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Compare 21 Chalets in Charlestown with updated reviews, rates, and availability.

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
10.0 out of 10, Exceptional, (33)
"The home was well appointed with all the amenities and plenty of room for our three families (6 adults and 6 kids). The game room downstairs and open concept living room were awesome and would have been used more often had the weather not been so perfect. The property is truly the star of this place, picturesque mountain views and an amazing fire pit. We will definitely be renting again."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Okemo Mountain Chalet W/ Hot Tub and Game Room
A view of the house looking up the driveway after some early season snow.
Okemo Mountain Chalet W/ Hot Tub and Game Room
9.8 out of 10, Exceptional, (157)
"This chalet was the perfect retreat for our Vermont getaway! The house is beautifully designed, incredibly relaxing, and comes fully equipped with all the essentials for a comfortable stay. We especially enjoyed the cozy fireplace. We stayed in the king bedroom on the top floor, and the new mattress made for an exceptionally comfortable sleep. The chalet served as our home base for a 4-night stay, allowing us to explore different areas of Vermont with easy day trips. Ludlow itself offers plenty...
Okemo Mountain Chalet W/ Hot Tub and Game Room
Mountain chalet
Property grounds
Mountain chalet
10.0 out of 10, Exceptional, (38)
"This is our third year staying at this mountain chalet and we will continue to return in the future! The cleanliness, comforts and location are nothing short of perfect! Thank you for making this beautiful home available for rental. Looking forward to next year!!"
Mountain chalet
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Enjoy a nice fire while you overlook the Sachem Trail and watch people ski by.
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
10.0 out of 10, Exceptional, (17)
"Stay was perfect"
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
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, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is SAR 939
SAR 2,150 total
includes taxes & fees
29 Nov 2024 - 30 Nov 2024
Cozy Creekside Chalet centrally located near 4 ski resorts
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.
Swiss Chalet Family Retreat w/ lake access
Room
Swiss Chalet Family Retreat w/ lake access
Swiss Chalet Family Retreat w/ lake access
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
Okemo 6 Bedroom Chalet.
View of house from top of driveway. Dec. 18th, 2020
Okemo 6 Bedroom Chalet.
9.4 out of 10, Exceptional, (21)
"House was beautiful, cozy, and clean. We had an issue with the hot tub on the first night with it being cold, but they had someone come out the next morning to get it back running and we were able to use it the second night. House is in a great location. No complaints. Would stay here again."
Okemo 6 Bedroom Chalet.
LUXE Forest Retreat
Exterior
LUXE Forest Retreat
The price is SAR 1,138
SAR 1,809 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
LUXE Forest Retreat
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Exterior
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
9.6 out of 10, Exceptional, (30)
"Great location! House had everything we needed. Property owner very flexible. Would definitely rent again!"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
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
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Exterior
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
10.0 out of 10, Exceptional, (10)
"The house is beautiful and we enjoyed our stay! Just need a full length mirror in a bedroom otherwise perfect ski property!"
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Ski Okemo, Killington, Magic & Bromley
Exterior
Ski Okemo, Killington, Magic & Bromley
10.0 out of 10, Exceptional, (9)
"My adult children and I spent Labor Day weekend working on a building project in Chester. This home was just what we needed -convenient location, 4 bedrooms set up for couples, a very serviceable kitchen (we prefer to cook for each other), solid WiFi, and a private restful outdoor space. We would definitely stay there again!"
Ski Okemo, Killington, Magic & Bromley
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Living area
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
10.0 out of 10, Exceptional, (3)
"Roshanak was an excellent host and the place is beautiful. We love the location and its proximity to Okemo and the town. The property is gorgeous, we would book again."
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Cozy Chalet on Magic Mountain
Outdoor dining
Cozy Chalet on Magic Mountain
Cozy Chalet on Magic Mountain
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Welcome to private living in Chester, VT located on 2 acres surrounded by woods
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!
A 65" Samsung Flat Screen TV, Pool Table, Bar, Arcade & Full Bathroom!
Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!
10.0 out of 10, Exceptional, (7)
"This property is awesome. The owners kept us well informed of what our state would be like from the booking of our trip. The view was beautiful and the house was extremely well-maintained. There was enough room for several of us to hang out and most importantly comfortably sleep. They provided us with plenty of games for the kids as well as for us adults I will definitely be booking this property again"
Brand new hot tub, spacious Chalet 1 min from Okemo base and Ludlow Downtown!
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 Charlestown

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
Spacious, private lot
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
9.8 out of 10, Exceptional, (163)
"Stayed at this property with 11 co-workers/friends for an annual golf trip we do. Beautiful property, well maintained, and plenty of space for everyone. Will for sure be looking to rent this property again if we have another trip nearby."
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Air Conditioning
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Outside
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (145)
"Cozy little cabin in the woods "
The price is SAR 638
SAR 1,388 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
9.4 out of 10, Exceptional, (18)
"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
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.