Search Resort Hotels in Chestertown from CA $76

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Recommended hotels in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (872 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is CA $139
CA $154 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is CA $148
CA $169 total
includes taxes & fees
Mar 2 - Mar 3
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is CA $98
CA $109 total
includes taxes & fees
Feb 13 - Feb 14
Red Roof Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is CA $135
CA $217 total
includes taxes & fees
Feb 9 - Feb 10
First Floor Studio Apartment in Historic Chestertown

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
The price is CA $343
CA $577 total
includes taxes & fees
Feb 21 - Feb 22
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

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, (1,001 reviews)
"Everything was great"
United States
juan
The price is CA $117
CA $132 total
includes taxes & fees
Feb 15 - Feb 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (310 reviews)
"Always consistent and great staff!"
United States
Linda
The price is CA $150
CA $168 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites by Marriott Aberdeen

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, (660 reviews)
"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"
United States
Valerie
The price is CA $148
CA $164 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express & Suites Middletown by IHG

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, (1,001 reviews)
"We always enjoy our stay here when visiting our family as the facility is clean, comfortable and quiet. Only exception was on one of the days a fire alarm had gone off and scared us awake but it turned out to be a false alarm. "
United States
Cheryle
The price is CA $109
CA $122 total
includes taxes & fees
Mar 1 - Mar 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"Great stay"
United States
Edward
The price is CA $98
CA $109 total
includes taxes & fees
Feb 16 - Feb 17
Quality Inn Smyrna

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,006 reviews)
"Great stay as always"
United States
Linda
The price is CA $111
CA $124 total
includes taxes & fees
Feb 12 - Feb 13
Hampton Inn & Suites Edgewood/Aberdeen-South

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is CA $164
CA $230 total
includes taxes & fees
Feb 11 - Feb 12
Kent Island Resort

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, (481 reviews)
"The staff is great, roon clean & spacious"
United States
Thomas
The price is CA $115
CA $129 total
includes taxes & fees
Feb 9 - Feb 10
Candlewood Suites Aberdeen-Bel Air by IHG

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (242 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is CA $139
CA $156 total
includes taxes & fees
Feb 13 - Feb 14
Hilton Garden Inn Bel Air

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (103 reviews)
"Clean room and attentive staff ."
United States
Stephen
The price is CA $181
CA $202 total
includes taxes & fees
Feb 8 - Feb 9
TownePlace Suites by Marriott Edgewood Aberdeen

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, (344 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
The price is CA $128
CA $143 total
includes taxes & fees
Feb 13 - Feb 14
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (342 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is CA $135
CA $150 total
includes taxes & fees
Feb 15 - Feb 16
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (958 reviews)
"Lovely location"
United States
Cheryl
The price is CA $139
CA $154 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Express Annapolis East-Kent Island by IHG

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.4 out of 10, Good, (10 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
The price is CA $68
CA $76 total
includes taxes & fees
Mar 2 - Mar 3
Motel Edgewood

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
"Nice staff and rooms"
United States
Walter
The price is CA $117
CA $129 total
includes taxes & fees
Mar 4 - Mar 5
Quality Inn Grasonville near Kent Island
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

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
9,936
Accommodation
0 Resorts
Lowest Price
CA $76
Highest Price
CA $577

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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