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Compare 31 Chalets in Rupert with updated reviews, rates, and availability.

Green Mountain Manor - Ski and Summer Chalet
9.8 out of 10, Exceptional, (7)
"Relaxing VT stay . You are in a rural setting but places to stock up on supplies was less then 10 miniutes away . We watched the fireworks that stratton displayed pretty much from the comfort of the property .Our children are young adults and they had a blast finding local swimholes . As well as spending a day at Bromley Mountain ( 20 mins away ) where they did water slides , alpine slides , the giant swing to name a few . House is large and the ability to accomodate large families or groups ....
Green Mountain Manor - Ski and Summer Chalet
Serene & Stylish Chalet w/ HOT TUB near Manchester
10.0 out of 10, Exceptional, (9)
"We were very comfortable and relaxed, just what you want for a vacation. The property was clean and well appointed. We only lacked an outdoor outlet for charging our car. The host was in touch and helpful. We would stay here again."
Serene & Stylish Chalet w/ HOT TUB near Manchester
On Shuttle, 12 min walk to village. Late Check out. Private Baths
9.8 out of 10, Exceptional, (6)
"Great location and comfortable"
On Shuttle, 12 min walk to village. Late Check out. Private Baths
Classic Alpine Vermont Chalet
10.0 out of 10, Exceptional, (8)
"Fit the bill for our group of 8 skiing at Stratton for the weekend. Quirky decor and foosball table were a plus. Easy check in/check out"
Classic Alpine Vermont Chalet
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.
Cozy Creekside Chalet centrally located near 4 ski resorts
10.0 out of 10, Exceptional, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is SAR 934
SAR 2,143 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Creekside Chalet centrally located near 4 ski resorts
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
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
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
The price is SAR 1,024
SAR 3,019 total
includes taxes & fees
25 Sep - 26 Sep
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Brian Piece of Heaven for fall Foliage. Beautiful colors
9.8 out of 10, Exceptional, (26)
"Good place to stay with a well-equipped kitchen. It has a well lived-in feel, as opposed to a spotless modern hotel feel, so don't expect luxury. But it is homey and comfortable. Unfortunately, we had an issue with bees getting inside the apartment, and we had to leave early (I'm allergic). The host is working on resolving the problem. Host is very responsive and easy to work with."
Brian Piece of Heaven for fall Foliage. Beautiful colors
Cozy Chalet on Magic Mountain
10.0 out of 10, Exceptional, (7)
"My wife and I had a great stay at the chalet this past weekend. The property was exactly as described and very well maintained. We would absolutely stay here again!"
Cozy Chalet on Magic Mountain
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
9.2 out of 10, Wonderful, (19)
"As a yearly VRBO renter I am accustom to renting a few houses and this one had some disappointing takes and some great attributes. First the houses layout and location is great for a large get together and the views are amazing! But apon arriving you could first tell the slate entry way and door knob was in need of repair. From there we had a few other dissapointments, the dishes were dirty, scattered about the kitchen. Towels were damp and we later learned why, it was because the dryer simply...
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
Bromley Aframe - King Master Bed, Wood Fireplace
10.0 out of 10, Exceptional, (11)
"Visited for the fall foliage, and Vermonr is absolutely stunning. Bromely house was clean, comfortable and was as advertised. Location was perfect for our stay. Would not hesitate to stay there again."
The price is SAR 689
SAR 1,537 total
includes taxes & fees
7 Oct - 8 Oct
Bromley Aframe - King Master Bed, Wood Fireplace
Charming 5BR Chalet@Base of Stratton Mt Has It All
9.6 out of 10, Exceptional, (9)
"This property is absolutely perfect for a large group staying at Stratton. Plenty of bedrooms / beds / baths, open space around the kitchen and living room areas, plenty of parking and more. Fireplace is great. Hot tub and sauna come in clutch. Location is ideal. Owner communicates great. We were a group of 9 friends up for a quick ski trip. Would definitely book it again."
Charming 5BR Chalet@Base of Stratton Mt Has It All
Mountain Retreat Getaway With Incredible Fall Views
10.0 out of 10, Exceptional, (2)
"We had an awesome stay. So much to do in the area. Accommodations were spotless and communication was great. Loved it. "
Mountain Retreat Getaway With Incredible Fall Views
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
10.0 out of 10, Exceptional, (9)
"Just got back from three nights at this wonderful property with a group of 50-somethings to compete in a gravel bike race. This property was ideally located near our start line, very very clean, plenty of room for us, basically as advertised. Would definitely rent here again in the future given all of the above.."
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Stylish Mountain Getaway close to Stratton w/ Spa
10.0 out of 10, Exceptional, (6)
"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "
Stylish Mountain Getaway close to Stratton w/ Spa
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks
9.6 out of 10, Exceptional, (4)
"We had a great stay here! The host was very informative and pleasant to work with and the house offered a lot of amenities. Lots of beds which is perfect for a big group. Thank you for hosting us!"
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
10.0 out of 10, Exceptional, (5)
"We had a lovely weekend ski trip with friends here and everything was excellent. The house was even more beautiful in person than in the photos. Plenty of room in the driveway for lots of cars, had a tricky time connecting the Bluetooth speaker to the projector but our host Eric was very helpful in talking us through how to connect it. Hot tub was hot and worked great all weekend, I was honestly very impressed with how well it was able to maintain its heat in single digit temperatures outside....
The price is SAR 1,801
SAR 4,919 total
includes taxes & fees
24 Sep - 25 Sep
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
MtSnow/Stratton Chalet w/Hot Tub
10.0 out of 10, Exceptional, (2)
"Went with a group of friends and we all enjoyed the house. The hot tub, pool table and extra living room made it the perfect spot to hang out at night after a long day of hitting the slopes. Sam was very responsive and this might be the cleanest VRBO I’ve stayed in."
MtSnow/Stratton Chalet w/Hot Tub
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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 property types in Rupert

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
3.0 star property
8.4 out of 10, Very Good, (71)
"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.
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.
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.