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Chalets in Charlestown

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."
The price is AED 3,669
AED 7,338 total
includes taxes & fees
Aug 10 - Aug 11
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

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

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (11)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is AED 733
AED 1,878 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Creekside Chalet centrally located near 4 ski resorts

Off-grid, pet-friendly home base with fire pit for fall foliage adventure

2.0 star property
10.0 out of 10, Exceptional, (12)
"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 AED 1,131
AED 2,254 total
includes taxes & fees
Jul 30 - Jul 31
Off-grid, pet-friendly home base with fire pit for fall foliage adventure

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

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!

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

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.

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

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,

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

10.0 out of 10, Exceptional, (39)
"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

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 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

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

Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

10.0 out of 10, Exceptional, (14)
"The house was wonderful. House was clean. Our family had a wonderful time playing in the backyard. Close to numerous ski towns. The bunkbed downstairs was a nice surprise."
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Stratton Mountain Escape w Hot Tub|Deck|Projector

10.0 out of 10, Exceptional, (1)
"My family loved our stay. Would strongly recommend!"
Stratton Mountain Escape w Hot Tub|Deck|Projector

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 AED 804
AED 2,358 total
includes taxes & fees
Aug 11 - Aug 12
Stylish Farmhouse - Close to Ski, Golf + Hot Tub

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

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access

Cozy Chalet in Vermont's Golden Triangle

9.2 out of 10, Wonderful, (7)
"Great proximity to magic! Well equipped kitchen. Comfortable beds."
Cozy Chalet in Vermont's Golden Triangle
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