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Recommended hotels in Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.2 out of 10, Very good, (61)
"Great place to get some quiet rest by the water"
The price is CA $183
CA $203 total
includes taxes & fees
Aug 19 - Aug 20
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (794)
"It was a clean comfortable spot to rest for the night. "
The price is CA $157
CA $175 total
includes taxes & fees
Aug 24 - Aug 25
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (386)
"Good location."
The price is CA $99
CA $110 total
includes taxes & fees
Aug 24 - Aug 25
Red Roof Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (98)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is CA $124
CA $206 total
includes taxes & fees
Aug 20 - Aug 21
First Floor Studio Apartment in Historic Chestertown

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Wonerful place, all good..Hotel,area, staff."
The price is CA $123
CA $136 total
includes taxes & fees
Sep 17 - Sep 18
Quality Inn

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (86)
"Owner was very nice. "
The price is CA $123
CA $137 total
includes taxes & fees
Aug 19 - Aug 20
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (820)
"Front desk service was exceptional!!"
The price is CA $152
CA $168 total
includes taxes & fees
Aug 24 - Aug 25
Hampton Inn Middletown

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (604)
"Very beautiful and clean properly with great staff. "
The price is CA $160
CA $178 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express & Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (261)
"Nice place to stay"
The price is CA $142
CA $158 total
includes taxes & fees
Sep 8 - Sep 9
Fairfield Inn & Suites by Marriott Middletown

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Very beautiful with private waterfront. Roomy and clean. Like another world away ."
The price is CA $496
CA $892 total
includes taxes & fees
Sep 1 - Sep 2
5-bedroom vacation home 5 minutes from historic Charlestown

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $345
CA $579 total
includes taxes & fees
Aug 19 - Aug 20
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Quality Inn

2.5 star property
7.8 out of 10, Good, (810)
"Conveniently located with overall great value."
The price is CA $135
CA $150 total
includes taxes & fees
Sep 14 - Sep 15
Quality Inn

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Staff was very friendly. We had a very relaxing stay. "
The price is CA $204
CA $229 total
includes taxes & fees
Sep 17 - Sep 18
Vandiver Inn

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.6 out of 10, (942)
"Front desk lady was super friendly helpfull dollor general close clean room great value"
The price is CA $73
CA $82 total
includes taxes & fees
Aug 24 - Aug 25
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (984)
"Great spot with beautiful views. "
The price is CA $218
CA $242 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (887)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is CA $181
CA $201 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1003)
"Excellent location"
The price is CA $150
CA $167 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (608)
"Great place to stay. "
The price is CA $234
CA $259 total
includes taxes & fees
Sep 15 - Sep 16
Hyatt Place Kent Narrows & Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (34)
"We really enjoyed our stay. Looking forward to staying again!"
The price is CA $152
CA $387 total
includes taxes & fees
Sep 7 - Sep 8
Cass-N-Reel Luxury Houseboat

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
The price is CA $221
CA $246 total
includes taxes & fees
Aug 19 - Aug 20
Inn at Huntingfield Creek
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