Photo by The Curious Zephyr

Search Chalets in Charlestown

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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

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

9.8 out of 10, Exceptional, (123)
"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!

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

10.0 out of 10, Exceptional, (23)
"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

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

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 SAR 896
SAR 2,147 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Creekside Chalet centrally located near 4 ski resorts

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

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 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

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

9.6 out of 10, Exceptional, (32)
"Property was great, as described in listing! Rooms were clean and overall tidy. John was easy to communicate with and ensured we had everything before arriving. Would stay again if available."
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"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 SAR 746
SAR 1,768 total
includes taxes & fees
16 Mar - 17 Mar
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun

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.

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

10.0 out of 10, Exceptional, (3)
"Our ski weekend at this 3-bedroom chalet in Bradford, NH, was absolutely perfect. The location was ideal for our trip, with Pats Peak just a 15 minute drive away. It made hitting the slopes quick and easy, allowing us to maximize our time skiing.The chalet itself was spacious and well-equipped for our family. With three cozy bedrooms and two living rooms, there was plenty of space for everyone to relax after a full day on the mountain. The kitchen had everything we needed to cook meals, and we...
3-bedroom chalet next to skiing, hiking, boating and breweries

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

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

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

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

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

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

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

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

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
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.
Don't see what you're looking for?
See all available properties in Charlestown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Charlestown

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (68)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 409
SAR 1,185 total
includes taxes & fees
25 Mar - 26 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is SAR 825
SAR 1,548 total
includes taxes & fees
16 Mar - 17 Mar
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (155)
"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 SAR 638
SAR 1,365 total
includes taxes & fees
17 Mar - 18 Mar
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.