Photo by Ronanne Vinson

Chesapeake Beach holiday homes

We found 783 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 10 homes and other holiday rentals in Chesapeake Beach that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, which might include parking and a fireplace. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the beachside setting in Chesapeake Beach

Enjoy the live music and other features of Chesapeake Beach. This relaxing and romantic city is well known for its restaurants, spas and beaches. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chesapeake Beach

Are you hoping to find attractions to see during your stay? Venture out of your holiday home and experience everything that makes Chesapeake Beach a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Beach Water Park (0.2 mi / 0.3 km)
  • Renditions Golf Club (16.5 mi / 26.6 km)
  • Phillips Wharf Environmental Center (11.1 mi / 17.8 km)
  • Running Hare Vineyard (13.6 mi / 21.9 km)
  • Lake Presidential Golf Club (14.9 mi / 24 km)
  • South River Golf Links (15.7 mi / 25.2 km)

Exploring the natural features in Chesapeake Beach

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chesapeake Beach is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (5.2 mi / 8.3 km)
  • Jefferson Patterson Park and Museum (20.3 mi / 32.7 km)
  • Calvert Cliffs State Park (21.3 mi / 34.3 km)
  • Blackwater National Wildlife Refuge (29.2 mi / 47 km)
  • Shadyside Park (10.6 mi / 17 km)
  • Smithsonian Environmental Research Center (13.4 mi / 21.6 km)

Seasonal weather averages in Chesapeake Beach

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 24°C.

How to get to and around Chesapeake Beach

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.5 mi (42.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chesapeake Beach?

Based on our research, houses are the most sought-after holiday property type in Chesapeake Beach. But as you might expect, everyone's idea of an awesome stay is bound to be different. Bookabach has holiday homes with every shape, size and budget in mind, so you're sure to discover your ideal match.

How much does it cost to rent a holiday home in Chesapeake Beach?

Several things influence how much you pay for a holiday home in Chesapeake Beach, like the length of stay, season and type of property. But, all of our holiday homes have something in common — excellent value. Just add your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Chesapeake Beach?

The average price for a holiday home near the beach in Chesapeake Beach depends on when you're going and the style and size of property you're searching for. You can easily find prices on Bookabach by entering your preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday homes in Chesapeake Beach?

Yes. There are. You can choose from seven holiday homes that allow pets in Chesapeake Beach. Plenty of our pet-friendly holiday homes even have a garden for your four-legged fur baby to run around in, dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect pad on Bookabach.

What are popular home amenities in Chesapeake Beach?

When it comes to home amenities that guests are looking for in Chesapeake Beach, a nearby waterfront, nearby museums and a water view are at the top of the list. With Bookabach holiday homes, there are options to match your style and taste, whether you're going on a holiday with family, friends or even pets.

Are there large group holiday homes in Chesapeake Beach?

With six Chesapeake Beach holiday homes that can accommodate five or more people, you can invite a few extra pals or family members along. Whether you're planning an informal get-together or a special event, we'll help you find a comfy space to match the occasion.

Are there holiday homes in Chesapeake Beach that welcome kids?

With seven family-friendly holiday properties to pick from in Chesapeake Beach, now is a fantastic time to introduce your children to the thrills of travel. Click on our "Properties good for families" filter to discover stays loaded with amenities ideal for travelling families, like dining rooms, pools, bunk beds and hot tubs.

What are the top attractions for families in Chesapeake Beach?

Keeping the kids occupied during your stay in Chesapeake Beach is a snap with these leading family-friendly attractions:

  • Breezy Point Beach
  • Chesapeake Beach Water Park
  • Bayside History Museum

Can I find two-bedroom holiday homes in Chesapeake Beach?

Gather your family and relax in total privacy and comfort in one of the four two-bedroom holiday homes Chesapeake Beach has to offer.

Are there holiday homes with WiFi in Chesapeake Beach?

Chesapeake Beach has two holiday homes with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Bookabach homes make it easy to get online.

How can I find holiday homes with air conditioning in Chesapeake Beach?

Chesapeake Beach has seven holiday homes where you can relax in air-conditioned comfort. To book a stay on Bookabach that has this amenity, enter your dates of travel and use the convenient filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Chesapeake Beach?

The minimum required age is normally 16, 18 or 21. It can vary between properties on Bookabach, so check the rules of your preferred Chesapeake Beach holiday home before making a booking.

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