Photo by Ronanne Vinson

Chesapeake Beach holiday lettings

We found 831 holiday rentals — enter your dates for availability

Discover a selection of 9 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.

Holiday rentals with weekly discounts - Chesapeake Beach

Showing deals for:10 Oct - 17 Oct
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Why visit Chesapeake Beach

  • Stunning beaches: Enjoy the picturesque Breezy Point Beach, perfect for sunbathing and relaxation.
  • Family-friendly attractions: Dive into fun at the popular Chesapeake Beach Water Park, ideal for all ages.
  • Charming parks: Explore scenic parks that offer a tranquil escape and opportunities for outdoor activities.
  • Eclectic accommodation: Choose from a variety of delightful holiday rentals, including cottages and modern apartments.
  • Welcoming community: Experience the friendly atmosphere and create lasting memories in this charming coastal town.

Popular types of accommodation in Chesapeake Beach

Vrbo offers a delightful selection of vacation rentals in Chesapeake Beach, catering to various preferences. Whether you're seeking a private holiday home, a charming cottage, or a modern apartment, you'll find the perfect accommodation for your getaway. The choice ultimately depends on your travel companions and planned activities. Discover the ideal house rental for your next escape and enjoy the beauty of Chesapeake Beach.

  • Houses: The top choice for holiday rentals in Chesapeake Beach, offering spacious and comfortable stays perfect for families or groups.
  • Cottages: A charming option, these quaint retreats provide a cosy atmosphere for a delightful seaside experience.
  • Apartments: Ideal for those seeking convenience, these self-contained units are perfect for couples or solo travellers.
  • Condos: Offering modern amenities and often stunning views, condos are a popular selection for vacationers.
  • Cabins: For a rustic getaway, cabins provide a unique and tranquil experience amid nature.**

Top attractions in Chesapeake Beach

Chesapeake Beach offers a delightful blend of outdoor activities, perfect for families and couples alike. Visitors can enjoy the scenic parks, sandy beaches, and the popular Chesapeake Beach Water Park. With a focus on eco-friendly experiences, this charming destination is ideal for those seeking relaxation and adventure in a picturesque setting.

  • Breezy Point Beach: This lovely beach offers a relaxing atmosphere with golden sands and gentle waves, perfect for sunbathing and leisurely strolls along the shore, immersing yourself in the idyllic beach vibes.
  • Rod n Reel Charter Fishing: Experience the thrill of fishing in the beautiful waters of Chesapeake Beach. This marina provides adventure and outdoor fun, with opportunities for deep-sea fishing, making it a must-visit for enthusiasts.
  • Chesapeake Beach Railway Museum: Delve into the rich history of the region at this charming museum. It showcases the cultural heritage of the Chesapeake Beach Railway, offering fascinating insights into local history.

Things to do recommended for couples

For a romantic getaway in Chesapeake Beach, visit Fridays Creek Winery for a delightful wine experience, or indulge in luxury at Old South Country Club. For a bit of fun, try R&J's PlayPark for some mini-golf adventure. Perfect for couples seeking memorable moments together!

Things to do recommended for families

Your family will have a splendid time at Chesapeake Beach, enjoying the thrills of the Chesapeake Beach Water Park. For sports enthusiasts, Prince George's Stadium is just a short drive away, while Allen Pond Park offers a relaxing retreat for wellness and leisure. Perfect for all ages!

Things to do recommended for groups

Groups visiting Chesapeake Beach can enjoy a round of golf at Lake Presidential Golf Club, explore the shops at Annapolis Harbour Center, or visit the Wild Bird Center for a unique experience. Each venue offers a vibrant atmosphere perfect for group activities and bonding.

Booking with Vrbo is simple

Are you hoping to make your next trip more affordable? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, by opting for a longer stay, you could enjoy considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Chesapeake Beach

Chesapeake Beach, Maryland, offers a delightful blend of relaxation and recreation, making it ideal for families and couples alike. Explore the charming shoreline, bask in the sun at Breezy Point Beach, or enjoy the friendly atmosphere of nearby Virginia Beach. With its scenic views and welcoming community, Chesapeake Beach promises a memorable getaway where you can unwind and create lasting memories with loved ones.

  • North Beach: North Beach is a charming seaside city located a mere 559m from Chesapeake Beach. This vibrant locale is perfect for those seeking outdoor adventures and scenic beauty. Visitors can enjoy a delightful stroll along the boardwalk, indulge in shopping at local boutiques, or simply relax in the recreational areas. The nearby beach and family-friendly beach provide a perfect setting for sunbathing and swimming. Additionally, the proximity to the national state park offers opportunities for hiking and wildlife spotting, making North Beach an excellent destination for families and nature lovers alike.
  • Rose Haven: Situated 1.2km from Chesapeake Beach, Rose Haven is a picturesque village that beckons travellers with its outdoor charm and romantic atmosphere. The village is known for its delightful water park and recreational areas, offering fun for all ages. Visitors can explore the scenic boardwalk while enjoying views of the nearby lake and beach. Notable landmarks include a local monument that adds a touch of history to the area. Rose Haven is ideal for couples and families looking to create lasting memories in a serene and beautiful setting.
  • Owings: Owings, located 2.5km from Chesapeake Beach, is a vibrant city that promises adventure and outdoor experiences. With its recreational areas and amusement park, Owings is perfect for thrill-seekers and families alike. The city’s close proximity to stunning natural landmarks such as beaches, lakes, and a national state park means there are plenty of opportunities for hiking, fishing, and exploring the great outdoors. Whether you’re looking for a day of fun or a scenic escape, Owings offers a delightful mix of activities and attractions.

Best time to go to Chesapeake Beach

If you're planning a trip to Chesapeake Beach, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.0°F (2.2°C)Light RainMostly SunnyLowSlightly Low
February38.3°F (3.5°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageSlightly Low
April55.2°F (12.9°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyHighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnyHighSlightly High
August76.5°F (24.7°C)Light RainMostly SunnyHighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.9°F (9.4°C)Light RainMostly SunnyLowAverage
December41.7°F (5.4°C)Light RainMostly SunnyLowAverage

What do I need to keep in mind when booking a vacation in 'Chesapeake Beach

If you’re travelling with a group, family, pets, or planning an extended stay, it’s essential to refine your search based on your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chesapeake Beach with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options, and many more, on Vrbo.
  • Traveling to Chesapeake Beach with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it would be wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Chesapeake Beach: For many, a family holiday isn't truly complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Chesapeake Beach: If you’re in search of holiday rentals with special offers for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last left off, or manage and organise your travel arrangements. You can easily find properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore the features of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • 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)
  • Renditions Golf Club (16.5 mi / 26.6 km)
  • Marlton Golf Course (14.6 mi / 23.4 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)
  • Merkle Wildlife Sanctuary (9.6 mi / 15.5 km)
  • Shadyside Park (10.6 mi / 17 km)
  • Triton Beach (13.3 mi / 21.3 km)
  • Smithsonian Environmental Research Center (13.4 mi / 21.6 km)
  • Battle Creek Cypress Swamp Sanctuary (14.4 mi / 23.1 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 rental 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. Vrbo 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 rental in Chesapeake Beach?
Several things influence how much you pay for a holiday rental 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 rental 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 Vrbo 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 rentals in Chesapeake Beach?
Yes. There are. You can choose from seven holiday rentals that allow pets in Chesapeake Beach. Plenty of our pet-friendly holiday rentals 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 Vrbo.
What are popular rental amenities in Chesapeake Beach?
When it comes to rental 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 Vrbo 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 rentals 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 rentals 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 rentals in Chesapeake Beach?
Gather your family and relax in total privacy and comfort in one of the four two-bedroom holiday rentals Chesapeake Beach has to offer.
Are there holiday rentals with WiFi in Chesapeake Beach?
Chesapeake Beach has two holiday rentals 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 Vrbo homes make it easy to get online.
How can I find holiday rentals with air conditioning in Chesapeake Beach?
Chesapeake Beach has seven holiday rentals where you can relax in air-conditioned comfort. To book a stay on Vrbo 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 rental in Chesapeake Beach?
The minimum required age is normally 16, 18 or 21. It can vary between properties on Vrbo, so check the rules of your preferred Chesapeake Beach holiday rental before making a booking.
How long can I rent a holiday rental in Chesapeake Beach for?
It all depends on the Chesapeake Beach property. To browse available options offering extended stays, just type your travel dates and number of people into Vrbo. You can look forward to having the entire property to yourself, along with home comforts such as a full kitchen, air conditioning and outdoor spaces where your little ones can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.

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