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Compare 39 Chalets in Rupert with updated reviews, rates, and availability.

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 AED 1,477
AED 3,553 total
includes taxes & fees
31 Mar - 1 Apr
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (32)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (106)
"What a great escape. Plenty of space for plenty of folks, beautifully designed. Dining room table is gorgeous. Hosts were quick to respond throughout the process, would come back."
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

8.8 out of 10, Excellent, (3)
"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "
Mid-Century Arty Chalet - 2 Min to Stratton Slopes

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (9)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is AED 841
AED 2,053 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts

Charming 5BR Chalet@Base of Stratton Mt Has It All

9.6 out of 10, Exceptional, (11)
"Our trip this past weekend to Chalet O'Bear was just what we wanted! Booking and communication with the property manager was seamless. Any issues we had were addressed immediately and taken care of. We loved the location of the property and made our stay at Stratton perfect! We will be looking to book again! "
Charming 5BR Chalet@Base of Stratton Mt Has It All

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"The house was just what we needed for a family wedding in Manchester. Quite literally right off the highway but the house itself is nestled back and quiet so you don’t even hear the road. "
Classic Alpine Vermont Chalet

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"Overall, a very good stay. The house is a bit smaller than we thought, but it was very clean and well stocked. The indoor fireplace and provided wood was a nice perk. The hot tub was not clean or well kept, so beware of that. There were body hairs and a brown scum ring around the edge."
Stylish Mountain Getaway close to Stratton w/ Spa

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

9.6 out of 10, Exceptional, (45)
"This is a beautiful property that is convenient to town. The only problem with this property is that there is a long term rental below this property that has a fairly large number of tenants who are at best inconsiderate, and at worst deliberately noisy. Expect doors being slammed hard enough to shake the entire unit at 3 AM and people arguing throughout the night. That is on a good night. If you can sleep through that noise this is the place for you. "
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (50)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

Brian Piece of Heaven for fall Foliage. Beautiful colors

9.8 out of 10, Exceptional, (30)
"Perfect spot to getaway for a weekend trip"
Brian Piece of Heaven for fall Foliage. Beautiful colors

Cozy Springtime Retreat on Magic Mountain

10.0 out of 10, Exceptional, (11)
"From the excellent communication and problem solving of our hosts to the fabulous location and completely comfortable accommodations, our stay was perfect. Would absolutely stay here again. "
Cozy Springtime Retreat on Magic Mountain

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

Two Bedroom Chalet, Charming, Quiet, River Front

9.4 out of 10, Exceptional, (74)
"Cindy was a pleasure to work with! Her home was exactly as described. We felt very comfortable in her home and the town of Jamaica is so cute! We went to the cutest little general store every morning to get breakfast and lunch. There are plenty of board games to enjoy waiting for you as you arrive… it is 15 minutes from Stratton Mountain. There is a foyer to leave your boots and jackets to hang. "
Two Bedroom Chalet, Charming, Quiet, River Front

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

9.8 out of 10, Exceptional, (58)
"Property was just as desribed in listing, clean, spacious and great for mulitple families and large groups. Julie was very resposive and accomodating to our every request. Heat and hot water was more than adequate even in below freezeing tempratures, although some extra blankets would have been appreciated.Property is very secluded, no cellular service as soon as you turn off the main roads - make sure GPS is set in advance. AWD vehicle is highly recommended during winter months.Would definitly...
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

10.0 out of 10, Exceptional, (10)
"We had a fantastic stay at this rental! The home was spotless and well-maintained, making it a comfortable and relaxing getaway. It’s conveniently located in the Stratton Mountain area and just a 20-minute drive from Bromley Mountain, making it a great spot for skiing and winter activities.Our kids loved playing in the snow and especially enjoyed the hot tub after a day outside. The kitchen was fully stocked with everything we needed, making meal prep easy. One of the highlights was the real...
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

10.0 out of 10, Exceptional, (13)
"This house was a great spot for 6 adults (parents & grandparents) and 4 kids (7-10 yrs). The upstairs living space worked very well and the kids enjoyed their space downstairs with the Pac-Man game and pool table. Location made it easy to get to the slopes. We had a terrific time and would love to return."
The price is AED 1,888
AED 3,623 total
includes taxes & fees
24 Mar - 25 Mar
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

Chalet 7 minutes to Ski Stratton, Woodstove, Starry Skies, FirePit, View, DogsOK

2.0 star property
6.0 out of 10, (1)
Chalet 7 minutes to Ski Stratton, Woodstove, Starry Skies, FirePit, View, DogsOK

Cozy Chalet in Vermont's Golden Triangle

9.2 out of 10, Wonderful, (7)
"Family of five (kids 4, 8, 11) pup here for skiing at Magic Mountain. Great location, 5 min to mountain and less to a grocery store in the other direction. House was well-quipped but also not overflowing with leftover food or items from previous guests. The basement was a perfect place to put the kids and they loved the foosball table. The fenced in yard was a plus though the snow was high enough that it didn’t actually contain our dog, something other dog owners might want to keep in mind for...
Cozy Chalet in Vermont's Golden Triangle

4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton

9.0 out of 10, Wonderful, (20)
"The only problem I had was with the heat Issue with check in but was resolved in satisfactory time "
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
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, (164)
"Long weekend with friends and our beloved old dog. We were anxious to get back to Vermont and this home was just what we needed. Close to the activities we like, cross country skiing, great book store, cute shops. Accommodations were above what we expected. Dan could not be a better host. We will be back!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort

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

9.6 out of 10, Exceptional, (211)
"Very cute cabin with fireplace and jacuzzi. Host provided firewood - which was a nice touch. Cabin is on dead end private road so, as mentioned, very peaceful. Lots of snow so no deck access, but imagine it would be great in summer too."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.