Chesapeake City Cottages

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

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Our top choices for Chesapeake City cottages

A wooden deck with a hot tub, lounge chairs, and a view of the water.

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

Charlestown

Mike F.

includes taxes & fees

22 Sept - 23 Sept

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

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

Lincoln University

Arthur B.

includes taxes & fees

9 Sept - 10 Sept

A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

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

Port Deposit

Terry R S.

includes taxes & fees

7 Sept - 8 Sept

A residential area with houses, a parking lot, and a body of water in the background.

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

Port Deposit

jerel p.

includes taxes & fees

9 Sept - 10 Sept

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Top Chesapeake City Hotel Reviews

Embassy Suites by Hilton Newark Wilmington South

10/10 Excellent

"Omg this place!!!! Everything I needed and wanted, I visit plenty of hotels and this one I didn’t want to leave. I am definitely coming back just because…💕💕🚨"

HYDRANGEA HOUSE Waterview cozy 3-bdrm Getaway in quiet Chesapeake City AC & yard

10/10 Excellent

"Cute place, great location!The owner told us we were the first booking since she purchased the home! It was perfect for my stay, located right by the C&D Canal, the Recreation Trail (and the bike rentals were right there!) and we walked to Schaefer’s for a sunset cocktail. I had some questions for the owner, who was super nice and responsive. We had Wi-Fi, TV, washer/dryer, great kitchen appliances, and the rooms were clean, neat and nicely decorated. The owner has clearly done some recent renovations which were great, and she told me more renovations were on the way. I’ll be rolling through here a few times a year and I found my new spot – highly recommend!"

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