Compare Chesapeake Beach Vacation Rentals

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Chesapeake Beach Rentals

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.
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

13.29 mi from city center
$296 nightly
The price is $317 total per night
$317 total
Oct 1 - Oct 2
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

14.11 mi from city center
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

17.61 mi from city center
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
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.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

20.39 mi from city center
At this vacation home, guests have access to an outdoor pool, a sauna, and a hot tub. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
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
Walk to Everything House

Walk to Everything House

17.75 mi from city center
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
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.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

17.9 mi from city center
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Riverfront Retreat 7mil from MD Renaissance Fest!

Riverfront Retreat 7mil from MD Renaissance Fest!

18.45 mi from city center
At this vacation home, guests have access to a gym, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
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 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 $317 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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