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

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Stratton Loft with Pool
8.0 out of 10, Very Good, (4)
"We arrived at 7pm left at 8am . Hence short stay What a great place. Perfect for 2 families loved the living room and kitchen . We be back for longer :-)"
The price is AED 624
AED 1,565 total
includes taxes & fees
20 Jun - 21 Jun
Stratton Loft with Pool
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (29)
"We had a great stay here! Looked just like the pictures. We especially loved the hot tub. Would love to come back."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
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Okemo Mountain Chalet W/ Hot Tub and Game Room
9.8 out of 10, Exceptional, (151)
"Great property for large groups with plenty of space and amenities for everyone. Excellent communication from owner to ensure a perfect stay before, during and after."
Okemo Mountain Chalet W/ Hot Tub and Game Room
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 1,462
AED 3,454 total
includes taxes & fees
23 Jun - 24 Jun
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.
10.0 out of 10, Exceptional, (4)
"Excellent home to reconnect with family when not on the slopes!! Hosts were the best!! Thank you!!!"
BOGO Sale, Golf, Hiking, pool table, pac man, 4bedrooms with private baths.
Hot Tub and Enough Space for 14!
The price is AED 786
AED 1,980 total
includes taxes & fees
20 Jun - 21 Jun
Hot Tub and Enough Space for 14!
WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.
9.8 out of 10, Exceptional, (31)
"Close to EVERYTHNIG!"
WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.
Ski Chalet
10.0 out of 10, Exceptional, (1)
"Even before we left for our vacation, our Host Heather was amazing. She would contact me to make sure we had everything we needed beforehand to make sure our week went flawless. She was so quick to respond to any questions I had. When we pulled into the private driveway, we were greeted with a forest of beautiful evergreen trees that surrounded the property. Then, we opened the door and found this amazing beautiful pristine house. This is one of the cleanest homes I have ever stayed at. Heather...
Ski Chalet
LUXE Forest Retreat
The price is AED 1,113
AED 1,722 total
includes taxes & fees
20 Jun - 21 Jun
LUXE Forest Retreat
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
10.0 out of 10, Exceptional, (5)
"We had a lovely weekend ski trip with friends here and everything was excellent. The house was even more beautiful in person than in the photos. Plenty of room in the driveway for lots of cars, had a tricky time connecting the Bluetooth speaker to the projector but our host Eric was very helpful in talking us through how to connect it. Hot tub was hot and worked great all weekend, I was honestly very impressed with how well it was able to maintain its heat in single digit temperatures outside....
The price is AED 1,763
AED 4,687 total
includes taxes & fees
1 Jul - 2 Jul
Amazing 3-Level Chalet; 2 Kitchens, 2 Decks, HOT TUB, 5 Ski Mountains, Pets OK
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
10.0 out of 10, Exceptional, (16)
"From my first inquiry Dave had been responsive snd helpful. Beautiful house and we couldn’t ask for closer to Okemo trails. So much room in the home for all 17 of us. A fall trip back might be in our future for leave changing views."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Cozy Creekside Chalet centrally located near 4 ski resorts
10.0 out of 10, Exceptional, (6)
"The location was great for skiing at Okemo, and the house was cozy and just the right size for two sets of parents and two tween girls. The kitchen was surprisingly well provisioned for a VRBO."
The price is AED 1,003
AED 2,154 total
includes taxes & fees
20 Jun - 21 Jun
Cozy Creekside Chalet centrally located near 4 ski resorts
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester
Beautiful Manchester VT Mountain Retreat w/Hot Tub
10.0 out of 10, Exceptional, (24)
"All was as advertised and clean and great communication with host Hot tub under the deck so we didn’t use it pool table great but in a tight space so hard to get all the needed shots but no big deal for fun games of pool Overall a great stay and a great place!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Green Mountain Manor - Ski and Summer Chalet
10.0 out of 10, Exceptional, (6)
"The house is huge and has a giant finished basement perfect for the kids to retreat to. The kitchen had every appliance you can think of and the pizza oven worked perfectly. Hot tub outside was the icing on the cake after a day of skiing. The kids were also sledding on the golf course. The shuttle that comes right to the house made this super easy to get everyone to the mountain together. Will definitely stay again! Maybe for a golf retreat next time."
Green Mountain Manor - Ski and Summer Chalet
Bear Paw Cabin - Game Room•Fire Pit•Golf•Hike
10.0 out of 10, Exceptional, (12)
"We had a great stay at the Bear Paw Cabin for our annual VT trip! The house is well appointed and had everything we needed for our stay! Close to Stratton and even closer to Mount Snow, we spent two days at the mountain skiing and snowboarding before hitting the brewery and a local restaurant. The game room is fun, though you will need to bring/buy wood and give the woodstove plenty of time to warm up in the Winter. Our only "con" was that sound traveled easily (one of the bedrooms was open-air...
Bear Paw Cabin - Game Room•Fire Pit•Golf•Hike
8min to Mt. Snow, Hot Tub, Fire Pit, Game Room, Hike, Bike, Explore, Petfriendly
10.0 out of 10, Exceptional, (14)
"Great place to stay! Very roomy, everything was nice and clean! We had an amazing weekend!"
The price is AED 812
AED 2,384 total
includes taxes & fees
20 Jun - 21 Jun
8min to Mt. Snow, Hot Tub, Fire Pit, Game Room, Hike, Bike, Explore, Petfriendly
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
10.0 out of 10, Exceptional, (32)
"We enjoyed our stay. Noreen was very responsive when we had questions. Great location to Okemo."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
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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.

Other property types in Chester

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (179)
"My husband and I loved this little cottage , we will definitely be back."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (70)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is AED 1,178
AED 1,408 total
includes taxes & fees
23 Jun - 24 Jun
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.

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