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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

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)

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 CA $424
CA $643 total
includes taxes & fees
Nov 9 - Nov 10
Long Beach Cottage, (romantic couple’s getaway)
A residential area with houses, a parking lot, and a body of water in the background.

2. 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, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is CA $209
CA $314 total
includes taxes & fees
Nov 22 - Nov 23
Quarry Landing - Center of Town & River View - 3 Bedroom
A two-story house with a deck, a barbecue grill, and a covered patio area.

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

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (25 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is CA $329
CA $678 total
includes taxes & fees
Nov 9 - Nov 10
Thunder Hill Retreat - Spacious/Deck/Hot tub
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
9.8 out of 10, Exceptional, (60 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is CA $276
CA $314 total
includes taxes & fees
Nov 10 - Nov 11
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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Learn more about Chesapeake City

This charming canal town offers waterfront dining where you can watch massive ships pass surprisingly close to shore. Explore the C&D Canal Museum to understand Chesapeake City's maritime history, then stroll across the bridge for spectacular views at sunset.

See all hotels in Chesapeake City
A river with a bridge, marina, and residential area.

Top reviews in Chesapeake City

A modern building with a covered entrance, stone pillars, and a parking lot with cars.
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
Middletown

10/10 Excellent

Clean and conveniently located.
Canada
Cat
Reviewed August 28, 2026
Holiday Inn Express & Suites Middletown by IHG

Frequently Asked Questions

Why book your cottage in Chesapeake City with Expedia?

Booking a cottage in Chesapeake City is as easy as working out your travel dates and selecting your ideal place for a vacation in nature. From upmarket retreats to budget-friendly stays and cottages that include amenities like a kitchenette, Expedia has something for all traveler tastes. As for epic deals? We've got them too!

How can I find cheap cottages in Chesapeake City?

With Expedia's filter tool, comparing cheap cottages in Chesapeake City is easy. To find properties that are friendly on the wallet, fine-tune your search results by budget, star rating and amenities.

What is there to do in Chesapeake City near my cottage?

The perfect travel accessory is a well-planned schedule. Bohemia Vista Marina is an excellent place to kick-start your adventures in Chesapeake City.

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