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.
Go beyond your typical stay in Chestertown
Our prices for Chestertown are cheapest in October
Our prices for Chestertown are cheapest in October
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.
Check out reviews of Chestertown hotels guests love
The Queensbury Hotel
10/10 Excellent
"The property was very nice. It was quiet and very clean. The restaurant was very good and the service was amazing. The pool was a little to cold for swimming as it was a cooler day and there was a lot of chlorine in it. "
"Clean enough for 1 night stay, rooms were old but in ok conditions, no breakfast coffee only in certain times, lobby doesn’t look like the listing (see photos attached) feels a bit like an abandoned overall property … pool closed"
Clarion Inn & Suites at the Outlets of Lake George
10/10 Excellent
"Very good Hotel, confortable bed, clean room, good breakfast, David check carefully to be sure that nothing is missing. The only thing , balcony needs to be paint. "
You can find top hotels in Chestertown from $46 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com, and sort hotels by "Price: low to high". If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Chestertown hotels?
Members can save up to 20% on select hotels in Chestertown. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.
Can I book Chestertown hotels with free cancellation?
To book a refundable Chestertown hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best hotels in Chestertown for couples?
Choose a top-rated Chestertown romantic hotel and enjoy your couple's getaway. Our travelers love Friends Lake Inn, a hotel with a restaurant as well as in-room champagne service. Another romantic hotel with top reviews is The Fern Lodge. This bed & breakfast offers a private hot tub and an in-room fireplace for a perfect stay. Discover more hotels in Chestertown on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".
What are some of the best Chestertown hotels with free parking?
If you're arriving by car, choosing a great Chestertown hotel with free parking is a plus. Our travelers' favorites include:
The Fern Lodge: A bed & breakfast with an average guest rating of 9.8 out of 10
What are some popular hotels in central Chestertown?
If you're looking for hotels in central Chestertown, check out Friends Lake Inn. Travelers love Friends Lake Inn for its location, as well as the restaurant, bar/lounge and couples/private dining this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.
Are all taxes and fees included in the Chestertown hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
What accommodations do travelers like in Chestertown?
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 60 vacation homes. In addition, there are 7 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.
