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Compare 349 Vacation Homes in Rupert with updated reviews, rates, and availability.

Plenty of Room For Everyone! - 5 Minutes to Stratton
9.8 out of 10, Exceptional, (10)
"We had a great time staying here! It was close to the Stratton Mountain Resort to go see the foliage, a few cute cafes nearby for coffee and food, and the house itself was comfortable. Beautiful little porch balcony and functioning grill."
The price is AED 922
AED 3,299 total
includes taxes & fees
11 Nov - 12 Nov
Plenty of Room For Everyone! - 5 Minutes to Stratton
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
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
9.8 out of 10, Exceptional, (67)
"This home is exactly as described online and the photographs are a true refection of the quality. Great space, layout, level of comfort, and extremely well equipped. The amenities offered within the association/village (swimming pool, tennis court, fitness room, games room...) were a bonus. We would definitely stay in this home again."
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
10.0 out of 10, Exceptional, (12)
"This house was great! It was very clean, had lots of bedrooms, and plenty of room for our group of 7 to have a great weekend. The host was super nice and responded quickly to messages. I would note that there are a lot of stairs, both to get into the house and within the house. Probably not a big deal for people who stay for skiing, but good to know if you have older guests or people who have trouble with stairs."
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
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!
Vermont Lake House
10.0 out of 10, Exceptional, (13)
"We couldn't have had a better time! The house was meticulously clean and so pretty, and absolutely loved the long deck looking out on the water. The fire pit was great fun in the evenings and there was lots of outdoor space for enjoying a good time. The hosts were so warm and friendly and responded quickly to any questions. Loved it!"
Vermont Lake House
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (195)
"Everything about our stay was lovely from the setting of the barn to the host to the cozy simplicity. Super clean too. Highly recommend."
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
7.8 out of 10, Good, (41)
"Can't beat the location. We had a great stay."
The price is AED 272
AED 991 total
includes taxes & fees
6 Nov - 7 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (30)
"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."
The price is AED 2,016
AED 4,864 total
includes taxes & fees
24 Nov - 25 Nov
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
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!
Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour
9.8 out of 10, Exceptional, (99)
"Very nice and clean property with a beautiful view from the deck! The fire pit was lovely in the evening and the host supplied ingredients for making s’mores! The sky was completely clear and we enjoyed star gazing while we enjoyed the fire! The host provided quick responses to questions I asked and provided amazingly detailed information about the property, which was very much appreciated. I would definitely recommend the Rye Chalet to others and hope to stay again soon!!! "
Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
9.0 out of 10, Wonderful, (66)
"We loved it and plan to return some day."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
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
Historic Rideout 16m to Okemo Walk to Town
10.0 out of 10, Exceptional, (16)
"Great for families."
Historic Rideout 16m to Okemo Walk to Town
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
Perfect Reunion House w/pool, fireplace & piano. Dogs welcome. Discounted ski tix at Bromley.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/pool, fireplace & piano. Dogs welcome. Discounted ski tix at Bromley.
Secluded 5 bedroom home on 5 acres! <br>3 miles to the heart of Manchester Center
10.0 out of 10, Exceptional, (102)
"This was our 2nd stay and it was as successful as the 1st stay. This property is very clean and the house and amenities are perfect for our large family gathering. The kitchen has everything you need to prepare a family meal! We are already planning our next visit. Our family loves Manchester and this location is perfect!"
Secluded 5 bedroom home on 5 acres! <br>3 miles to the heart of Manchester Center
Londonderry Retreat ~ 3 Mi to Lowell Lake!
10.0 out of 10, Exceptional, (9)
"My partner and I had a lovely time hanging out in the hot tub and traipsing around the area. The house was well kept and well appointed, as well as VERY clean! We brought my dog with us and to be perfectly honest, I would not have known that other animals had resided there! We made sure to leave a tip for the cleaners. We did not have any issues so we did not have a need to contact the property managers. Overall, it was a wonderful time indeed."
Londonderry Retreat ~ 3 Mi to Lowell Lake!
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
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
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!"
The price is AED 1,178
AED 1,459 total
includes taxes & fees
6 Nov - 7 Nov
Long Trail House at Stratton Mountain Resort
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (157)
"This was a beautiful house but we were a little taken aback that it wasn’t situated on the grounds the way the photos showed. There is a neighbor right next door. Please read the details of the booking closely because they definitely did not leave extra toilet paper or paper towels. The towels were not great. I would be aware also that the house is very dark No closet lights and the hallways get very dark just because it is an all wood house. It is a huge house with lots of space and the fit...
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
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.