Search Chalets in Chester

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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

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)
"Fun place"
New! Mt Snow Chalet w/land, privacy, relaxation
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, (6)
"Anthony and Haleigh are incredibly easy to work with and very fast communicators. The cabin was very clean, and exactly as advertised. We stayed here to ski at Mt. Snow. A short, picturesque ride through the mountains to Mt. Snow, and at the end of the day, you don't have to go through traffic heading towards Mt. Snow businesses to get home. My 10 year old son and his friend loved the loft, with views of the river, and my 13 year old daughter loved having her own room. We cooked breakfast...
The price is AED 496
AED 1,370 total
includes taxes & fees
29 Apr - 30 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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
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 1,286
AED 3,275 total
includes taxes & fees
21 Apr - 22 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
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)
"The house was equipped with everything we needed! Cant wait to 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
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, (50)
"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
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.
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)
"Great stay"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
"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)
"Had a lovely weekend with "
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
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, (5)
"Doug and Rose are incredible hosts! The property was immaculate and had one of the best finished basements we've ever stayed at. Our group of friends do an annual snowboard trip on the east coast and this house will definitely be in the rotation. Would highly recommend!"
The price is AED 635
AED 2,449 total
includes taxes & fees
16 Apr - 17 Apr
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Spacious Vermont Chalet for Group Getaways
TV, fireplace, offices

Spacious Vermont Chalet for Group Getaways

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...
Spacious Vermont Chalet for Group Getaways
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
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)
"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
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 349
AED 1,274 total
includes taxes & fees
20 Apr - 21 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
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 915
AED 2,147 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts
Calling all hikers, bikers, golfers, kayakers, swimmers for summer fun
Property grounds

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
Green Mountain Manor - Ski and Summer Chalet
Property grounds

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Relaxing VT stay . You are in a rural setting but places to stock up on supplies was less then 10 miniutes away . We watched the fireworks that stratton displayed pretty much from the comfort of the property .Our children are young adults and they had a blast finding local swimholes . As well as spending a day at Bromley Mountain ( 20 mins away ) where they did water slides , alpine slides , the giant swing to name a few . House is large and the ability to accomodate large families or groups ....
Green Mountain Manor - Ski and Summer Chalet
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 Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

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, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (16)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,332 total
includes taxes & fees
21 Apr - 22 Apr
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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.