Holiday Homes in Chester

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Featured Holiday Homes in Chester

Okemo Mountain Lodging
3.5 star property
7.6 out of 10, Good, (26)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
10.0 out of 10, Exceptional, (8)
"The photos are accurate, but the place seemed even better than I anticipated. It was perfect for our family of 4 (two teen boys) and dog. The weather was rainy and cold for a couple of days, but the house was cozy. The hot tub was great. And also the access the Manchester was a complete surprise to us. We didn't really know where we were going and we were pleasantly surprised to find a quaint town with shops and restaurants. The book store in town was amazing. We did lots of hiking and...
The price is NZ$1,010
includes taxes & fees
1 Oct - 2 Oct
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
4 Season Secluded Lakefront Home near Ski Mountains
9.4 out of 10, Exceptional, (61)
"This is now on our top 10 vacation lists. It is an outstanding location. The water quality is great, and there's a perfect little beach for the very little people. The house is rustic but has everything one might need. The variety of boats allowed us to see around the lake. We hated to leave."
4 Season Secluded Lakefront Home near Ski Mountains
Idyllic Wallingford Retreat - Near Skiing & Hiking
9.8 out of 10, Exceptional, (14)
"Nice loft. Had everything we needed. It had lots of little extras. Everything was very clean with only an exception of a pan that the previous guest had not washed completely. Overall it was very nice."
Idyllic Wallingford Retreat - Near Skiing & Hiking
Peaceful 3-BR Cabin 40-Min to Stratton
2.0 star property
10.0 out of 10, Exceptional, (2)
"To say that this cabin had everything that you could want or need is an understatement! My family and I stayed for a week and during checkout my daughter choked up talking about the great time our family had. We left so rested. "
Peaceful 3-BR Cabin 40-Min to Stratton
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (150)
"Beautiful lake, kayaking, backyard firepit, hiking , such a fun area with a lot to explore.nearby, "
Idyllic Lakefront House Suited Two Families
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, (15)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (36)
"Recently held a staff retreat here, and it was amazing. The space is clean, and has everything you need for a great stay. Host was super responsive. Thank you!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (43)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Elegant Mtn Chalet w/ Deck: 1 Mi to Mt Snow!
10.0 out of 10, Exceptional, (14)
"Wonderful and unique home with plenty of space for family and friends. Well appointed and great communication from owners. Would absolutely stay here again."
Elegant Mtn Chalet w/ Deck: 1 Mi to Mt Snow!
Blueberry Hill Escape Pet Friendly HotTub Fire pit
9.8 out of 10, Exceptional, (12)
"On arrival I loved the breathtaking views of the mountains ! The house was so spacious. Each kid had their own room and my husband and I loved having a master suite ! Our dog was so comfortable there as well ! I am really big on cleanliness and this house was immaculate !! We loved the hot tub! So relaxing ! I walked the dog around the house every morning and had noticed fruit trees ! The peaches were delicious ! Got Home from dinner one night amd we were getting of the car and a black bear...
The price is NZ$905
includes taxes & fees
30 Sept - 1 Oct
Blueberry Hill Escape Pet Friendly HotTub Fire pit
Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.
9.6 out of 10, Exceptional, (43)
"Every year we meet our friends from New York at a new destination. This home was beautiful. Great location. Todd, the owner was wonderful, very quick to respond to my questions. We will definitely be back. Thank you, Todd, for a great stay. Looking forward to next year! "
Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.
Family-Friendly Stratton Gem Close to Slopes!
10.0 out of 10, Exceptional, (7)
"Super comfortable, clean, and close to the slopes. Second time here and will definitely stay again"
Family-Friendly Stratton Gem Close to Slopes!
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
Modern Gnarvana Townhome Quick Walk to Mount Snow: Balcony-Fireplace-Loft-Pets
10.0 out of 10, Exceptional, (10)
"This property was a great find and we would certainly recommend it to anyone. It was very well appointed, super clean, and the open lines of communication with the hosts was perfect. "
The price is NZ$746
includes taxes & fees
24 Sept - 25 Sept
Modern Gnarvana Townhome Quick Walk to Mount Snow: Balcony-Fireplace-Loft-Pets
Log manor on 65 private acres of land with entertaining amenities & hot tub
9.8 out of 10, Exceptional, (6)
"Great property and beautiful views. Not too far from Killington. A wonderful trip to remember. Would definitely stay here again."
Log manor on 65 private acres of land with entertaining amenities & hot tub
Ski on, ski off trailside condo at Okemo
10.0 out of 10, Exceptional, (54)
"Being a ski in/out condo has it's perks. We had a great day skiing and skied back to the condo content for the day. A couple of younger guys decided at 3:30 to go for a few more runs. They were up and boarding in about 2 minutes and got in a great run on Nor'easter and one other. Couldn't do that without a ski in/out unit. Cleaning was a little suspect and the dishwasher was still full of dirty dishes upon arrival, but made do. Thanks."
Ski on, ski off trailside condo at Okemo
Mountainside 5-BR Ski-In/Out Okemo Villa
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a family holiday here, and loved the region, the house location and the house's structure for a large group. The game room was a true hit in the evenings, and the kitchen, living and dining room were so well structured for our group. All appliances worked well, all aspects of the home were clean and well cared for. "
Mountainside 5-BR Ski-In/Out Okemo Villa
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (110)
"A private mountain getaway. Very clean home with all the supplies you need for cooking. We enjoyed our stay in the summer with the areas beautiful views and look forward to seeing it in the winter time!!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
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See all available properties in Chester
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

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (71)
"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!"
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (38)
"Absolutely perfect! Very nice location. Quiet and cozy little townhome. Short drive to Bear Mountain and Killington Ski Resort. Amazing area with plenty of awesome views."
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (13)
"We liked the cottage and the tasteful renovations which preserved its historic nature. Loved the location's privacy and nature surrounding us. It was very warm over our stay and the AC units upstairs and down gave us more comfort. The linens were lovely, even if the mattress was a bit uncomfortable. There were no chairs on the deck and we wanted to sit outside often, so we bought inexpensive chairs and left them there. Our biggest complaint was with Vacasa's oversight. The cleaning crew did not...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
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.