Rupert Vacation Rentals from CA $153: Short-Term Rentals for 2025

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Vacation Rentals in Rupert

"We felt welcomed from the moment we walked in (with our dog) until we left. The home was clean, instructions were clearly posted, a few overnight inches of snow were promptly cleared, and the host was responsive. Dorset Vt. is a nice small town as well. We recommend this rental and hope to return some day."

"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "

CA $677 total

includes taxes & fees

Jan 27 - Jan 28

"Spacious, comfortable and had everything we could have wanted for a holiday ski vacation. The weather wasn't entirely cooperative as far as the skiing, but we didn't mind with such a lovely place to settle in for a couple of cozy and relaxing winter days. "

"… And it remains a gem! We lucked out w/a foot of snow on Thanksgiving and so kept the fires burning. Just a great, special place."

"We had a great time. 6 mikes from Bromley Mtn. Scott was excellent w thorough & timely communication. Great location, spacious, very clean. Has a full kitchen, nice log cabin feel. Very quaint. We will be staying here again. Thank you for a wonderful getaway "

CA $502 total

includes taxes & fees

Jan 15 - Jan 16

9 bedrooms, desk, iron/ironing board, free WiFi

"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...

"Wonderful stay. Thanks again"

CA $464 total

includes taxes & fees

Jan 16 - Jan 17

"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."

CA $1,631 total

includes taxes & fees

Jan 20 - Jan 21

"This trip was just as wonderful as the first. Spent our second Thanksgiving in this beautiful and private setting. It snowed 13 inches on TG day and it was so gorgeous! Sitting in the hot tub with the snow falling was really perfect. Everything was provided and check in and checkout were easy. Located close to Manchester, we had fun trying out hand at glass blowing at Hot Glass..too fun! Would recommend this place to all."

"We have stayed here multiple times and enjoy every one!"

"This place was built for a family gathering! Everyone had a private bath and a suite. No waiting for a shower here. The tavern was fun and allowed the group to come together. The outdoor fire pit was a hit too. We will be back. "

Smart TV, fireplace, video games, Netflix

"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."

"Muy linda, hogareña, ideal para todos. Si lo que buscas es traquilidad y salir del la rutina de la ciudad, esto es perfecgo para ti... "

"Great location"

"The condo was clean. The village so pretty walking through in the snow. Second time we rented the same co do. All good. "

"This is the first VRBO that actually exceeded my expectations. It was the perfect place for a relaxing, stress free Vacation. "

"Location was fantastic. Near shops, stores, restaurants and lifts. Room condition was somewhat dated and worn but livable. Also next to large parking lot which was cleaned daily by noisey trucks at 4am! Felt like "My Cousin Vinny""

CA $711 total

includes taxes & fees

Jan 30 - Jan 31

"Really enjoyed staying there. The farm was wonderful, quite and made wonderful memories with my granddaughter."

"Family trip for Christmas in this fantastic house! The indoor pool was so clean and warm, with plenty of fun pool toys and floats. Everything you need for a family is in this house- from video games and board games to pool towels and throw blankets. There were tons of movies, a super warm pellet stove in the main living room, upgraded appliances, luxury bedding,& a great snow shovel which came in handy.Such great communication with house manager. Overall, much better than expected. Location is...

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Other types of properties in Rupert you may be interested in

"Very friendly , great family spot"

CA $250 total

includes taxes & fees

Jan 20 - Jan 21

"We loved our short stay at the Taconic, it's now our new favorite place for a quick getaway. The service was excellent. Our room was comfortable, very clean and had the sweetest fireplace. Looking forward to our next stay!"

CA $289 total

includes taxes & fees

Jan 27 - Jan 28

"Service was great as always. Thanks for the EV charging, which is the primary reason we continue going there. Thanks Katey for great service."

CA $228 total

includes taxes & fees

Jan 20 - Jan 21

Find out more about Rupert

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rupert vacation rentals we have selected for you start as low as CA $153 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 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.

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.)

Recent reviews of Rupert properties

5/5 Excellent

Great hotel for EVs

"Service was great as always. Thanks for the EV charging, which is the primary reason we continue going there. Thanks Katey for great service."

A verified traveller stayed at Hampton Inn and Suites Manchester

Posted 10 hours ago

5/5 Excellent

Cannot wait to go back!

"We loved our short stay at the Taconic, it's now our new favorite place for a quick getaway. The service was excellent. Our room was comfortable, very clean and had the sweetest fireplace. Looking forward to our next stay!"

A verified traveller stayed at Kimpton Taconic Hotel, an IHG Hotel

Posted 8 days ago

5/5 Excellent

"We enjoyed the large rooms, comfortable beds, ease of parking compared to other properties in the area, and the deck off the back of the room. There are no amenities (food, shampoo, conditioner) but this hotel is a very good value for the price and I'd highly recommend it to travelers on a budget."

A verified traveller from Boston stayed at Weathervane Motel

Posted 10 days ago

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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?

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton: This vacation home rental outside of Rupert is located on a lake and has a balcony, a spa tub, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

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?

Green Mountain National Forest and Merck Forest Farmland Center are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Stratton Mountain Resort 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.

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Rupert Vacation Rentals

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Check prices for these dates

Vacation Rentals in Rupert

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

VT Cabin overlooking the West River and Village

VT Cabin overlooking the West River and Village

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

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!

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Vermont Lake House

Vermont Lake House

Cabin in So. Vt enjoy the Mtns.

Cabin in So. Vt enjoy the Mtns.

Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

ADK Lakehouse with private dock

ADK Lakehouse with private dock

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails

Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

Other types of properties in Rupert you may be interested in

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

Find out more about Rupert

Find out more about Rupert

Rupert Vacation Rental Travel Info

Recent reviews of Rupert properties

Recent reviews of Rupert properties

Hampton Inn and Suites Manchester

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions