Find Hotels with Restaurants in Chestertown, MD

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Check availability on Chestertown Hotels with Restaurants

Tonight
Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Top Chestertown Hotels with Restaurants

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

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 9 - Dec 10
Total with taxes and fees
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (860)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
$93 nightly
The price is $103
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown
Lobby
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, (1001)
"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
$84 nightly
The price is $94
Dec 28 - Dec 29
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby lounge
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
$84 nightly
The price is $94
Dec 23 - Dec 24
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (631)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
$87 nightly
The price is $97
Dec 18 - Dec 19
Total with taxes and fees
Hilton Garden Inn Aberdeen
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (673)
"Great view, good ambiance all around"
United States
Dianne
$116 nightly
The price is $129
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Front of property - evening/night
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, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
$207 nightly
The price is $230
Dec 14 - Dec 15
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Reception
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
$90 nightly
The price is $101
Jan 8 - Jan 9, 2026
Total with taxes and fees
Hilton Garden Inn Bel Air
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (809)
"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
$78 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
Comfort Inn & Suites Aberdeen near APG
Premium bedding, in-room safe, desk, iron/ironing board
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 view from our room of the Cal Ripkin complex was amazing. "
United States
Christopher
$101 nightly
The price is $113
Dec 29 - Dec 30
Total with taxes and fees
Residence Inn Aberdeen at Ripken Stadium
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The room was exll"
Anthony 1-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh

Frequently asked questions

How much do hotels with dining in Chestertown cost?
You can expect to pay between $87 and $230 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 dining in Chestertown with Expedia?
Reserving a hotel with dining 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 dining in Chestertown?
With Expedia's nifty filter tool, getting your hands on cheap hotels with dining 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 dining?
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.

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