Search Hotels with Restaurant in Chestertown

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Check availability on Chestertown Hotels with Restaurant

Our top choices for Chestertown hotels with a restaurant

Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is 2.604.393 ₫
2.977.602 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is 2.441.290 ₫
2.709.621 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hampton Inn Middletown
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (632)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
The price is 2.207.947 ₫
2.472.901 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Aberdeen
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1004)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
The price is 2.185.586 ₫
2.447.858 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Friendly staff, clean hotel "
United States
Kelly
The price is 2.357.107 ₫
2.639.959 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Hilton Garden Inn Bel Air
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is 2.893.770 ₫
3.212.084 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hyatt Place Kent Narrows & Marina
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (216)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is 2.213.734 ₫
2.479.382 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Courtyard Aberdeen at Ripken Stadium
Premium bedding, in-room safe, desk, iron/ironing board
Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (106)
"The stay was perfect everyone was super kind and helpful and I will definitely be back "
United States
Katlynn
The price is 2.660.953 ₫
2.980.267 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Residence Inn Aberdeen at Ripken Stadium
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
7.8 out of 10, Good, (811)
"I love this property very quiet and it's convenient to the shopping center and if you want other food it's connected to an IHOP you don't have to go out in the elements "
United States
Shelia
The price is 2.026.954 ₫
2.270.188 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn & Suites Aberdeen near APG
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (430)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is 4.836.426 ₫
6.037.682 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Inn at Chesapeake Bay Beach Club
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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Top Chestertown Hotel Reviews

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Frequently asked questions

How much do hotels with dining in Chestertown cost?
You can expect to pay between 2.447.858 ₫ and 11.220.725 ₫ per night for hotels in Chestertown. An ideal stay with a restaurant, or one that's near some great foodie experiences, is waiting for you with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with dining in Chestertown?
Consider Comfort Inn & Suites Chestertown — a 2.5-star option not far from downtown Chestertown. This family-friendly hotel with dining has convenient amenities like complimentary breakfast and housekeeping services. Once you've checked in and dropped off your luggage, there's no shortage of family-friendly attractions to discover in and around Chestertown. Historical Society of Kent County Maryland and River Arts Chestertown are two popular options.
Why book your hotel with restaurants in Chestertown with Expedia?
Reserving a hotel with restaurants in Chestertown is as easy as entering your travel dates and picking a place suited to your needs. Chasing a stay that has an on-site restaurant or is near a food hub? Want it to be upscale or budget friendly? Use Expedia's filters to narrow your results even further and find the ideal fit at the right price.
How can I find cheap hotels with restaurants in Chestertown?
With Expedia's nifty filter tool, getting your hands on cheap hotels with restaurants in Chestertown is a breeze. To discover properties that are easy on the wallet, refine your search by meal plans, budget and star rating.
What is there to do in Chestertown near my hotel with restaurants?
After you've checked in to your hotel, set out and explore the fun things Chestertown has to offer. Historical Society of Kent County Maryland is one attraction to add to your must-see list.