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.
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You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
Wander cobblestone streets lined with 18th-century buildings, soaking in the colonial atmosphere of this historic Chesapeake Bay town. Sail the Chester River on a traditional skipjack, then browse antique shops and art galleries along High Street.
The town is absolutely charming, a cozy little jewel of the Chesapeake. The Tea Party is underrated, a definite must do for Memorial Day weekend. The fair is fraught with great food, drink, entertainment, and of course, the A+ colonial swashbuckling.
Cynthia
8.0/10
Good
Downtown is quite charming & well-to-do looking - lots of quaint shops & handsome historic houses. Short walk to the river & a short scenic walk there. Shopping areas on northern outskirts are a different story - lots of vacancies & decline.
John
8.0/10
Good
Chestertown is a nice town to raise a family. I would live in the outskirts but that is a personal preference. It is a nice college town.
"The location was wonderful. The hotel is quaint and a lovely place to stay. I only interacted with the front desk staff but she was very kind. I’m excited to come back. "
"Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site. "
The Inn at Henderson's Wharf, Ascend Hotel Collection
10/10 Excellent
"I loved room 121. It was a beautiful architecture and view. Very quiet and comfortable. The hosts were super friendly, offered us a check in drink, but I was almost late for my BYOB Urban Pirate cruise, so I had to decline. There is a bakery right around the corner, and lots of great food and shopping to walk to. I was there to enjoy the old town walks and shops and I sure did!"
You can find top hotels in Chestertown from $51 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?
It's easy to book a refundable Chestertown hotel on Hotels.com. Simply 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 the top Chestertown hotels with a pool?
Discover some of the best Chestertown hotels with a pool for a little extra luxury on your trip. The Lodge at Great Oak Landing is a great lodge with a seasonal outdoor pool and a guest rating of 8 out of 10. Plus, you can make the most of its private beach (direct access) and restaurant. You can select "Pool" in the "Amenities" filter of your search on Hotels.com to find even more places to stay in Chestertown with a pool.
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:
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 hotels do travelers recommend in Chestertown?
If you're looking for the flexibility to change your plans to Chestertown, most properties offer refundable* rates you can book. You can find these properties 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 animal companion is welcome at these pet-friendly hotels: Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, and Driftwood Inn.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 25 vacation homes. In addition, you can choose from 9 apartments.
Where can I stay if I'm visiting Chestertown with my kids?
Parents traveling with children may want to consider Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.
Where should I stay in Chestertown for a getaway with my partner?
Red Roof Inn & Suites Chestertown is a great option for a romantic getaway.
Find out more about Chestertown
Find out more about Chestertown
If you're looking for a place to get away, 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.
