Search Chesapeake City Cottage Rentals from CA $209

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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 $467
CA $692 total
includes taxes & fees
Nov 17 - Nov 18
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 28 - Nov 29
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 $709 total
includes taxes & fees
Nov 16 - Nov 17
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 Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown

10/10 Excellent

Amazing experience! Great customer service 10/10
Canada
DISHANT
Reviewed September 21, 2024
Fairfield Inn & Suites by Marriott Middletown

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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