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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 101 Chalets in Chester with updated reviews, rates, and availability.

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

9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
The price is AED 1,447
AED 3,515 total
includes taxes & fees
31 Mar - 1 Apr
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, (32)
"We had 9 people in 2 family units staying at house. Then about another 6 that came each night to hang out. Plenty of room. 3 living room areas for everyone to spread out. Best stocked home EVER!!! There was literally everything and anything that we needed…..and then some. Inside sauna so cool. Unfortunately way too cold to go out and enjoy the hot tub. Decorations beyond beautiful. Owner very quick with communication. Highly recommend staying here. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub
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, (124)
"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!
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, (106)
"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
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
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)
"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 chalet near Wilmington and beautiful Mt. Snow.
Dining

Ski chalet 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!"
Ski chalet near Wilmington and beautiful Mt. Snow.
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 spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is AED 841
AED 2,053 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (33)
"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,
1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop
Outdoor dining

1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop

10.0 out of 10, Exceptional, (3)
"The house was great for our family of 5 and our dog. Located so close to Mt. Snow, it was an easy drive, clean and had anything we needed to cook and relax. The hosts are very communicative!"
The price is AED 907
AED 2,826 total
includes taxes & fees
31 Mar - 1 Apr
1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop
The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!
Fridge, microwave, oven, stovetop

The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!

10.0 out of 10, Exceptional, (3)
"Excellent. No complaints "
The price is AED 1,010
AED 2,017 total
includes taxes & fees
24 Mar - 25 Mar
The Snow Owl Chalet in Dover, Gorgeous 4-Bd 3-Bath - 10 Min. to Mount Snow!
"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, (33)
"Fun place. Great light with the large window and fun to have the hot tub. Well equipped for cooking and eating for a family of 6. "
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Charming 5BR Chalet@Base of Stratton Mt Has It All
Exterior

Charming 5BR Chalet@Base of Stratton Mt Has It All

9.6 out of 10, Exceptional, (11)
"Our trip this past weekend to Chalet O'Bear was just what we wanted! Booking and communication with the property manager was seamless. Any issues we had were addressed immediately and taken care of. We loved the location of the property and made our stay at Stratton perfect! We will be looking to book again! "
Charming 5BR Chalet@Base of Stratton Mt Has It All
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village

10.0 out of 10, Exceptional, (67)
"House is beautiful, well stocked. Kat was exceptional as host; all my questions were promptly answered. Location is ideal"
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

10.0 out of 10, Exceptional, (4)
"Clean, great location. Pet friendly and well thought out. "
The price is AED 514
AED 1,407 total
includes taxes & fees
8 Apr - 9 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Aerial view

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
Classic Alpine Vermont Chalet
Fridge, microwave, oven, stovetop

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (10)
"The house was just what we needed for a family wedding in Manchester. Quite literally right off the highway but the house itself is nestled back and quiet so you don’t even hear the road. "
Classic Alpine Vermont Chalet
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Outdoor spa tub

8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

10.0 out of 10, Exceptional, (17)
"great space for adults and teenagers. loved the hot tub! "
The price is AED 713
AED 2,308 total
includes taxes & fees
21 Apr - 22 Apr
8 minutes to ski Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Expansive 7-BR Chalet 5-min from Mt. Snow
TV, fireplace, offices

Expansive 7-BR Chalet 5-min from Mt. Snow

10.0 out of 10, Exceptional, (3)
"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...
Expansive 7-BR Chalet 5-min from 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)
"Overall, a very good stay. The house is a bit smaller than we thought, but it was very clean and well stocked. The indoor fireplace and provided wood was a nice perk. The hot tub was not clean or well kept, so beware of that. There were body hairs and a brown scum ring around the edge."
Stylish Mountain Getaway close to Stratton w/ Spa
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 Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Miscellaneous

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.