Search Chalets in Chester from CA $117

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Browse Select Chester Chalets

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (37)
"Really enjoyed this home. Was a weekend getaway with friends and there was lots of room for us. Especially enjoyed the sauna. Kitchen is well stocked. All was great. "
Beautiful Manchester VT Mountain Retreat w/Hot Tub

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (12)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is CA $277
CA $705 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Creekside Chalet centrally located near 4 ski resorts

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

10.0 out of 10, Exceptional, (4)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Mountain chalet

10.0 out of 10, Exceptional, (41)
"Great, well kept and supplied house. Had a great ski weekend. Great kitchen and family area."
Mountain chalet

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

Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck

8.6 out of 10, Excellent, (11)
"When we first arrived we couldn’t find extra trash bags. We sent a message to the host, Jason, and he replied immediately to assist us. I appreciate the attentiveness and genuine hospitality. This place is cozy and clean. Made for the perfect weekend getaway!"
The price is CA $484
CA $1,133 total
includes taxes & fees
Sep 1 - Sep 2
Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck

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

10.0 out of 10, Exceptional, (52)
"All around great stay. Had some slight heat issues day 1 that were fixed imemdiately!"
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

9.6 out of 10, Exceptional, (19)
"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 CA $117
CA $521 total
includes taxes & fees
Sep 1 - Sep 2
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

10.0 out of 10, Exceptional, (6)
"We had a great time at the Wine Moose! The sauna kept us super warm in the super cold temps. Very very close to Mt. Snow and we also hit up Berkshire East and Magic an hour south and north respectively, easily. I'd recommend staying here!"
Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

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

10.0 out of 10, Exceptional, (13)
"This spot was perfect for a weekend at mount snow! It was so quick to get to the mountain and good area for food and shops. I would definitely stay here again!"
The price is CA $277
CA $825 total
includes taxes & fees
Aug 26 - Aug 27
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

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

9.8 out of 10, Exceptional, (35)
"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

Private Chalet: walk to hiking/biking trails and golf course

2.0 star property
9.6 out of 10, Exceptional, (5)
"We spent the week, excellent location and the home was exactly as described in listing."
The price is CA $243
CA $784 total
includes taxes & fees
Aug 24 - Aug 25
Private Chalet: walk to hiking/biking trails and golf course

COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

9.8 out of 10, Exceptional, (35)
"Clean, spacious and perfect location!!"
COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

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

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

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
Green Mountain Manor - Ski and Summer Chalet

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (23)
"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

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

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

10.0 out of 10, Exceptional, (4)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
The price is CA $199
CA $662 total
includes taxes & fees
Aug 28 - Aug 29
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

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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Top Chester Hotel Reviews