24917+ Private Villas and Holiday Rentals in Chesapeake Bay |
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  2. Chesapeake Bay

Chesapeake Bay Holiday Rentals

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

Discover more than 24917 vacation rentals available in Chesapeake Bay. 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 Bay.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesapeake Bay, 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 Bay. On average, places to stay near Chesapeake Bay offer 744.54 ft², with nightly prices averaging US $333.

With Casai, finding and comparing holiday rentals in Chesapeake Bay 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 Bay

Type Count
Vacation Homes 10594
Holiday Apartments 6943
Cottages 572
Villas 254

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

★ 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 Bay.

Weather in Chesapeake Bay, US

View the weather forecast for Chesapeake Bay before booking your Chesapeake Bay 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 Bay, US

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


White House
Busch Gardens Williamsburg
National Mall
Virginia Beach Boardwalk
Washington Monument
National Aquarium in Baltimore
Colonial Williamsburg
Walter E. Washington Convention Center
George Washington University
Arlington National Cemetery
Smithsonian National Air and Space Museum
Naval Station Norfolk
Lincoln Memorial
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Capital One Arena
United States Capitol
Baltimore Convention Center
National Museum of Natural History

Other Places to Stay in Chesapeake Bay, US


Maryland 17,361 Properties
Northern Chesapeake Bay 10,367 Properties
Washington 3,406 Properties
Norfolk - Virginia Beach 3,335 Properties
District of Columbia 3,219 Properties
Virginia Beach 2,188 Properties
Northwest 1,957 Properties
Baltimore 1,590 Properties
Anne Arundel County 1,524 Properties
James City County 1,384 Properties
Williamsburg 1,381 Properties
Northeast Virginia Beach 1,314 Properties

Frequently Asked Questions About Chesapeake Bay?

What are the top holiday rentals in Chesapeake Bay?

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

How many holiday rentals have private pools in Chesapeake Bay?

Discover a selection of holiday rentals with private pools near Chesapeake Bay with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chesapeake Bay are best for families?

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

How many Casai.nz holiday rentals are available in Chesapeake Bay?

As of 2025, Casai boasts over 24917 properties listed in the Chesapeake Bay area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesapeake Bay.

Nearby Neighborhood (16) 
Neighborhood Property Count
Northwest Vacation Rentals in Chesapeake Bay, US 1957
Northeast Virginia Beach Vacation Rentals in Chesapeake Bay, US 1314
Northeast Vacation Rentals in Chesapeake Bay, US 744
Downtown Washington D.C. Vacation Rentals in Chesapeake Bay, US 631
Capitol Hill Vacation Rentals in Chesapeake Bay, US 616
Downtown Baltimore Vacation Rentals in Chesapeake Bay, US 595
Crystal City Vacation Rentals in Chesapeake Bay, US 256
Rosslyn Vacation Rentals in Chesapeake Bay, US 219
Dupont Circle Vacation Rentals in Chesapeake Bay, US 160
Downtown Vacation Rentals in Chesapeake Bay, US 151
Old Town Alexandria Vacation Rentals in Chesapeake Bay, US 114
Fells Point Vacation Rentals in Chesapeake Bay, US 71
Georgetown Vacation Rentals in Chesapeake Bay, US 64
Foggy Bottom Vacation Rentals in Chesapeake Bay, US 62
Inner Harbor Vacation Rentals in Chesapeake Bay, US 43
Pentagon City Vacation Rentals in Chesapeake Bay, US 42

People Also Ask

There are 24917 Chesapeake Bay, US Holiday Rentals

Recently Booked Holiday Rentals in Chesapeake Bay