Rupert Vacation Rentals

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Vacation Rentals in Rupert

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}
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
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, (68)
"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 $321
$389 total
includes taxes & fees
May 27 - May 28
Long Trail House at Stratton Mountain Resort
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Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (143)
"Beautiful/nicely appointed home. The house had everything in it to make for a very comfortable stay and the hosts were so gracious, helpful, and communicative. We didn't want to leave and already can't wait to make a return trip! Thanks, Angelo and Deb!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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
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!"
The price is $476
$787 total
includes taxes & fees
May 20 - May 21
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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
Pool
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (101)
"We had a great stay with our pup for a late ski season weekend! The house was clean, well-stocked, and very cozy. The location was beautiful and perfectly situated a few minutes away from everything you could want to do in Manchester. We will definitely be back!"
Home with a spring-fed pond and mountain view.
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
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.
Fridge, microwave, oven, stovetop
Vermont Lake House
10.0 out of 10, Exceptional, (6)
"The house was clean and full of extras such as a multi function game table, shelves of assorted boxed games & cards. There was a large deck with a large BBQ. All the rooms a large family would need. Clean and functional kitchen. A responsive owner that was immediately available for any questions. The view of the lake was delightful. If you find yourself in the Poultney VT. vicinity, this is the place to stay."
Vermont Lake House
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 $165
$340 total
includes taxes & fees
May 20 - May 21
VT Cabin overlooking the West River and Village
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
Exterior
Cabin in So. Vt Spring deals 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 Spring deals enjoy the Mtns.
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
Indoor pool, a heated pool
Hike, Explore, Swim ~ Adventure in Vermont!
9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Hike, Explore, Swim ~ Adventure in Vermont!
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
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 $74
$286 total
includes taxes & fees
May 19 - May 20
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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.

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

Front of property - evening/night
Hampton Inn and Suites Manchester
2.5 star property
9.6 out of 10, Exceptional, (1000)
"Excellent customer service, newer facility, smells clean. I wish the room windows opened for some fresh air "
The price is $161
$177 total
includes taxes & fees
May 23 - May 24
Hampton Inn and Suites Manchester
Exterior
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (351)
"No thanks"
The price is $139
$202 total
includes taxes & fees
Jun 9 - Jun 10
The Equinox Golf Resort & Spa
Exterior
Kimpton Taconic Hotel, an IHG Hotel
4.0 star property
9.4 out of 10, Exceptional, (680)
"From the moment you walk in you are greeted by a friendly staff who make it clear that you having a good time is their primary purpose. I just had to ask and a microwave was provided for our room. The rooms are bright and comfortable, and each closet comes with a walking stick for hiking on the fabulous trails in the area, a yoga mat and bath towels. Such a treat!"
The price is $188
$245 total
includes taxes & fees
May 27 - May 28
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 $74 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 Manchester View

The Manchester View

5/5 Excellent
Tranquil and beautiful!
"It was cozy and charming! Great views and wonderful hospitality! "
A verified traveler stayed at The Manchester View
Posted 2 days ago
The Manchester View