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.
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.
"This is a beautiful hotel. We were given a room with a balcony. Gorgeous view of the bay. Lovely watching the sunset and then sunrise from the balcony. The room was clean. Bed comfortable. For the price would've been nice to have breakfast included but that's minor. "
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
10/10 Excellent
"After driving for 500 miles I just needed a place to stop. I didn't need fancy amenities or anything else just a place to sleep for the night and this was perfect and the price reasonable. A good sized clean room with a soft bed and a hot shower is not too much to ask for but so many hotels miss the mark. This one didn't"
The Inn at Henderson's Wharf, Ascend Hotel Collection
10/10 Excellent
"Loved walking into the beautifully decorated lobby. Eric greeted us, although our room wasnt quite ready at check-in we were able to relax with a fresh baked cookie and iced tea. There was also coffee and tea available as well. Our room was upgraded to a pier/water view which did not disappoint. We found Scrabble in the lobby and enjoyed a glass of wine. This property had a fun history and is walking distance to Fells Point with many shops and restaurants.
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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?
Where can I get free parking with my stay in Chestertown?
These hotels offer the perk of free parking: Driftwood Inn, Red Roof Inn & Suites Chestertown and Comfort Inn & Suites Chestertown. There are 5 options you may want to check out on our site.
Can I book a refundable hotel 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 should I consider staying in Chestertown if I'm looking for a cheap accommodation?
Two inexpensive options worth considering are Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.
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 24 vacation homes. In addition, you can choose from 9 apartments.
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.
