Rupert Holiday Rentals

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Holiday 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, (156)
"Came for four day stay because of my daughter and her new husband‘s wedding… At the old Gray barn… My brother and nephew and I shared the Creekside cabin… Beautiful rustic cabin with all the amenities one could want… I can see now why they picked the spot to get Married… It is a beautiful location in Dorset… Finding the Creekside cabin was a great find my brother said he owes me for years to come now lol dan’s place is spectacular"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Long Trail House at Stratton Mountain Resort
Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (72)
"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!"
Long Trail House at Stratton Mountain Resort
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, (156)
"We had a wonderful trip and stay at the cabin. The owners were so helpful and great communication. They went above and beyond to make sure our stay was great!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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, (188)
"Beautiful little cottage hidden in the woods, everything you could need was provided The kitchen was fully equiped, cozy comfortable living room area spacious bathroom with huge tub and the most comfortable bed we’ve ever slept in Defiantly coming back Thank you "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
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
Summit Views - Stratton-Manchester Mountain and Golf Retreat w/Hot Tub and Sauna
Property grounds
Summit Views - Stratton-Manchester Mountain and Golf Retreat w/Hot Tub and Sauna
10.0 out of 10, Exceptional, (57)
"We had a wonderful stay in Vermont. The house was great with a gorgeous view! We enjoyed campfires every night and Jason was a very pleasant host."
Summit Views - Stratton-Manchester Mountain and Golf Retreat w/Hot Tub and Sauna
VT Cabin overlooking the West River and Village
Fridge, oven, stovetop, dishwasher
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (24)
"Everything was exactly as we needed at this location. Plenty of amenities less than a 5 minute drive away and everything you could need is in the unit. Easy check in/out and very responsive. Lots of entertainment options too."
The price is HK$1,550
HK$3,063 total
includes taxes & fees
24 Sept - 25 Sept
VT Cabin overlooking the West River and Village
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Exterior
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
10.0 out of 10, Exceptional, (36)
"We absolutely love this property and always look forward to coming there, so beautiful there. Love the location and it has anything you might need. "
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Property grounds
Shuttle or walk to village and lifts! The Powder Haus Chalet!
10.0 out of 10, Exceptional, (31)
"Our group of 8 found the property to be a perfect accomodation while staying in town for a wedding. Check in was very convenient and communication with the host was excellent. The home was very spacious, the living area was a great space to hang out and spend time together. We had all the amenities we needed for an easy weekend while attending a friend's wedding. The location is excellent and was very convenient to the mountain. We are especially grateful for the host allowing our furry friends...
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Vermont Lake House
Fridge, microwave, oven, stovetop
Vermont Lake House
10.0 out of 10, Exceptional, (12)
"We had a fantastic long weekend stay. House was very well equipped for two different families to stay. Plenty of space for kids and adults to empty different activities. Water access is great and we all loved the boats. Hosts were very communicative and kind. "
Vermont Lake House
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
8.6 out of 10, Excellent, (7)
"Really enjoyed staying there. The farm was wonderful, quite and made wonderful memories with my granddaughter."
Nature Retreat, Pet Friendly Cozy Cabin On 80 Acres With Fields & Forrest Trails
Long Trail House Studio at Stratton Mountain Resort
Exterior
Long Trail House Studio at Stratton Mountain Resort
10.0 out of 10, Exceptional, (55)
"Perfect "
Long Trail House Studio at Stratton Mountain Resort
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, (42)
"Blue Door Farm is a great house, we loved the little pub in the basement. Everything you need to let your family enjoy quaint, quiet, quality time together. Don't miss Taylor Farms if you have little ones or Mike and Tammy's fried chicken any time or the donuts on Sunday, maple are the best."
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Adirondack Lake home w private dock
Outdoor dining
Adirondack Lake home w private dock
10.0 out of 10, Exceptional, (13)
"Our group had a lovely week on Tupper Lane! The best part was that we were able to bring our dogs with us. We’ve never seen them so happy! The house was beautiful and clean. And we really enjoyed the fire pit and screened in porch. Karen was so easy to communicate with. I would definitely recommend this place!"
Adirondack Lake home w private dock
Home with a spring-fed pond and mountain view.
Pool
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (106)
"Beautiful and peaceful setting. Owner was next door and very friendly, welcoming and non-intrusive. I hope to go back sometime soon!"
Home with a spring-fed pond and mountain view.
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, (27)
"We really enjoyed our stay at this house. All the rooms were beautiful, clean and nicely decorated. The beds were very comfortable. Our dog loved the porch on the main floor. We will definitely book this house again, it is one of our favorites."
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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, (251)
"Rik was a great host. Teri was delightful. The listings need to be clarified (AC and tv). Pictures need updating."
Private and Artistic cabin, Pet friendly, no cleaning fee
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, (194)
"The place was beautiful and immaculate "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"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.
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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.
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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, (410)
"We loved the property and the staff was excellent. "
The price is HK$2,175
HK$2,822 total
includes taxes & fees
30 Sept - 1 Oct
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, (1006)
"The staff was excellent. They were very friendly, helpful, and accommodating. "
The price is HK$1,443
HK$1,587 total
includes taxes & fees
23 Oct - 24 Oct
Hampton Inn and Suites Manchester
The Black Bear Lodge at Stratton Mountain Resort
10 restaurants, lunch, dinner served; American cuisine
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.4 out of 10, Good, (848)
"Liked your staff. Very helpful "
The price is HK$951
HK$1,151 total
includes taxes & fees
24 Sept - 25 Sept
The Black Bear Lodge at Stratton Mountain Resort
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.

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 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 Equinox Preservation Trust and Southern Vermont Arts Center.

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.