Chester Vacation Rentals

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Browse Select Chester Vacation Homes

Cozy cabin retreat with a high ceiling, central fireplace, and comfortable seating area.

"Beautiful location and so many cozy touches throughout home!"

Enjoy breathtaking views of the snowy landscape from this deck overlooking the serene surroundings.

"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."

Enjoy cooking in this well-equipped kitchen with a wooden dining table and chairs.

"This place was great for my family and I. It is very close to Okemo and town "

Stroll through a vibrant garden featuring a diverse selection of flowering plants and lush greenery.

"I like the location close to mountain walking trails and fine dining options. "

Relax on the deck with a hammock, chairs, and lush green surroundings.

"Only will stay here! "

Enjoy a home away from home with a spacious deck and large windows offering a view of the surrounding trees.

"Nice and roomy. Plenty of room throughout the entire house. Kitchen area LARGE. back deck was nice with the hot tub. Ski run steps from the house. Really nice place."

Stunning two-story house with a steeply pitched roof and inviting front porch, set amidst a beautifully manicured lawn and lush garden.

"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"

Relax in this open-plan room with a sofa, dining table, and chairs, offering a view of the surrounding landscape.

"In town for funeral, the place was great. Very roomy and comfy."

"We had a wonderful stay. The house was very clean and well maintained and very well stocked. The pool and surrounding area were beautiful. We enjoyed day hikes at buttermilk falls and echo lake, which are so close by. We highly recommend this place to anyone looking to spend a few relaxing days in Vermont."

Enjoy cooking in this kitchen with a brick fireplace, large island, and modern appliances.

"Beautiful property "

Situated in a secluded wooded area, this cabin offers a traditional two-story retreat with a balcony and multiple windows.

"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"

Relax in a serene hot tub surrounded by a wooded area and a wooden deck.

"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."

CA $888 total

includes taxes & fees

Aug 11 - Aug 12

Relax in a hot tub on a snow-covered deck.

"Easy booking, clean home, great location and the owner very easy to get in touch with."

CA $944 total

includes taxes & fees

Sep 1 - Sep 2

Kitchen features a refrigerator, microwave, oven, and sink with a faucet, along with a dining area and wooden cabinets.

"Cozy accommodations, great location, beautiful property, wonderful hosts."

Relax in this inviting living room with a stone fireplace, large windows, and comfortable seating.

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

Cozy space with a high ceiling and exposed beams, featuring a dining area with a round table and chairs.

"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"