Best Resorts in Chestertown

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In two weeks
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Jan 23 - Jan 25
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Feb 20 - Feb 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Free daily full breakfast
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (861)
"Everything was well!"
United States
Ahmed
$104 nightly
The price is $115
Dec 29 - Dec 30
Total with taxes and fees
Comfort Inn & Suites Chestertown
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
$113 nightly
The price is $126
Dec 24 - Dec 25
Total with taxes and fees
The Lodge at Great Oak Landing
Lobby lounge
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (421)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
$72 nightly
The price is $80
Dec 29 - Dec 30
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 24 - Dec 25
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Property amenity
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (323)
"The room was spotless, courteous staff, and a wonderful breakfast to start my day "
United States
Alan
$108 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | Free WiFi, bed sheets
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very Good, (1006)
"Very good hotel for the price clean and comfortable "
Canada
Randy
$69 nightly
The price is $77
Dec 24 - Dec 25
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Desk, laptop workspace, iron/ironing board, free WiFi
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1002)
"Very pleasant experience. "
United States
Kathleen
$69 nightly
The price is $76
Jan 22 - Jan 23, 2026
Total with taxes and fees
Quality Inn Smyrna
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (651)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
$94 nightly
The price is $104
Jan 23 - Jan 24, 2026
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (338)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
$71 nightly
The price is $80
Jan 10 - Jan 11, 2026
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (866)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
$95 nightly
The price is $106
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (95)
"Spotless, very good "
United States
Efrain
$109 nightly
The price is $122
Dec 24 - Dec 25
Total with taxes and fees
TownePlace Suites by Marriott Edgewood 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, (1003)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
$79 nightly
The price is $89
Jan 13 - Jan 14, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (604)
"very pet friendly!!"
United States
larry
$98 nightly
The price is $110
Jan 9 - Jan 10, 2026
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (471)
"Staff was super friendly, room was above expectations"
United States
Thomas
$83 nightly
The price is $93
Dec 26 - Dec 27
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG
Free daily continental breakfast
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1010)
"Room was very nice. Staff is always very nice."
United States
Peggy
$59 nightly
The price is $67
Dec 24 - Dec 25
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1002)
"Nice place"
United States
Maria
$89 nightly
The price is $100
Dec 30 - Dec 31
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Restaurant
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, (217)
"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
Jan 8 - Jan 9, 2026
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (562)
"This is my forth time at this hotel. Excellent service . Not staying for breakfast but usually very good"
United States
Carolyn
$82 nightly
The price is $92
Dec 26 - Dec 27
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Bar (on property)
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, (231)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
$98 nightly
The price is $109
Jan 9 - Jan 10, 2026
Total with taxes and fees
Hilton Garden Inn Bel Air
Reception
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1007)
"Room was great staff friendly"
United States
Melissa
$84 nightly
The price is $94
Dec 29 - Dec 30
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Lovely hotel, my favorite place to stay in Annapolis!"
Mary Ann 1-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
11,823
Accommodation
0 Resorts
Lowest Price
$67
Highest Price
$159

Frequently asked questions

What is Chestertown like for a resort vacation?
Longing for a relaxing escape? Indulge in all the luxuries and comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to entertainment and shopping. Browse the resorts in the area and discover the right one for you, whether you see yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What can I do in Chestertown?
Check out the interesting exhibits at Historical Society of Kent County Maryland, or bring the kids to Crumpton Auction for some family fun. For more to see in the area, you can spend time at Northern Chesapeake Bay or Chesapeake Bay.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's the best way to get to and around Chestertown?
Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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