Chestertown Historic District Tours

Plan a trip to see Chestertown Historic District

Price found within the past 48 hours. Click for updated prices.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $575, price is now $521 per person
$521
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.8/10 Excellent! (1,036 reviews)
The Americana was the perfect hotel for our weekend at Oceans calling. It was far enough away from the action to be quiet but also very accessible. Parking was great as was the ocean view. Would stay again

Reviewed on Sep 29, 2025

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Price was $799, price is now $676 per person
$676
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (756 reviews)
Bugs on window sill in dining area. Grease trap on sidewalk was leaking. All other public areas were EXCELLENT. Housekeeping could have cleaned the toilet . Greeter in load/unload area was very helpful and pleasant. I think his name was Olem. Front desk staff was pleasant and friendly and knowledgeable. Overall we have no complaints. We had a pleasant stay.

Reviewed on Oct 1, 2025

Holiday Inn Express Hotel & Suites Salisbury - Delmar by IHG

Holiday Inn Express Hotel & Suites Salisbury - Delmar by IHG

2.5 out of 5
Price was $752, price is now $691 per person
$691
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.2/10 Very Good! (814 reviews)
Very friendly staff. Unfortunately the sofa bed mattress pad was soiled and dirty. There were no pillows or sheets for it. Otherwise everything else was very nice.

Reviewed on Sep 21, 2025

Popular places to visit

Garfield Center for the Arts at the Prince Theater

You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Garfield Center for the Arts at the Prince Theater

Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.

Sumner Hall

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

Kings Town Park

Best Lodging Options Near Chestertown Historic District

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Hyatt Place Kent Narrows & Marina
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

2.5 out of 5
6110 Greenleigh Avenue, Middle River, MD
SpringHill Suites Baltimore White Marsh/Middle River
Quality Inn & Suites Bel Air I-95 Exit 77A

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

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Quality Inn & Suites Bel Air I-95 Exit 77A
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road, Stevensville, MD
The Inn at Chesapeake Bay Beach Club
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

2.5 out of 5
1807 Edgewood Rd, Edgewood, MD
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
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 out of 5
2112b Emmorton Park Rd, Edgewood, MD
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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

3 out of 5
1435 Handlir Dr, Bel Air, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 out of 5
2110 Emmorton Park Rd, Edgewood, MD
Hampton Inn & Suites Edgewood/Aberdeen-South
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3 out of 5
793 W Bel Air Ave, Aberdeen, MD
La Quinta Inn & Suites by Wyndham Aberdeen-APG
See all 2,126 properties in Chestertown Historic District
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.