Compare Chesapeake Beach Vacation Rentals

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Chesapeake Beach Rentals

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

1.01 mi from city center
Guests staying at this vacation home have access to barbecue grills and a garden.
Kitchen
Air conditioning
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

3.37 mi from city center
This vacation home offers an outdoor pool, a sauna, and a hot tub. Additional amenities include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

12.01 mi from city center
At this cabin, guests have access to a garden.
Pool
Kitchen
Waterfront Camper with Dock

Waterfront Camper with Dock

13.29 mi from city center
$316 nightly
The price is $344 total per night
$344 total
Jul 30 - Jul 31
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Washer
Dryer
Spacious 4 Bedroom Home w/ Hot Tub

Spacious 4 Bedroom Home w/ Hot Tub

14.51 mi from city center
$519 nightly
The price is $556 total per night
$556 total
Jul 31 - Aug 1
Total includes taxes and fees
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
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

17.47 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

16.27 mi from city center
$276 nightly
The price is $293 total per night
$293 total
Jul 27 - Jul 28
Total includes 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
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

16.95 mi from city center
Guests staying at this cottage enjoy a sauna, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Kitchen
Washer
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

17.79 mi from city center
At this houseboat, guests have access to barbecue grills.
Kitchen
Pet friendly
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
17.85 mi from city center
At this houseboat, guests have access to barbecue grills.
Kitchen
Pet friendly
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

17.87 mi from city center
At this vacation home, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Pool
Kitchen
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

17.87 mi from city center
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
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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 Beach Large Group Rentals

How to Book Vacation Rentals in Chesapeake Beach



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

Chesapeake Beach vacation rentals range in price, starting at $293 per night.


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

Orbitz offers a wide range of Chesapeake Beach 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 Beach condo rentals.


🏠 Is it free to cancel my Chesapeake Beach 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 Beach 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 Beach. 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 Beach?

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 Beach apartments and enjoy an extended stay.


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

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 Beach package deals will get you even more savings.

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