Rupert Holiday Rentals

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Holiday Rentals in Rupert

TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is NZ$616
includes taxes & fees
4 Jun - 5 Jun
Long Trail House at Stratton Mountain Resort
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (144)
"Home was amazing. Met all our expectations. Highly recommend property!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Property grounds
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
10.0 out of 10, Exceptional, (64)
"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
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Exterior
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
10.0 out of 10, Exceptional, (11)
"Peter and Becky were fantastic hosts. Their cottage was a home away from home. It is beautifully appointed and perfectly located. I look forward to staying here again on my next trip to Vermont."
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
Interior
Countryside 6-bedroom house centrally located
10.0 out of 10, Exceptional, (1)
"Stay was excellent, spacious. Host easy to communicate with and helpful. Reasonable price."
Countryside 6-bedroom house centrally located
Fridge, microwave, oven, stovetop
Vermont Lake House
10.0 out of 10, Exceptional, (7)
"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
Exterior
Cabin in So. Vt enjoy the Mtns.
10.0 out of 10, Exceptional, (97)
"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.
Oven, stovetop, dishwasher, coffee/tea maker
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (19)
"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 NZ$623
includes taxes & fees
31 May - 1 Jun
VT Cabin overlooking the West River and Village
Exterior
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
9.6 out of 10, Exceptional, (5)
"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
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (22)
"Beautiful home, very clean, great hosts"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.6 out of 10, Good, (40)
"Can't beat the location. We had a great stay."
The price is NZ$469
includes taxes & fees
27 May - 28 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Smart TV, books
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (28)
"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 NZ$1,800
includes taxes & fees
1 Jun - 2 Jun
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"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
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Property grounds
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
10.0 out of 10, Exceptional, (40)
"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!
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

Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (351)
"No thanks"
The price is NZ$345
includes taxes & fees
9 Jun - 10 Jun
The Equinox Golf Resort & Spa
Front of property - evening/night
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1003)
"Excellent service, comfortable bed but somewhat disappointing breakfast- waffles too dry; no scrambled eggs; large sausage cut in pieces instead of small individual sausages. I skipped it the 2nd day."
The price is NZ$274
includes taxes & fees
9 Jun - 10 Jun
Hampton Inn and Suites Manchester
Exterior
Kimpton Taconic Hotel, an IHG Hotel
4.0 star property
9.4 out of 10, Exceptional, (683)
"Our fourth stay at this property. Always a treat. Beautiful property, great service, fantastic drinks at 5 pm on the porch. Love the restaurant. Special place. "
The price is NZ$373
includes taxes & fees
9 Jun - 10 Jun
Kimpton Taconic Hotel, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Rupert holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Rupert. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Rupert. Seeing all the best attractions is bound to make you fall in love with Rupert. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Rupert short-term rentals, that won’t be hard to do.

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.

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