Photo by Julie Miller

Chestertown cottages

We found 16 cottages — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any cottage rentals in Chestertown?
Select one of our 16 cottage rentals in Chestertown and get set to enjoy the charm, comfort and unique experiences that come with this type of escape. Town of Horicon, Little Gore Glades and Sagamore Glades are some of the city's most sought-after areas.
How much does it cost to stay in a cottage rental in Chestertown?
Scroll through our cottage rental listings in Chestertown for a good idea of costs. If you want to save, try our "Discounts" filter. It'll reveal any cottages featuring special promotions, whether that's a weekly, monthly or new listing discount.
When is the best time to rent a cottage in Chestertown?
Consider visiting Chestertown in July, when the average daily temperature ranges between 13ºC (55ºF) and 27ºC (81ºF). This is the most popular time for Vrbo guests to book a homey cottage rental in this destination, which is located in Warren County.
Where can I rent a Chestertown holiday cottage with great views?
Cottages with views of historic areas are just one of the types of cottage rentals available in Chestertown. If you're looking for stays that boast vistas worth writing home about, Vrbo can help you find them.
Does Chestertown have any lakeside cottages?
Wake up to beautiful scenery in the morning and fall asleep to the peaceful sounds of nature at night in one of Vrbo's lakeside cottage rentals. Add some outdoor activities in the daytime and you've got yourself the ideal holiday by the water. To see if there are any lakeside cottages in Chestertown, make use of our "Location" filter and then select "Lake."
What are the top things to do in Chestertown?
Get your Chestertown escape off to an awesome start with a visit to top attractions like Lake George, Gore Mountain Ski Resort and Loon Lake Beach. Stay in a Vrbo cottage rental with the family and then explore the best of this destination together.
Why should I book my holiday cottage with Vrbo?
Whether in the countryside or next to rolling waves, Vrbo's cottage rentals will put you exactly where you'd like to be. Finding your dream stay is a cinch when you use our filters to browse by things like nearby attractions, amenities and budget. Besides getting the entire cottage rental to yourselves, our cancellation policies take the hassle out of booking. Additionally, our One Key™ loyalty programme allows you to collect and use OneKeyCash™* on all eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.