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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 114 Chalets in Chester with updated reviews, rates, and availability.

Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Smart TV, DVD player, books

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"The place was nice, the hosts were really excellent and responsive- and the location is very nice. It’s not too far to go hiking, swimming or kayaking!!!"
The price is AED 727
AED 1,744 total
includes taxes & fees
5 Jun - 6 Jun
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (2)
"All the beds were comfortable and plenty of beds. The grounds are great and the deck is very nice. Its a Beautiful area. Very well maintained. We will differently go again. "
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Okemo Mountain Chalet W/ Hot Tub and Game Room
Exterior

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (159)
"Great house, great host"
Okemo Mountain Chalet W/ Hot Tub and Game Room
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Smart TV, fireplace, computer monitors

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

8.8 out of 10, Excellent, (3)
"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Exterior

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (51)
"We enjoyed skylight lodge. We get together with family and friends each year to do an annual fundraising event. The house was perfect for our group. The big fireplace was a great way to relax after a day of skiing or snowshoeing. "
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Cozy Creekside Chalet centrally located near 4 ski resorts
Exterior

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (9)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AED 733
AED 1,866 total
includes taxes & fees
30 Jun - 1 Jul
Cozy Creekside Chalet centrally located near 4 ski resorts
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Outdoor dining

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

10.0 out of 10, Exceptional, (6)
"Helpful, fun and warm. "
The price is AED 584
AED 2,353 total
includes taxes & fees
5 Jun - 6 Jun
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior

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

10.0 out of 10, Exceptional, (39)
"Noreen was very communicative and the house was great. Had everything we needed and more than enough room for 2 five person families. It was in a great location—quick drive to the mountain. "
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Fridge, microwave, oven, stovetop

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"What a great escape. Plenty of space for plenty of folks, beautifully designed. Dining room table is gorgeous. Hosts were quick to respond throughout the process, would come back."
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Outdoor spa tub

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (34)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
The MountainTop
Interior

The MountainTop

10.0 out of 10, Exceptional, (1)
"Nick’s cabin was perfect. Beautifully built and decorated, the cabin was amazing. Nick’s place had everything we needed and more. The location was tucked away with beautiful surroundings and close to Stratton mountain. Nick was always quick to reply with any questions and made sure our stay was perfect. Only regret is we didn’t stay here longer! "
The MountainTop
Summer outdoor getaway near Wilmington and beautiful Mt. Snow.
Dining

Summer outdoor getaway near Wilmington and beautiful Mt. Snow.

10.0 out of 10, Exceptional, (23)
"Great place, close to everything, all amenities and most importantly great hosts!"
Summer outdoor getaway near Wilmington and beautiful Mt. Snow.
Stylish Mountain Getaway close to Stratton w/ Spa
Aerial view

Stylish Mountain Getaway close to Stratton w/ Spa

9.8 out of 10, Exceptional, (7)
"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "
Stylish Mountain Getaway close to Stratton w/ Spa
Modern 4-Bedroom Mountain Retreat Minutes to Lake Rescue & Echo and Hiking
Private kitchen

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
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
Terrace/patio

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

10.0 out of 10, Exceptional, (15)
"We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!"
The price is AED 389
AED 1,494 total
includes taxes & fees
3 Jun - 4 Jun
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Interior

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

10.0 out of 10, Exceptional, (24)
"We had 4 families with a range of kids from 16-5. The house was the perfect space to spread out to give everyone space and things to do! The house was clean and stocked with whatever you needed during the stay. We’ve done a lot of VRBO rentals and this was one of our best experiences! Plus, the trail was amazing to have in the backyard! "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Fridge, microwave, oven, stovetop

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.2 out of 10, Wonderful, (7)
"Nice hill for sledding. Missed having electric mixer for potatoes. Nice community area of kitchen, dining room and living room. Good setup of rooms. "
The price is AED 783
AED 2,371 total
includes taxes & fees
8 Jun - 9 Jun
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Fridge, microwave, oven, stovetop

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (35)
"Stayed 3 nights everything was spotless & so very comfortable. This was our 2nd stay here. The host is always reachable & prompt to respond. Can’t wait to hopefully stay here again. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
New! Mt Snow Chalet w/land, privacy, relaxation
Outdoor dining

New! Mt Snow Chalet w/land, privacy, relaxation

9.2 out of 10, Wonderful, (5)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
New! Mt Snow Chalet w/land, privacy, relaxation
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Property grounds

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!
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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