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Compare 30 Chalets in Rupert with updated reviews, rates, and availability.

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

10.0 out of 10, Exceptional, (2)
"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

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (31)
"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

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

9.6 out of 10, Exceptional, (10)
"Our multi-generational group had a wonderful stay at this perfect ski house! The house is well represented by the listing photos. It’s clean, spacious, and had everything we needed. I had several questions for the owner before and during our stay. His responses were timely and helpful. We would love to stay here again! "
Charming 5BR Chalet@Base of Stratton Mt Has It All

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!

Cozy Chalet on Magic Mountain. Close to Stratton, Bromley and Okemo.

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 Chalet on Magic Mountain. Close to Stratton, Bromley and Okemo.

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

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

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 SAR 934
SAR 2,184 total
includes taxes & fees
3 Mar - 4 Mar
Cozy Creekside Chalet centrally located near 4 ski resorts

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

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

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

9.6 out of 10, Exceptional, (45)
"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.

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...
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, (29)
"The place was adorable , very clean , view was pretty and Brian the host was very friendly and accommodating. Loved it!"
Brian Piece of Heaven for fall Foliage. Beautiful colors

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

10.0 out of 10, Exceptional, (5)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
The price is SAR 1,253
SAR 2,755 total
includes taxes & fees
18 Mar - 19 Mar
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Serene & Stylish Chalet w/ HOT TUB near Manchester and Skiing

10.0 out of 10, Exceptional, (12)
"Cozy and warm. It was a nice get away for me and my girlfriend I would visit again. "
Serene & Stylish Chalet w/ HOT TUB near Manchester and Skiing

Perfect house surrounded by National Forest to get away and decompress!!!

10.0 out of 10, Exceptional, (2)
"Comfortable house. Gas fireplace. Had everything we needed. Communication was fast and easy. Would stay here again for a family ski trip. "
Perfect house surrounded by National Forest to get away and decompress!!!

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

9.8 out of 10, Exceptional, (9)
"It’s a great house for multiple families. We had kids aged 5-13 - 2 families and we enjoyed the space. Close to Stratton and on the shuttles path which was super helpful. Has a great dining area where everyone could fit.Very clean and well maintained. "
The price is SAR 3,747
SAR 6,048 total
includes taxes & fees
22 Feb - 23 Feb
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

Cozy Chalet in Vermont's Golden Triangle

8.8 out of 10, Excellent, (5)
"We enjoyed our stay during the holiday week. The fenced in yard for our pups was definitely a plus and hard to find in a rental. Just a note of caution regarding the stairs in the home. They are very steep, and we had an elderly family member with us. Luckily there is a first-floor bedroom and bathroom, so all worked out fine. The owners were very responsive to any questions we had. Is a lovely spot and would recommend it to others. "
Cozy Chalet in Vermont's Golden Triangle

Now booking Stratton for MLK and February break.

10.0 out of 10, Exceptional, (1)
"Great location, private, well-stocked kitchen (we cooked in every night!) and short drive to Stratton. Clean, comfortable and with great light. Would recommend others to stay (of note, loft is not for small or young children).Host is quickly responsive with the few questions we had.Thank you for sharing your home with us! Would return!! "
Now booking Stratton for MLK and February break.

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
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

Gorgeous Victorian-Style House w/ Hilltop Pool!

8.8 out of 10, Excellent, (29)
"The house was a perfect weekend getaway for a group of friends from the city. It was absolutely gorgeous and had everything we could need. We even got two feet of snow, so it was a magical Vermont experience! We would definitely go back and thank you!"
Gorgeous Victorian-Style House w/ Hilltop Pool!

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is SAR 1,556
SAR 1,934 total
includes taxes & fees
3 Mar - 4 Mar
Long Trail House at Stratton Mountain Resort

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

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
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.