Photo by Julie Miller

Hotels in Chestertown

your current months are January, 2025 and February, 2025.
January 2025
February 2025

Find and book your perfect stay

Earn rewards on every night you stay
Save more with Member Prices
Free cancellation options if plans change

Where to stay in Chestertown?

Friends Lake Inn
Premier Room

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (84)
The price is CA $321
CA $357 total
includes taxes & fees
Dec 29 - Dec 30
Friends Lake Inn
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.

Top landmarks in Chestertown

Friends Lake

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.

See properties in Friends Lake
Friends Lake

Learn more about Chestertown

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.

See all hotels in Chestertown
Photo by Julie Miller
Open Photo by Julie Miller

Frequently asked questions

Where can I find free parking with my stay in Chestertown?
Park your car for free at The Loft at The Remington.
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 with my pet in Chestertown?
Your furry friend can stay with you at these pet-friendly hotels: Pine Tree Motel & Cabins, Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing and Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
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 8 apartments and 7 condos.
Where can I stay if I'm traveling to Chestertown with my kids?
Parents traveling with children may want to consider Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
Where should I stay in Chestertown for a vacation with my partner?
Friends Lake Inn and The Fern Lodge are great options for a romantic getaway.
Where should I stay in Chestertown if I want a luxury hotel?
An option for a luxury stay is Friends Lake Inn.
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.