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Compare 28 Chalets in Rupert with updated reviews, rates, and availability.

Cozy Creekside Chalet centrally located near 4 ski resorts
Autumn view of Forestream

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (8)
"Nice location. Plenty of room for 6 adults. Pellet stove and Christmas movies after a day of shopping and exploring made for a perfect night. "
The price is SAR 1,386
SAR 2,735 total
includes taxes & fees
27 Dec - 28 Dec
Cozy Creekside Chalet centrally located near 4 ski resorts
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
Large 3 FL Chalet

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

10.0 out of 10, Exceptional, (6)
"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....
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Welcome to Skylight Ski Lodge!

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
Aerial view

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (30)
"The house was very cozy and easy to get comfortable. It is surrounded by woods. We were lucky to get a lot of snow one day of our stay so we were literally in a magnificent winter wonderland-a perfect stay!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Serene & Stylish Chalet w/ HOT TUB near Manchester
Book a stay in Winter Wonderland! Relax in the hot tub after a day at the slopes

Serene & Stylish Chalet w/ HOT TUB near Manchester

10.0 out of 10, Exceptional, (11)
"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
Charming 5BR Chalet@Base of Stratton Mt Has It All
Great Rm Living Rm3

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
Stylish Mountain Getaway close to Stratton w/ Spa
Spacious living room

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.
Open Living room

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.
Green Mountain Manor - Ski and Summer Chalet
Aerial view

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

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
Exterior

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
Cozy Chalet on Magic Mountain. Close to Stratton and Bromley.
Property grounds

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

10.0 out of 10, Exceptional, (8)
"Great place ! Very clean, close to attractions and communication with owner was great ! Can’t wait to come back. "
Cozy Chalet on Magic Mountain. Close to Stratton and Bromley.
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton
Updated and fully stocked kitchen

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
On Shuttle, 12 min walk to village. King Beds with Private Baths
Exterior

On Shuttle, 12 min walk to village. King Beds with Private Baths

9.8 out of 10, Exceptional, (7)
"Great location and comfortable"
On Shuttle, 12 min walk to village. King Beds with Private Baths
Bromley Aframe - King Master Bed, Wood Fireplace
Front of house - leaves changing in October peeping season

Bromley Aframe - King Master Bed, Wood Fireplace

9.8 out of 10, Exceptional, (12)
"The property and house are truly beautiful. Great for a family stay. Fall foliage views are beautiful. The owner responded to all of my messages in a timely fashion. Located only two minutes away from Bromley which was great. There was a ceiling leak in the hallway while we were there but it wasn't bad. It was just the two of staying for one night and I do feel that charging the full cleaning fee for the one night for just the two of us was a bit high/overpriced. It would be nice if it could...
Bromley Aframe - King Master Bed, Wood Fireplace
Cozy Chalet in Vermont's Golden Triangle
Dining

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
Classic Alpine Vermont Chalet
Exterior

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"We loved everything about this property. Lots of bedrooms, comfortable beds, big living room and kitchen area and very close to the downtown area. I highly recommend this house for large families looking for a place to stay in Vermont!"
Classic Alpine Vermont Chalet
Stratton-View Ski Retreat 10 Min to Stratton | Hot Tub
Today is the perfect bluebird day for skiing. Hit the slopes just moments away from our doorstep.

Stratton-View Ski Retreat 10 Min to Stratton | Hot Tub

10.0 out of 10, Exceptional, (3)
"Fantastic location, scenery and chalet. Everything was amazing. Our hosts were attentive friendly and welcoming. We really appreciate that, especially now when customer service seems to be declining. "
Stratton-View Ski Retreat 10 Min to Stratton | Hot Tub
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Interior

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!
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks
Nestled in the trees yet walkable to Magic's bars, restaurants, and hiking.

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
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
Exterior

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (159)
"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Long Trail House at Stratton Mountain Resort
Living room

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 1,424
SAR 1,770 total
includes taxes & fees
6 Jan - 7 January 2025
Long Trail House at Stratton Mountain Resort
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Active Tinmouth cabin in the eve!

Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.

10.0 out of 10, Exceptional, (160)
"Wonderful property, gracious hosts, zero complaints"
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.