Rupert Vacation Rentals

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Vacation Rentals in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
10.0 out of 10, Exceptional, (149)
"My family and I loved our stay in Creekside Camp! The location was beautiful, the cabin was gorgeous and the hot tub by the creek was the cherry on top. Dan, the property owner, communicated quickly and went above and beyond if we had any issues. All and all it was the perfect relaxing getaway and we can't wait to come back again!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (69)
"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 $317
$384 total
includes taxes & fees
Jun 6 - Jun 7
Long Trail House at Stratton Mountain Resort
Private and Artistic cabin, Pet friendly, no cleaning fee
Property grounds
Private and Artistic cabin, Pet friendly, no cleaning fee
10.0 out of 10, Exceptional, (244)
"We had a great stay at this cabin and the property. It's everything the write up says and then some. The owner is a true craftsman with an eye for creativity and for bringing the outside in. I wish I had taken a photo of my review that I left him handwritten in his leather bound book to share with you here. He has thought of everything to provide a peaceful, calm and tranquil getaway. There is so much wildlife to be seen and heard. The cabin is rustic and gave me Hobbit and fairytale vibes. We...
Private and Artistic cabin, Pet friendly, no cleaning fee
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Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (179)
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
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
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (145)
"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.
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Property grounds
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (185)
"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
VT Cabin overlooking the West River and Village
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 $169
$343 total
includes taxes & fees
Jun 7 - Jun 8
VT Cabin overlooking the West River and Village
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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
Vermont Treehouse compound: no cleaning fee. Spend a few days In the Trees
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
Countryside 6-bedroom house centrally located
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
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Property grounds
Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4 out of 10, Exceptional, (56)
"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
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
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (23)
"Excellent house in a cute town. Went with a 5 friends - there was plenty of space for everyone to sleep and relax around the house. Very well maintained, very clean, and nice homey touches. Very easy to get in, and get everything to work (hot tub, sauna, etc). Felt like home away from home. Would definitely recommend!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
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 $399
$1,101 total
includes taxes & fees
Jun 6 - Jun 7
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
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
Dragonfly Cottage -Luxurious Mountain View A-Frame -quiet street close to town.
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.
Green Mountain Modern House: iconic modern getaway
Exterior
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!
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!
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, (101)
"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
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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.

Rupert Vacation Rental Travel Info

Popular accommodation
Rupert private vacation homes
Known landmarks
Dorset Playhouse and Merck Forest Farmland Center
International airports
Springfield, VT (VSF-Hartness State) and Burlington, VT (BTV-Burlington Intl.)

Other types of properties in Rupert you may be interested in

The Equinox Golf Resort & Spa
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (353)
"No thanks"
The price is $179
$248 total
includes taxes & fees
Jun 17 - Jun 18
The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester
Front of property - evening/night
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1003)
"very hospitable staff"
The price is $168
$185 total
includes taxes & fees
Jun 30 - Jul 1
Hampton Inn and Suites Manchester
Kimpton Taconic Hotel, an IHG Hotel
Exterior
Kimpton Taconic Hotel, an IHG Hotel
4.0 star property
9.4 out of 10, Exceptional, (687)
"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 $179
$236 total
includes taxes & fees
Jun 23 - Jun 24
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.

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 $169 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.

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?

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly: This vacation 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 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?

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

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.

Recent reviews of Rupert properties
Expedia verified reviews

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant

5/5 Excellent
Amazing
"Amazing Stay."
A verified traveler stayed at The Reluctant Panther Inn and Restaurant
Posted 2 days ago
The Reluctant Panther Inn and Restaurant