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Search Chalets in Charlestown from CA $277

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Browse Select Charlestown Chalets

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (12)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is CA $277
CA $705 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Creekside Chalet centrally located near 4 ski resorts

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

10.0 out of 10, Exceptional, (4)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Mountain chalet

10.0 out of 10, Exceptional, (41)
"Great, well kept and supplied house. Had a great ski weekend. Great kitchen and family area."
Mountain chalet

3-bedroom chalet next to skiing, hiking, boating and breweries

10.0 out of 10, Exceptional, (6)
"We had a great time staying here and skiing at Mt. Sunapee. Highly recommend."
3-bedroom chalet next to skiing, hiking, boating and breweries

Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

9.6 out of 10, Exceptional, (5)
"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

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

9.8 out of 10, Exceptional, (125)
"We found the hosts to be super helpful and friendly. Location was fantastic. We loved the hot tub and wood burning stove. It was a perfect stay for my extended family and I. The beds were also super comfortable-we slept great! We would definitely recommend this spot!"
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

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

Stylish Farmhouse - Close to Ski, Golf + Hot Tub

10.0 out of 10, Exceptional, (6)
"Very large, bright and completely remodeled. Plenty of space for a large family to hang out in the kitchen area and living room."
The price is CA $314
CA $899 total
includes taxes & fees
Sep 2 - Sep 3
Stylish Farmhouse - Close to Ski, Golf + Hot Tub

Stratton Mountain Escape w Hot Tub|Deck|Projector

10.0 out of 10, Exceptional, (2)
"My family loved our stay. Would strongly recommend!"
Stratton Mountain Escape w Hot Tub|Deck|Projector

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (160)
"This was our second time staying at the Bear Chalet and we absolutely loved it. So much space for multiple families and very kid friendly!"
Okemo Mountain Chalet W/ Hot Tub and Game Room

Modern Chalet by Mt. Sunapee

Modern Chalet by Mt. Sunapee

Okemo 6 Bedroom Chalet.

9.4 out of 10, Exceptional, (23)
"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "
Okemo 6 Bedroom Chalet.

Fall into Cozy at Bigfoot Chalet

2.0 star property
10.0 out of 10, Exceptional, (13)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
The price is CA $279
CA $663 total
includes taxes & fees
Sep 1 - Sep 2
Fall into Cozy at Bigfoot 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 On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

9.6 out of 10, Exceptional, (33)
"We had a fabulous stay here. Owner was v communicative and accommodating."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Cozy Chalet 2 min drive to Okemo Base and Downtown, and 5 min to Jackson Gore.

Cozy Chalet 2 min drive to Okemo Base and Downtown, and 5 min to Jackson Gore.

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

10.0 out of 10, Exceptional, (40)
"This is our second year staying at this beautiful home. We love the space and amenities, not to mention the location to the mountain. The owners have been very accommodating and communicative. Overall, a wonderful stay for our group of families and hope to return again when we come back to Ludlow."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

10.0 out of 10, Exceptional, (10)
"Great house, made our ski weekend easy and fun. House is better than the pictures."
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks

9.6 out of 10, Exceptional, (5)
"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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Top Charlestown Hotel Reviews