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

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

9.0 out of 10, Wonderful, (4)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
New! Mt Snow Chalet w/land, privacy, relaxation

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

10.0 out of 10, Exceptional, (4)
"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 SAR 469
SAR 1,361 total
includes taxes & fees
1 Apr - 2 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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

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 SAR 1,313
SAR 3,344 total
includes taxes & fees
1 Apr - 2 Apr
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

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

10.0 out of 10, Exceptional, (106)
"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

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

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

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.

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,

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

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

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

10.0 out of 10, Exceptional, (3)
"We were two families - 4 adults, 5 kids aging from 5 to 13. The house offered everything we would have wanted for a fun vacation. The kids loved the arcade room and the theatre (and the hot tub!). The adults loved the beauty and charm of the cabin, the very well equipped kitchen, and the hot tub too! Its super close to the ski mountain, and a local market. Even our dog wanted to stay when it was time to leave. I might suggest packing extra towels if you use the hot tub often, but otherwise...
The price is SAR 728
SAR 2,620 total
includes taxes & fees
1 Apr - 2 Apr
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

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

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

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

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 SAR 357
SAR 1,289 total
includes taxes & fees
1 Apr - 2 Apr
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

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 859
SAR 2,092 total
includes taxes & fees
1 Apr - 2 Apr
Cozy Creekside Chalet centrally located near 4 ski resorts

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

2.0 star property
10.0 out of 10, Exceptional, (10)
"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 SAR 746
SAR 1,786 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

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.
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Other property types in Chester

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

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

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 SAR 1,268
SAR 1,576 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
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.