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Compare 339 Vacation Homes in Rupert with updated reviews, rates, and availability.

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

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

Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

10.0 out of 10, Exceptional, (43)
"Brad was a wonderful host and the home and area had so much for us to do. It was the perfect place to get away and be with friends. "
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

10.0 out of 10, Exceptional, (64)
"We had several events during our son's wedding weekend. The house and barn made for a great landing spot between events. We had plenty of room for all of our family. The property was very large and allowed for several sitting areas, both inside and outside. The landscape around the house made a great backdrop for pictures for the groom and groomsmen. The house has everything you need. "
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

9.0 out of 10, Wonderful, (4)
"Very Clean, roomy, nicely laid out, close to ski areas. Owner was responsive and available. All went very well. I would recommended this without reservation."
Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

10.0 out of 10, Exceptional, (22)
"GREAT TIME ! GREAT HOUSE"
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Family oriented community in country setting...10 minute walk to town center.

10.0 out of 10, Exceptional, (19)
"The property was really perfect. In perfect condition. Spotlessly clean. Nice views of the mountains. Great location for access to amenities."
Family oriented community in country setting...10 minute walk to town center.

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

10.0 out of 10, Exceptional, (3)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome

10.0 out of 10, Exceptional, (55)
"The house is beautiful & has tons of nooks and crannies. Fun for exploring!"
HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome

Magnificent Vermont home w/free WiFi, full kitchen, firepit, patio, & deck

9.8 out of 10, Exceptional, (33)
"Lots of space to spread out. Kitchen was well appointed. Location was less than 10 minutes to Manchester. "
Magnificent Vermont home w/free WiFi, full kitchen, firepit, patio, & deck

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

10.0 out of 10, Exceptional, (158)
"A beautiful home in a beautiful setting, off the beaten track but not that far from many delightful areas. Kept immaculately clean, every aspect of this property is comfortable, cozy, and welcoming. Communication with the owners is easy and efficient, with response received very quickly."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Historic 6-BR Across From Equinox Resort

9.6 out of 10, Exceptional, (4)
"Great house in a perfect location, we really enjoyed our stay for a family vacation!"
Historic 6-BR Across From Equinox Resort

Manchester Center Home w/ Green Mtn Views!

9.6 out of 10, Exceptional, (30)
"Really enjoyed the quiet privacy and the collection of small wood carvings and glass pieces throughout the house. Good wi-fi, too! The area around Manchester was lovely for exploring. "
Manchester Center Home w/ Green Mtn Views!

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (18)
"Everything about this house was great! We will definitely be back!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Sunny Stratton Townhome ~ 1 Mi to Skiing!

10.0 out of 10, Exceptional, (4)
"Wonderful and clean townhome! Perfect location to be close to Stratton Resort. Thank you!"
Sunny Stratton Townhome ~ 1 Mi to Skiing!

Getaway @ Vermont 4214

9.4 out of 10, Exceptional, (3)
"This place is beautiful. Gorgeous property, clean home, everything you need they have it including all the information of the surrounding area. A list of restaurants, shops, trails, entertainment. The host was awesome. Will be staying again. "
Getaway @ Vermont 4214

Three Bedroom home with loft

Three Bedroom home with loft

Spacious Family getaway near Magic Mountain, VT

9.4 out of 10, Exceptional, (3)
"Perfect house for family with kids ! Plenty of room for three families !"
Spacious Family getaway near Magic Mountain, VT

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
9.8 out of 10, Exceptional, (10)
"Alex was great! We had a great weekend getaway. Thanks for the firewood!"
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
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 property types in Rupert

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

10.0 out of 10, Exceptional, (158)
"A beautiful home in a beautiful setting, off the beaten track but not that far from many delightful areas. Kept immaculately clean, every aspect of this property is comfortable, cozy, and welcoming. Communication with the owners is easy and efficient, with response received very quickly."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

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

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

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
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.