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Compare 20 Chalets in Charlestown with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (10)
"Super cozy and very clean. As described. Convenient to Magic Mountain- not a walk with ski gear on (at least for us!) but a 3 min drive. Master bed was very comfortable. "
Cozy Chalet on Magic Mountain. Close to Stratton, Bromley and Okemo.

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

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

10.0 out of 10, Exceptional, (21)
"This is a great property, large enough and with bedrooms and living areas so that our group of 20 could be together and also spread out for some relative privacy. The skiing at Okemo in January was some of the best it has been in years. We have stayed at this property in the past, and enjoyed it just as much this time around. We did miss the hot tub though. The place is well appointed and clean. Communication with the owner was excellent, and he was accommodating for our requests. If your...
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

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 2,160 total
includes taxes & fees
23 Feb - 24 Feb
Cozy Creekside Chalet centrally located near 4 ski resorts

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

10.0 out of 10, Exceptional, (7)
"Our group came for ski trip and New years. A well maintened, clean and spacious Chalet. Everything was as advertised. Highly recommend. "
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK

Mountain chalet

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

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

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

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

10.0 out of 10, Exceptional, (34)
"This was the second time we have stayed at this property and it did not disappoint. Plenty of room for everyone. Clean and well furnished. Highly recommend it."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

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.

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

9.6 out of 10, Exceptional, (31)
"We had a fabulous stay here. Owner was v communicative and accommodating."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

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

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

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

Off-grid chalet w fireplace, pet-friendly - Skiing, Snowmobiling, Snowshoeing

2.0 star property
10.0 out of 10, Exceptional, (8)
"The house was exactly as described and shown in the pictures. The location is PERFECT. About 10 minutes from Okemo with the cute downtown area with shops and restaurants. If it was in ski season we would be in heaven! The layout was so good for family/friends with the upstairs and downstairs bedrooms and the hosts had the home immaculate with a great eye for a cozy design and added features. The kitchen was fully stocked with everything a person would need- and a little welcome gift for the...
Off-grid chalet w fireplace, pet-friendly - Skiing, Snowmobiling, Snowshoeing

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

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

10.0 out of 10, Exceptional, (1)
"The house was clean and organized. The host was easy to communicate with. "
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

10.0 out of 10, Exceptional, (10)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Swiss Chalet Family Retreat w/ lake access

Swiss Chalet Family Retreat w/ lake access

Brand new Appliances, Deck & Hot Tub - 1 min from Okemo base & Ludlow Downtown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Well appointed house for one or two families. Kitchen well stocked - both equipment and basics (spices), nice game room, fireplace/lounging area with great view on the valley. Few minutes drive to Okemo or town. Lots of details considered. TVs with Sonos. Toilet paper & bath amenities could use a step up in quality (given price point of house). Given cleaning fee, would be nice to remove the departure requirements. Appreciated the late check-out."
Brand new Appliances, Deck & Hot Tub - 1 min from Okemo base & Ludlow Downtown!

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

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

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"Everything was fantastic! Owner was amazing and so helpful and understanding. We had plenty of room as a family of 5 full over full bunk with full trundle - fireplace was great for ambiance. Ski on ski off so easy access gor a lunch break! Would definitely stay again."
Ski In/Out Studio at Okemo on Sachem Trail

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is AED 551
AED 1,172 total
includes taxes & fees
12 Feb - 13 Feb
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (152)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AED 624
AED 1,341 total
includes taxes & fees
5 Feb - 6 Feb
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.