Search Chalets in Rupert

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 41 Chalets in Rupert with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (51)
"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

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (9)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AED 559
AED 1,642 total
includes taxes & fees
14 Jun - 15 Jun
Cozy Creekside Chalet centrally located near 4 ski resorts

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

10.0 out of 10, Exceptional, (107)
"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

The MountainTop

10.0 out of 10, Exceptional, (1)
"Nick’s cabin was perfect. Beautifully built and decorated, the cabin was amazing. Nick’s place had everything we needed and more. The location was tucked away with beautiful surroundings and close to Stratton mountain. Nick was always quick to reply with any questions and made sure our stay was perfect. Only regret is we didn’t stay here longer! "
The MountainTop

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"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

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.2 out of 10, Wonderful, (7)
"Nice hill for sledding. Missed having electric mixer for potatoes. Nice community area of kitchen, dining room and living room. Good setup of rooms. "
The price is AED 793
AED 1,947 total
includes taxes & fees
9 Jun - 10 Jun
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, (35)
"Stayed 3 nights everything was spotless & so very comfortable. This was our 2nd stay here. The host is always reachable & prompt to respond. Can’t wait to hopefully stay here again. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub

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

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
Green Mountain Manor - Ski and Summer Chalet

Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK

10.0 out of 10, Exceptional, (9)
"A wonderful and spacious house that is perfect for large groups. The house was well stocked, host was responsive and helpful, and the hot tub was great! Would definitely stay here again. "
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK

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

9.8 out of 10, Exceptional, (15)
"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 1,869
AED 3,553 total
includes taxes & fees
6 Jul - 7 Jul
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

Classic Stratton Ski Chalet: Perfect for Families

10.0 out of 10, Exceptional, (1)
"Enjoyed our three night stay here. The kitchen is well stocked with pots and pans, dinnerware, silverware, utensils, etc. Beds were very comfortable. Our only disappointment was that we couldn't have a fire in the fireplace as the chimney was in need of repairs. Hope to be back next year."
Classic Stratton Ski Chalet: Perfect for Families

Two Bedroom Chalet, Charming, Quiet, River Front

9.4 out of 10, Exceptional, (74)
"Loved the location and the house was great. All amenities were as described. Great host. Highly recommend. "
Two Bedroom Chalet, Charming, Quiet, River Front

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

10.0 out of 10, Exceptional, (10)
"We had a wonderful time and enjoyed our stay at your home! Great space and the kids loved playing downstairs and sleeping in the bunk room!"
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"Easiest vrbo experience we’ve had to date."
Classic Alpine Vermont Chalet

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

9.2 out of 10, Wonderful, (12)
"We totally enjoyed our stay. The home was magnificent. Close to everything, ski lifts, restaurants, etc. Definitely recommend to future guests. We are booking again next year."
Charming 5BR Chalet@Base of Stratton Mt Has It All

Serene & Stylish Chalet ~HOT TUB ~ near Manchester ~ Pet-friendly

10.0 out of 10, Exceptional, (13)
"Cozy and warm. It was a nice get away for me and my girlfriend I would visit again. "
Serene & Stylish Chalet ~HOT TUB ~ near Manchester ~ Pet-friendly

Stylish Farmhouse - Close to Ski, Golf + Hot Tub

10.0 out of 10, Exceptional, (6)
"We really loved this house! thank you so much for sharing it with us!"
The price is AED 661
AED 2,192 total
includes taxes & fees
9 Jun - 10 Jun
Stylish Farmhouse - Close to Ski, Golf + Hot Tub

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

9.8 out of 10, Exceptional, (59)
"We stayed along with 2 other families while in time visiting Okemo mountain. The house was very welcoming, clean and exactly how the picture showed it. We would stay here again next time we were in time. "
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni
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.
Save an average of 15% on thousands of hotels when you're signed in