A river with a bridge, marina, and residential area.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chesapeake City cottages

A two-story house with a deck, a barbecue grill, and a covered patio area.

1. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
Thunder Hill Retreat - Spacious/Deck/Hot tub
A wooden deck with a hot tub, lounge chairs, and a view of the water.

2. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is AED 1,349
AED 2,031 total
includes taxes & fees
22 Oct - 23 Oct
Long Beach Cottage, (romantic couple’s getaway)
A residential area with houses, a parking lot, and a body of water in the background.

3. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (17 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
Quarry Landing - Center of Town & River View - 3 Bedroom
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

4. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.6 out of 10, Exceptional, (55 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is AED 645
AED 777 total
includes taxes & fees
4 Oct - 5 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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 Chesapeake City Hotel Reviews

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