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Compare 27 Chalets in Charlestown with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (24)
"Overall great stay for the family and friends. Communication was easy and available as needed. One issue that arose with people in the studio was handled expeditiously by Dave. Great location and layout for kids and adults to have separate areas. Would highly recommend "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

9.6 out of 10, Exceptional, (33)
"Great stay"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

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

9.6 out of 10, Exceptional, (5)
"Our family of grandparents, parents and young adults enjoyed the house for 3 nights. We skied at the golf course, had a long walk up the road and put together a difficult puzzle (took 3 days). We would have loved a larger table for the puzzle - we brought in one of our car's rear folding covers.The only complaint was the beds - they all have VERY firm mattresses.I told the owner that the toilet paper holder was not secured to the wall in the upstairs bathroom. "
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking

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 AED 915
AED 2,147 total
includes taxes & fees
14 Apr - 15 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts

Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun

2.0 star property
10.0 out of 10, Exceptional, (11)
"We stayed at the Bigfoot Chalet for a last-minute ski trip, and we had a wonderful stay. Home was clean, comfortable, and well-appointed. Convenient to Killington - about a 25-30 min - and a lovely place to unwind at the end of a long day of skiing. We would love to return! "
The price is AED 731
AED 1,748 total
includes taxes & fees
30 Apr - 1 May
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun

Cozy Springtime Retreat on Magic Mountain

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 Springtime Retreat on Magic Mountain

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

9.8 out of 10, Exceptional, (125)
"This house was perfect for two families with teens spending a weekend at Okemo. The mountain was a short drive away. The beds were comfortable and everything was clean. It was nice to have a big table that fit everyone for meals. The hot tub was a nice treat after skiing. It was so convenient that we could bring our dog too. The owner was very responsive to questions. We had a great weekend!"
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)
"Cindy was a pleasure to work with! Her home was exactly as described. We felt very comfortable in her home and the town of Jamaica is so cute! We went to the cutest little general store every morning to get breakfast and lunch. There are plenty of board games to enjoy waiting for you as you arrive… it is 15 minutes from Stratton Mountain. There is a foyer to leave your boots and jackets to hang. "
Two Bedroom Chalet, Charming, Quiet, River Front

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

Mountain chalet

10.0 out of 10, Exceptional, (40)
"Owner is very nice, easy communications. "
Mountain chalet

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.

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, (159)
"Absolutely perfect! Clean, beautiful house with well stocked kitchen, cozy wood stove, comfortable beds, plenty of blankets and pillows, and amazing hot tub. Bob was readily available and helpful. Driveway was even plowed after snow! Can’t wait to stay again!!!"
Okemo Mountain Chalet W/ Hot Tub and Game Room

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

10.0 out of 10, Exceptional, (4)
"We had a lovely time staying in this cozy home with amazing views of the surrounding forest and glimpses of the frozen lake! The main living space and bedrooms have been nicely renovated and furnished and there were ample supplies in the kitchen. It would have been nice to have bathroom toiletries and hairdryers in every bathroom, however we were able to make do. The location was very convenient to Mount Sunapee, where my daughter was participating in an alpine ski race. "
3-bedroom chalet next to skiing, hiking, boating and breweries

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

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

Cozy Chalet in Vermont's Golden Triangle

9.2 out of 10, Wonderful, (7)
"Family of five (kids 4, 8, 11) pup here for skiing at Magic Mountain. Great location, 5 min to mountain and less to a grocery store in the other direction. House was well-quipped but also not overflowing with leftover food or items from previous guests. The basement was a perfect place to put the kids and they loved the foosball table. The fenced in yard was a plus though the snow was high enough that it didn’t actually contain our dog, something other dog owners might want to keep in mind for...
Cozy Chalet in Vermont's Golden Triangle

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

9.6 out of 10, Exceptional, (5)
"Great stay at a very fun ski chalet. Perfect location for skiing at Magic Mountain. The owner really thought of everything. From wireless phone chargers in every bedroom, to labeling all of the kitchen cabinet to Alexa in every room to help out with music and smart lights. Will be planning another stay at this house and there is so much room we will be inviting more family to join us!"
Green Mt Getaway: Close to Magic, Stratton, Bromley, Okemo Parks

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

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

9.0 out of 10, Wonderful, (4)
"The house was just perfect for our family of six. It was cozy and welcoming; with all the essentials we needed. Everything worked perfectly and the house was warm when we arrived. The gas fireplace was a nice welcome after a day of skiing and the highlight was the hot tub! Unfortunately, the fire-pit was under a ton of snow so we could not use. Jake was very communicative and answered all our questions quickly. Note that a 4WD or AWD car is needed to get up the steep road up to the house. Would...
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Cozy Mountain View Chalet Near Okemo

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 Mountain View Chalet Near Okemo
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

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
Cozy Crescent Cottage

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (156)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is AED 624
AED 1,337 total
includes taxes & fees
14 Apr - 15 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (206)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
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.