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Chesapeake Beach holiday lettings

We found 848 holiday rentals — enter your dates for availability

Discover a selection of 7 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:16 Jan - 23 Jan

Image gallery for Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

A great spot to soak in the views of the Chesapeake Bay.
10 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

North Beach, MD

15% off
Price is £3,188
for 7 nights, 1 home
£455 per night
includes taxes & fees
Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

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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.

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.

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

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.

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)
  • Fridays Creek Winery (7.6 mi / 12.2 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)

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 best area to stay in Chesapeake Beach when booking a holiday rental?
When considering a holiday rental in Chesapeake Beach, Maryland, a popular area to stay is along the waterfront, particularly close to the Chesapeake Beach Railway Museum. This charming neighbourhood offers a delightful blend of scenic views and easy access to local attractions. With approximately 30 rental properties available in this area, visitors can choose from a range of options, from quaint cottages to more spacious homes.

Staying near the beach allows you to enjoy the beautiful sandy shores and the calming sounds of the waves, great for a relaxing getaway. The nearby Chesapeake Beach Water Park is a fantastic attraction for families, featuring fun water slides and pools, making it an ideal spot for children and adults alike. Additionally, the local dining scene is vibrant, with several restaurants offering fresh seafood and stunning views of the bay.

Another appealing area for holiday rentals is the North Beach neighbourhood. This area is known for its picturesque boardwalk and quaint shops, providing a lovely atmosphere for leisurely strolls. With a similar number of rental properties available, North Beach offers a charming coastal experience, complete with access to beaches and parks. The proximity to the North Beach Park, with its picnic areas and playgrounds, makes it an excellent choice for families looking to enjoy the outdoors.
How much does it cost to rent a holiday home in Chesapeake Beach?
Prices for holiday rentals in Chesapeake Beach vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesapeake Beach to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chesapeake Beach holiday house rentals?
You can find great discounts on house rentals in Chesapeake Beach on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chesapeake Beach?
For renting a beach house in Chesapeake Beach, the area along the Chesapeake Bay is particularly appealing. The beachfront near the Chesapeake Beach Resort offers a selection of holiday rentals with picturesque views of the water. Many of these properties feature amenities such as private balconies, outdoor seating areas, and fully equipped kitchens, making them superb for families or groups seeking a relaxing getaway by the sea.

Additionally, the nearby Breezy Point area is known for its charming beach houses that often come with direct beach access, outdoor showers, and spacious decks ideal for barbecues. This area provides a laid-back atmosphere, with opportunities for fishing, crabbing, and enjoying long walks along the sandy shores.
What is the most popular type of holiday rental accomodation in Chesapeake Beach?
In Chesapeake Beach, holiday houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties are typically situated in charming neighbourhoods close to the waterfront and local attractions such as the Chesapeake Beach Resort and Spa and the Boardwalk. Most holiday houses come equipped with multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor decks or patios, ideal for enjoying the pleasant coastal climate. Cottages also provide a cosy atmosphere, often featuring quaint decor and easy access to the beach, making them superb for couples or small families.
Are there any family house rentals in Chesapeake Beach?
In Chesapeake Beach, Maryland, there are about ten family-friendly house rentals available, making it an excellent choice for those travelling with children. The area is known for its charming waterfront and proximity to various recreational activities. Many of these homes offer spacious living areas, well-equipped kitchens, and outdoor spaces where families can enjoy barbecues or play games together.

Visitors can take advantage of nearby attractions such as the Chesapeake Beach Water Park, which features pools and slides, superb for a fun day out with the kids. Additionally, the local beaches provide opportunities for swimming, sunbathing, and beachcombing. Families will also appreciate the convenience of having amenities like Wi-Fi and laundry facilities to make their stay more comfortable.
Can I rent a holiday home with a pool or hot tub in Chesapeake Beach?
In Chesapeake Beach, there are several holiday homes available for rent that feature pools and hot tubs. This charming coastal town offers a delightful mix of relaxation and outdoor activities, making it an appealing destination for travellers. Many of the properties come equipped with private pools, inviting hot tubs, and outdoor entertaining areas, great for enjoying the pleasant Maryland weather.
Can I find long-stay holiday rentals in Chesapeake Beach?
A long-stay holiday rental in Chesapeake Beach is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chesapeake Beach?
In Chesapeake Beach, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry companions along. Many of these properties offer amenities such as spacious backyards, outdoor seating areas, and fully equipped kitchens, suiting families and groups seeking a comfortable stay.

The area is known for its beautiful waterfront, and many holiday homes are just a short walk from the beach, allowing for easy access to sandy shores where pets can enjoy the outdoors. Additionally, the nearby Chesapeake Beach Railway Trail is superb for leisurely walks with pets, offering scenic views and a pleasant atmosphere.
Are there any remote work holiday rentals in Chesapeake Beach?
In Chesapeake Beach, Maryland, there are several remote work holiday rentals available, making it a suitable spot for those looking to blend work with leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desks, and comfortable office chairs, allowing you to set up a productive workspace. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesapeake Beach holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chesapeake Beach with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chesapeake Beach?
In Chesapeake Beach, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature patios, providing a lovely outdoor space for relaxation or dining al fresco. Additionally, rentals typically come with cookware, dishware, and utensils, making it convenient for travellers to enjoy home-cooked meals. Microwaves are commonly available as well, adding to the comfort and functionality of these holiday rentals.
When is the best time to visit Chesapeake Beach for a holiday rental?
The best time to visit Chesapeake Beach for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and beachgoers eager to soak up the sun along the beautiful shores of the Chesapeake Bay. Visitors can relish in various outdoor activities, from swimming and sunbathing to fishing and kayaking, all while enjoying the warm, pleasant climate, typically ranging from the mid-20s to low 30s Celsius.

During these summer months, the atmosphere is lively, with plenty of events and activities to engage in, including local festivals and waterfront dining experiences that enhance your stay. The beaches are bustling, making it a superb time for socialising and creating memories with loved ones.

If you're looking for a more budget-friendly option, consider planning your visit in December. During this time, this month offers a unique charm with holiday decorations and seasonal events, providing a different perspective on Chesapeake Beach.
How early should I book a Chesapeake Beach holiday rental?
Book your Chesapeake Beach holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesapeake Beach?
In Chesapeake Beach, visitors can enjoy a variety of attractions that highlight the charm of this coastal town. The Chesapeake Beach Railway Trail offers scenic views and a lovely path for walking or cycling, making it a great spot for outdoor enthusiasts. Close by, the Chesapeake Beach Water Park provides family-friendly fun with water slides and pools, superb for a day of relaxation and entertainment by the sea.

For those interested in marine life, the nearby Calvert Marine Museum is a fantastic destination, showcasing local maritime history and offering engaging exhibits for all ages. The beach itself is a highlight, where visitors can stroll along the shoreline, enjoy fishing, or simply soak in the sun.
Can I change or cancel my Chesapeake Beach home rental booking on Vrbo?
To find Chesapeake Beach holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chesapeake Beach holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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