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.
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.
Commune with nature and explore the great outdoors at Tripp Pond during your travels in Chestertown. While you're in the area, stroll along the lakeside.
Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.
"The pool is great for the kids, the breakfast and lunch at the bar are good and they don’t break the bank. Being able to walk down to the water and not worry about the kids terribly is always a plus. We love it. Hidden gem. "
"We stayed 5 days family trip . Everything was awesome. The staff were very polite, friendly and helpful. Will definitely stay here again. We stayed in a 3 queen bed room. Beds were comfy, room was clean, no issues. They have washer/ dryer that uses quarters that you can purchase from receptionist which came in really handy. The indoor pool is a plus. We had a rainy day and the children were still entertained. The breakfast was very good. The first day was very packed but still enough food for all just a bit of a wait for the waffle maker. Location is great less than 10 minute drive to everything. Lots to do in the area. My family had a wonderful time. "
Can I book a refundable accommodation in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, look over our selection of 62 vacation homes. In addition, there are 8 apartments and 7 condos.
What will the weather in Chestertown be like during my visit?
The warmest months in Chestertown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are June and July.
Why should I book my Chestertown hotel with Hotels.com?
There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
Find out more about Chestertown
Find out more about Chestertown
If you're looking to discover somewhere new, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.
