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Chester Winter Rentals & Holiday Homes

Discover winter rentals Chester - We found 30 exact matches

About Chester Winter Rental on Varoom

Planning on a winter vacation and need a place to stay in Chester? Discover 30 places to stay in Chester, for those traveling with their family, friends, or in large groups.

At Varoom, we feature a wide range of listings for accommodations in Chester, NY that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. Varoom winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow, or running to it, Varoom can connect you to the best cabins, bungalows, and rent by owner homes as well as best places to stay in both sun and ski resorts. Varoom will make your winter trip memorable.

Varoom offers a great deal for travelers planning on renting a place in Chester, to enjoy these benefits and to book your winter vacation homes, go to Varoom filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Chester and unlock even more amazing deals.

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Frequently Asked Questions About Chester Winter Rentals

There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Chester:

The average cost for winter rentals in Chester is $929 per night. Varoom has a wide list of great winter places to stay near Chester that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Chester that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Chester on Varoom

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chester to find what works for you.
As of 2025, the data from Varoom shows that there are over 30 private swimming pools or indoor pools accommodations near Chester along with other great amenities.

About 30 holiday rentals in Chester boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Chester for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Chester with all the best amenities for your next trip.