Holiday Homes in Chester

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Featured Holiday Homes in Chester

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

10.0 out of 10, Exceptional, (43)
"Brad was a wonderful host and the home and area had so much for us to do. It was the perfect place to get away and be with friends. "
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.8 out of 10, Exceptional, (17)
"This is a beautiful property with beautiful views, lots of indoor and outdoor space for the little ones to play, and for the adults to chill and socialize. Very clean and well kept. We would love to come back and stay here again in the future!"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (31)
"Clean house and glad we were able to bring our dog. Close to so many great mountains and rivers to explore. Great shower pressure. Wish there were some picnic tables or outdoor eating spaces on the sunny property."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

BruinsDen - Ski On Ski Off (Home Stretch Trail)

9.8 out of 10, Exceptional, (9)
"My family and I stayed for a week at this home. The pictures do not do this home justice! It was very clean, well equipped with everything we needed and very spacious. The beds were really comfortable, showers were really nice and everything was stocked with all the essentials. We cooked breakfast every morning and dinner a few evenings and had everything we needed. Check in process was easy and all the details were clearly defined for checkout (also easy). The property is nice and private with...
The price is AU$1,089
includes taxes & fees
2 Dec - 3 Dec
BruinsDen - Ski On Ski Off (Home Stretch Trail)

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

10.0 out of 10, Exceptional, (32)
"We had the most enjoyable and comfortable stay at this lovely home away from home! Jen was more than welcoming and always very responsive. The house was very clean and located conveniently across the street from the mountains. Looking forward to staying here again next season! :)"
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

10.0 out of 10, Exceptional, (64)
"We had several events during our son's wedding weekend. The house and barn made for a great landing spot between events. We had plenty of room for all of our family. The property was very large and allowed for several sitting areas, both inside and outside. The landscape around the house made a great backdrop for pictures for the groom and groomsmen. The house has everything you need. "
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

S'Mookie the Bear- ski on and off, hot tub, pool

9.0 out of 10, Wonderful, (2)
"Wonderful four bedroom place that fit our family well. Very well stocked for cooking. Easy walk to ski in/ ski out."
S'Mookie the Bear- ski on and off, hot tub, pool

Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

9.0 out of 10, Wonderful, (4)
"Very Clean, roomy, nicely laid out, close to ski areas. Owner was responsive and available. All went very well. I would recommended this without reservation."
Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

10.0 out of 10, Exceptional, (17)
"We had an amazing stay at this spacious townhome, just across from Mount Snow. The location was perfect for hiking, with stunning trails to explore throughout the area. We spent our days hiking and taking in the beautiful mountain views. The townhome is beautifully decorated and very comfortable. The living area with a cozy wood-burning fireplace was perfect for relaxing after a day outdoors. The fully equipped kitchen made it easy to cook and enjoy meals together, and we loved spending time on...
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (21)
"Everything was clean and comfortable and had a great view from the living room/primary bedroom. Because we were there for a wedding we didn't use the kitchen or really get to enjoy all the amenities but the proximity to Woodstock was an added bonus. The shower head in the shared bathroom could use updating but really that's a small complaint. All in all we had a great stay."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

10.0 out of 10, Exceptional, (22)
"GREAT TIME ! GREAT HOUSE"
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Family oriented community in country setting...10 minute walk to town center.

10.0 out of 10, Exceptional, (19)
"The property was really perfect. In perfect condition. Spotlessly clean. Nice views of the mountains. Great location for access to amenities."
Family oriented community in country setting...10 minute walk to town center.

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

10.0 out of 10, Exceptional, (3)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.