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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

Chalets in Chester

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

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."
The price is SAR 3,748
SAR 7,495 total
includes taxes & fees
10 Aug - 11 Aug
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Outdoor spa tub

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
Mid-Century Arty Chalet - 2 Min to Stratton Slopes
Terrace/patio

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
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, (10)
"We spent a great week in Weston. Great location to ski Stratton. Hosts were very responsive. Would def go back."
The price is SAR 579
SAR 1,699 total
includes taxes & fees
28 Jul - 29 Jul
Cozy Creekside Chalet centrally located near 4 ski resorts
New! Mt Snow Chalet w/land, privacy, relaxation
Property grounds

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

9.2 out of 10, Wonderful, (5)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
New! Mt Snow Chalet w/land, privacy, relaxation
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, (51)
"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
Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Outdoor spa tub

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
Pet-friendly escape to Vermont for fall foliage and fun
Exterior

Pet-friendly escape to Vermont for fall foliage and fun

2.0 star property
10.0 out of 10, Exceptional, (12)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
The price is SAR 807
SAR 1,871 total
includes taxes & fees
30 Jul - 31 Jul
Pet-friendly escape to Vermont for fall foliage and fun
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities
Exterior

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

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

10.0 out of 10, Exceptional, (12)
"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 SAR 735
SAR 2,196 total
includes taxes & fees
4 Aug - 5 Aug
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
The MountainTop
Exterior

The MountainTop

10.0 out of 10, Exceptional, (1)
"Nick’s cabin was perfect. Beautifully built and decorated, the cabin was amazing. Nick’s place had everything we needed and more. The location was tucked away with beautiful surroundings and close to Stratton mountain. Nick was always quick to reply with any questions and made sure our stay was perfect. Only regret is we didn’t stay here longer! "
The MountainTop
Stylish Mountain Getaway close to Stratton w/ Spa
Outdoor dining

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
Exterior

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

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!"
Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Outdoor spa tub

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

10.0 out of 10, Exceptional, (7)
"The house was great for our family of 5 and our dog. Located so close to Mt. Snow, it was an easy drive, clean and had anything we needed to cook and relax. The hosts are very communicative!"
The price is SAR 739
SAR 2,633 total
includes taxes & fees
27 Jul - 28 Jul
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Green Mountain Manor - Ski and Summer Chalet
Property grounds

Green Mountain Manor - Ski and Summer Chalet

9.0 out of 10, Wonderful, (8)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
Green Mountain Manor - Ski and Summer Chalet
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Exterior detail

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (35)
"Brought friends from overseas to show them the Northeast, this remote house in the mountains was the perfect spot. It was not to far from the small cute town but far enough that it was extremely relaxing. The hot tub and fire was perfect, and the kitchen was wonderful to cook in 10/10 Excellent Stay!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub
Classic Stratton Ski Chalet: Perfect for Families
Exterior detail

Classic Stratton Ski Chalet: Perfect for Families

10.0 out of 10, Exceptional, (1)
"Enjoyed our three night stay here. The kitchen is well stocked with pots and pans, dinnerware, silverware, utensils, etc. Beds were very comfortable. Our only disappointment was that we couldn't have a fire in the fireplace as the chimney was in need of repairs. Hope to be back next year."
Classic Stratton Ski Chalet: Perfect for Families
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Outdoor spa tub

8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

10.0 out of 10, Exceptional, (19)
"great space for adults and teenagers. loved the hot tub! "
The price is SAR 1,013
SAR 2,692 total
includes taxes & fees
1 Aug - 2 Aug
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
"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, (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
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

On The River Inn

On The River Inn

10/10 Excellent
"We really enjoyed our stay. Beautiful place, very clean."
Andrew 2-night trip
Posted 2 days ago
On The River Inn