Holiday Rentals in Rupert

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Rupert

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, 179 reviews
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, 70 reviews
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is €359
includes taxes & fees
20 Jun - 21 Jun
Long Trail House at Stratton Mountain Resort
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, 146 reviews
"Booked this terrific log cabin for its closeness to Slate Valley Trails for our annual Memorial Day Weekend mountain bike getaway. Terrific location, quiet spot on a gravel road with woods and farmlands. Great kitchen, lots of space to spread out. Very comfortable! So quiet at night, all we heard were a pair of barred owls calling to each other. Highly recommend!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Private and Artistic cabin, Pet friendly, no cleaning fee
10.0 out of 10, Exceptional, 245 reviews
"What a dream come true. This home is unlike any other and was truly the foundation for such a beautiful time shared with friends. Can’t wait to go back!"
Private and Artistic cabin, Pet friendly, no cleaning fee
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.4 out of 10, Exceptional, 18 reviews
"We enjoyed the small cabin and the view. The loft was a bit difficult to climb to. Kitchen had all supplies and we enjoyed cooking our meals and eating them with a view."
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, 19 reviews
"The cabin was perfect for a getaway! Felt secluded however walkable to small village, and within 20 minutes to Stratton. Perfectly stocked to stay in for meals!"
The price is €329
includes taxes & fees
18 Jun - 19 Jun
VT Cabin overlooking the West River and Village
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, 17 reviews
"Definitely recommend this place for large groups. Very clean, so much to do, and great communication with host. Very private location"
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, 185 reviews
"Lovely, very private property that feels far away and yet is super convenient to Manchester. Great host … everything was easy."
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, 101 reviews
"We were looking for a quick getaway to Vermont and this gorgeous home was perfect! The views are every bit as spectacular as the photos. The home is clean and modern with stunning views of the mountains from the kitchen, living room, and back deck. The living room is large and comfortable for gathering. The adjoining kitchen is clean, modern, and has everything you need to cook a meal or just prepare a quick snack. There are dishes and cooking supplies available, which made meal prep a breeze....
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, 27 reviews
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, 97 reviews
"Everything was lovely. Owners were extremely pleasant. Muffins in the morning was a great touch. We will be back."
Cabin in So. Vt enjoy the Mtns.
Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4 out of 10, Exceptional, 56 reviews
"Right across the road from Stratton Mountain. Check in was easy. Place was clean and comfortable. Much nicer and roomier than a typical hotel room. Highly recommended"
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
9.6 out of 10, Exceptional, 5 reviews
"My husband, daughter, dog and I stayed at Pete's property for the Adirondack Balloon Festival and had a great time! The whole family, including Belle the dog, were super friendly and welcoming, chatting with us, showing us around the property and even hand delivered a half dozen fresh eggs from their chickens! The property is super fun-landing somewhere between a small farm and nature compound kind of feel. We were only there a couple days and spent the majority of the time out and about because...
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, 8 reviews
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
10.0 out of 10, Exceptional, 40 reviews
"This was an amazing property. The beauty of it made for a truly wonderful weekend experience! The initial booking was smooth and effortless. Communication with the host was stellar from start to finish! When we arrived two of the caretakers were on site to greet us. They thanked us for choosing to stay, offered to help with getting settled, and gave us vital advice on preventing bobcats and bears from being attracted. hey even left some farm fresh eggs for us! Our first stop on our setup tour...
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
10.0 out of 10, Exceptional, 64 reviews
"Wonderful property to rest and relax in nature. This was our second year staying at Rik's magical treehouse and we will continue to do so. Rik is a fantastic host and we feel blessed that he shares it with others."
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, 28 reviews
"Super clean and tidy. Good location with 5 nearby ski mountains. The listing does not state that the indoor fireplace can not be used; so we were disappointed to discover that on arrival."
The price is €814
includes taxes & fees
18 Jun - 19 Jun
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, 44 reviews
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Vermont Lake House
10.0 out of 10, Exceptional, 7 reviews
"Very well appointed, beautifully decorated and in a great location within 15 min of town. Plenty of sleeping room with 3 bedrooms on the main floor and 1 in the finished basement. Outdoor space was special. Deck has 5 comfortable Adirondack chairs with tables, picnic table, and quality gas grill. Also additional seating on the lawn overlooking the water with a fire pit. There was road noise from the other side of the pond but not so much that it was a nuisance. We used the 4 kayaks a lot. There...
Vermont Lake House
Don't see what you're looking for?
See all available properties in Rupert
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.

Other types of properties in Rupert you may be interested in

The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, 357 reviews
"Nice room. High Ceilings. Responsive staff. "
The price is €201
includes taxes & fees
23 Jun - 24 Jun
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel, an IHG Hotel
4.0 star property
9.4 out of 10, Exceptional, 689 reviews
"Everything was great with the exception of the pool towels. I make this comment every time as they are threadbare and small. Everything else at the hotel is excellent."
The price is €220
includes taxes & fees
23 Jun - 24 Jun
Kimpton Taconic Hotel, an IHG Hotel
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, 1,011 reviews
"Very clean large room with plenty of parking and located within walking distance downtown Manchester."
The price is €156
includes taxes & fees
30 Jun - 1 Jul
Hampton Inn and Suites 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.

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 €329 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?

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly: This holiday home rental outside of Rupert offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Rupert?

With 3 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?

While exploring the area, visit family-friendly sights like Sugar Shack, or get outside and enjoy nature at Merck Forest Farmland Center. In the wider area, you’ll find Dorset Playhouse and Equinox Preservation Trust.

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.

Recent reviews of Rupert properties
Expedia verified reviews