.