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

Search Chesapeake City Cottage Rentals from CA $289

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four 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, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is CA $438
CA $690 total
includes taxes & fees
Sep 13 - Sep 14
Long Beach Cottage, (romantic couple’s getaway)
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

2. 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, (52 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is CA $242
CA $289 total
includes taxes & fees
Sep 10 - Sep 11
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is CA $306
CA $706 total
includes taxes & fees
Sep 15 - Sep 16
Thunder Hill Retreat - Spacious/Deck/Hot tub
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

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (15 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is CA $277
CA $408 total
includes taxes & fees
Sep 21 - Sep 22
Quarry Landing - Center of Town & River View - 3 Bedroom
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake City Hotel Reviews

Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

10/10 Excellent
"The rooms were very clean and comfortable bed! Bathroom had everything you needed for your stay. The lobby and dining area small but comfortable. Fireplace near. Breakfast was ok,everyone seemed to be enjoy and the staff was ever so pleasant. Check in easy breezy no issues whatsoever! Would definitely stay here again on my next visit to Delaware."
michelle 1-night trip
Posted 15 hours ago
Comfort Inn & Suites Newark - Wilmington

Find out more about Chesapeake City

Chesapeake City Cottages information

Number of reviews
82
Accommodation
28 Cottages
Lowest Price
CA $289
Highest Price
CA $706

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.

Explore a world of travel with Expedia