Chestertown house rentals

Choose from 234 holiday home rentals in Chestertown that have more privacy, space, amenities and value compared to a standard hotel room. Consider houses in sought-after areas such as Town of Horicon, Little Gore Glades and Sagamore Glades.

Prices vary according to length of stay, season and specific location, so enter your trip details to check out what’s available. No matter your budget or plans, Stayz has holiday home rentals in Chestertown for every type of guest.

That can all depend on the weather conditions you like most, among other considerations. Many visitors to Warren County book a Chestertown holiday home rental in July, when average temperatures range from 13ºC to 27ºC.

If your idea of a dream getaway is one enjoying beautiful vistas without leaving the property, we’ll help you find a holiday home rental you’ll love. Into views of historic areas? Stayz has houses in Chestertown that come with just that.

Some of our holiday houses are available for weekend rental, making them ideal for impulsive getaways. Enter your desired travel dates to check out the availability. You may need to switch up the dates and be flexible with your plans to find the best holiday home rental in Chestertown.

With seven pet-friendly holiday home rentals in Chestertown, you can plan your next trip with your four-legged companion right by your side. On top of a comfortable bed for everyone, plenty of houses also come with features like fenced-in yards and complimentary dog treats. See what’s available by clicking on the “Pets allowed” filter.

It’s easy to see why families love Chestertown, with top attractions like Lake George, Gore Mountain Ski Resort and Loon Lake Beach to explore. Check out this destination’s best sights together and then return to the comforts of your holiday home rental.

Booking your holiday home rental with Stayz means you’ll have the entire place to yourselves — your private oasis, without any interruptions or distractions from anybody else. Also, our flexible payment and cancellation policies give you the freedom to amend your plans if necessary.