113+ Private Villas and Holiday Rentals in Chesapeake Beach |
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Chesapeake Beach Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesapeake Beach

Discover more than 113 vacation rentals available in Chesapeake Beach. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesapeake Beach.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesapeake Beach, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesapeake Beach. On average, places to stay near Chesapeake Beach offer 1033.61 ft², with nightly prices averaging ZA R6,016.

With Casai, finding and comparing holiday rentals in Chesapeake Beach is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Chesapeake Beach

Type Count
Vacation Homes 82
Holiday Apartments 14
Cottages 14

Use these Quick Filters to Find a Holiday Rental in Chesapeake Beach

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chesapeake Beach.

Weather in Chesapeake Beach, MD

View the weather forecast for Chesapeake Beach before booking your Chesapeake Beach Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chesapeake Beach, MD

Casai offers a large selection of top attractions around Chesapeake Beach . Research things to do on your vacation before you visit Chesapeake Beach.


Chesapeake Beach Water Park
Rod n Reel Charter Fishing
Breezy Point Beach
Bruce Gabrielson's Surf Art Gallery and Museum
Chesapeake Beach Railway Museum
Six Flags America
Show Place Arena
Calvert Cliffs State Park
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Allen Pond Park
Chesapeake Bay Maritime Museum
Oxford Museum
Maryland Quiet Waters Park
St John's College
St. Charles Towne Center
Renditions Golf Club
Cove Point Lighthouse
Running Hare Vineyard

Other Places to Stay in Chesapeake Beach, MD


Bruce Gabrielson's Surf Art Gallery and Museum 95 Properties
Chesapeake Beach Water Park 82 Properties
Chesapeake Beach Railway Museum 82 Properties
Rod n Reel Charter Fishing 82 Properties
Breezy Point Beach 49 Properties

Frequently Asked Questions About Chesapeake Beach?

What are the top holiday rentals in Chesapeake Beach?

With numerous options available in Chesapeake Beach, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesapeake Beach:

Which holiday homes in Chesapeake Beach are best for families?

If you're searching for a family-friendly holiday home in Chesapeake Beach, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesapeake Beach:

How many Casai.co.za holiday rentals are available in Chesapeake Beach?

As of 2025, Casai boasts over 113 properties listed in the Chesapeake Beach area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesapeake Beach.


People Also Ask

There are 113 Chesapeake Beach, MD Holiday Rentals

Recently Booked Holiday Rentals in Chesapeake Beach