Compare Chesapeake City Vacation Rentals

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Chesapeake City Rentals

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

6.08 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

0.42 mi from city center
At this vacation home, guests have access to features like an arcade/game room and laundry facilities.
Historic Chesapeake City Stay

Historic Chesapeake City Stay

0.18 mi from city center
$265 nightly
The price is $281 total per night
$281 total
Jul 11 - Jul 12
Total includes taxes and fees
This cabin is a smoke-free cabin.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cabin close to Fair Hill on horse farm

3.92 mi from city center
$608 nightly
The price is $644 total per night
$644 total
Jul 14 - Jul 15
Total includes taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

2.95 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

3.21 mi from city center
At this vacation home, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

9.16 mi from city center
At this cabin, guests have access to a hot tub, laundry facilities, and local meal delivery service. Additional amenities include barbecue grills and a garden.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10.93 mi from city center
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

10.45 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

14.94 mi from city center
At this houseboat, guests have access to features like laundry facilities. This smoke-free houseboat also has barbecue grills.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

18.21 mi from city center
$215 nightly
The price is $228 total per night
$228 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests staying at this cottage enjoy features like a water park.
Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

19.47 mi from city center
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills.
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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.

How to Book Vacation Rentals in Chesapeake City



🏠 What is the best price for Chesapeake City vacation rentals?

Chesapeake City vacation rentals range in price, starting at $228 per night.


🏠 What types of vacation rentals in Chesapeake City can I rent?

Orbitz offers a wide range of Chesapeake City rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chesapeake City condo rentals.


🏠 Is it free to cancel my Chesapeake City vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chesapeake City vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chesapeake City. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chesapeake City?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chesapeake City apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chesapeake City?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chesapeake City package deals will get you even more savings.

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