Compare Chesapeake City Vacation Rentals

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Chesapeake City Rentals

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

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

Chesapeake City MD
0.07 mi from city center
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!

Chesapeake City MD
0.33 mi from city center
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City MD
0.5 mi from city center
Guests of this vacation home have access to an outdoor pool, a gym, and a hot tub. Additional amenities include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City MD
0.18 mi from city center
$280 nightly
The price is $297 total per night
$297 total
Aug 9 - Aug 10
Total with taxes and fees
This cabin is a smoke-free cabin.
Kitchen
Free WiFi
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

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

Chesapeake City MD
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.
Kitchen
Washer
Hook Wine & Sinker~sleeps 14 to 16 water views!!!

Hook Wine & Sinker~sleeps 14 to 16 water views!!!

Chesapeake City MD
0.42 mi from city center
At this vacation home, guests have access to features like an arcade/game room and laundry facilities.
Kitchen
Washer
Sunset River Cottage

Sunset River Cottage

Elkton MD
2.98 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.
Hot Tub
Kitchen
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD
10.93 mi from city center
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charlestown MD
9.6 mi from city center
At this cottage, guests have access to barbecue grills.
Washer
Dryer
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

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

Perryville MD
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.
Hot Tub
Kitchen
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.

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.
Kitchen
Washer
Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC

Darlington MD
22.29 mi from city center
$168 nightly
The price is $178 total per night
$178 total
Aug 3 - Aug 4
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
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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.

Chesapeake City Large Group Rentals

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 $178 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.