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Compare 83 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

Mid-Century Arty Chalet - 2 Min to Stratton Slopes

10.0 out of 10, Exceptional, (2)
"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

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

10.0 out of 10, Exceptional, (13)
"Six of us women from Vermont golf courses stayed while playing a tournament at Haystack Country Club. The house suited us perfectly. We had some issues with the bathtub plumbing not turning off but we had prompt attention from a service person. The house had a great kitchen and tv to accommodate us."
The price is AED 655
AED 1,669 total
includes taxes & fees
27 Feb - 28 Feb
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (31)
"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

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

9.6 out of 10, Exceptional, (10)
"Our multi-generational group had a wonderful stay at this perfect ski house! The house is well represented by the listing photos. It’s clean, spacious, and had everything we needed. I had several questions for the owner before and during our stay. His responses were timely and helpful. We would love to stay here again! "
Charming 5BR Chalet@Base of Stratton Mt Has It All

Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

10.0 out of 10, Exceptional, (8)
"Great hosts who communicated clearly. Everything was as listed/pictured. Location is super close to Mount Snow. Snow was plowed in a very timely manner on both the driveway and the street. Plenty of space for the family to spread out, lots of fun with the games & pebble stoves heated the place up so nicely. "
The price is AED 1,286
AED 2,893 total
includes taxes & fees
26 Feb - 27 Feb
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

Modern Lux Cabin w/ Mtn Views | Fire Pit

Modern Lux Cabin w/ Mtn Views | Fire Pit

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

10.0 out of 10, Exceptional, (2)
"We had a fun long weekend close to mount snow. The house was clean, spacious and had fun amenities for the kids after skiing. The greatest entry room for all the ski stuff and plenty of hooks to hang everything else. "
1 Mile To Ski at Mt Snow, FirePit, Hot Tub, Theater & Game Rooms, Moover stop

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

10.0 out of 10, Exceptional, (9)
"Just got back from three nights at this wonderful property with a group of 50-somethings to compete in a gravel bike race. This property was ideally located near our start line, very very clean, plenty of room for us, basically as advertised. Would definitely rent here again in the future given all of the above.."
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Ski chalet near Wilmington and beautiful Mt. Snow.

10.0 out of 10, Exceptional, (22)
"This was our second time staying at the ski chalet. Great location to Mount Snow and local restaurants. House was the perfect size for us. The wood stove and glove rack/cloth hooks was a nice way to dry our ski gear. Check in and check out was super easy. "
Ski chalet near Wilmington and beautiful Mt. Snow.

Cozy Chalet on Magic Mountain. Close to Stratton, Bromley and Okemo.

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 Chalet on Magic Mountain. Close to Stratton, Bromley and Okemo.

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

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

10.0 out of 10, Exceptional, (22)
"This is a great property, large enough and with bedrooms and living areas so that our group of 20 could be together and also spread out for some relative privacy. The skiing at Okemo in January was some of the best it has been in years. We have stayed at this property in the past, and enjoyed it just as much this time around. We did miss the hot tub though. The place is well appointed and clean. Communication with the owner was excellent, and he was accommodating for our requests. If your...
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

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 2,139 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Creekside Chalet centrally located near 4 ski resorts

WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

9.8 out of 10, Exceptional, (34)
"Clean, spacious and perfect location!!"
WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

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

9.8 out of 10, Exceptional, (32)
"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

Mandy's Mountain Chalet minutes from Mount Snow,

10.0 out of 10, Exceptional, (7)
"We had a very nice stay at Mandy’s Mountain Chalet. We had a nice lazy Christmas with TV and a lot of nice food :) maybe the pellet fireplace is not the coziest option, but it was definitely practical. "
The price is AED 551
AED 1,602 total
includes taxes & fees
4 Mar - 5 Mar
Mandy's Mountain Chalet minutes from Mount Snow,
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, (22)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,514
AED 1,882 total
includes taxes & fees
2 Mar - 3 Mar
Long Trail House at Stratton Mountain Resort

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.