Holiday Rentals in Chesapeake Beach
Save an average of 15% on thousands of properties with Expedia Rewards
Most properties are fully refundable. Because flexibility matters.
Search over 2.9 imllion properties and 550 airlines worldwide
Check Chesapeake Beach holiday rental availability
Holiday Rentals in Chesapeake Beach
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Mid-Century Modern and Marvelous on the Bay
The Blue Crab Beach House - Free beach passes
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Charming Cottage with Hot Tub 1 Block from the Bay
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Maryland Vacation Rental w/ Private Pool & Dock
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
7 mins away from Downtown Annapolis
The Lazy Crab Beach House - Free beach passes
Charming Annapolis WaterVIEW Home
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relaxing Waterfront Cottage Near St Michaels, Maryland
Updated North Beach Cottage: Pet Friendly!
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Pool and Bay Views on wrap around deck in Kent Island
Other types of properties in Chesapeake Beach you may be interested in
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Mid-Century Modern and Marvelous on the Bay
SpringHill Suites by Marriott Annapolis
Everything you need to know about Chesapeake Beach holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chesapeake Beach holiday rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chesapeake Beach. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chesapeake Beach holiday rentals we have selected for you start as low as €239 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Chesapeake Beach rentals
At Expedia, we put the best Chesapeake Beach holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chesapeake Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake Beach holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.