Chesapeake Beach, Maryland Vacation Rentals

Explore 91 rental homes and villas in Chesapeake Beach, Maryland for your next vacation or business travel. With private vacation home rentals, enjoy a more personalized stay and a wide range of amenities such as Air Condition Homes, Pet-Friendly Homes and Best Affordable Homes. With a wide range of homes to offer, pricing can start as low as $85 per night with homes containing as many as 8 bedrooms and 7 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

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Chesapeake Beach Overview
Nestled along the tranquil shores of the Chesapeake Bay, Chesapeake Beach, Maryland, beckons as an idyllic retreat, where the gentle lapping of waves and the promise of leisurely days await. This coastal gem is not only a feast for the eyes with its stunning waterfront vistas but also a haven for those seeking the comforts of a private home-away-from-home experience. Imagine waking up to the soft glow of sunrise over the bay from the privacy of your own rented home, complete with all the amenities you could desire. Many of these homes boast not only pet-friendly accommodations, ensuring your furry friends can join in on the fun, but also feature inviting swimming pools, offering a refreshing respite from the summer heat. The heart of Chesapeake Beach's allure is undoubtedly its pristine beach and boardwalk, where the simple pleasures of sunbathing, swimming, and strolling can be savored. The waterfront is a tapestry of activity, with the Chesapeake Beach Water Park serving as a family favorite. Here, laughter fills the air as visitors of all ages delight in the water slides, relax on the lazy river, and splash in the kids' activity pool. Anglers will find themselves in paradise, with Chesapeake Beach renowned for its rich fishing culture. Charter a boat for an unforgettable day on the bay, reeling in striped bass and bluefish, and return to the comfort of your private rental to grill the day's catch. The Rod 'N' Reel Resort marina stands as a testament to the town's nautical heritage, offering more than just fishing charters but also panoramic views that are nothing short of breathtaking. History comes alive at the Chesapeake Beach Railway Museum, where the echoes of the past resonate within the walls of the original train station. Delve into the town's storied history and the pivotal role the railway played in its development. For a change of pace, the nearby North Beach extends the invitation to explore further, with its quieter beach area perfect for those moments of reflection or a dip in the bay's welcoming waters. The town's vibrant spirit is showcased through annual events like the Stars and Stripes Festival, where the Fourth of July is celebrated with fireworks and fanfare. Chesapeake Beach is a tapestry of experiences, from the serenity of its shores to the adventure that lies beneath its waves. It's a place where history whispers through the ocean breeze and where every rented home promises a personal oasis. Whether seeking solace in the lap of luxury or adventure on the open water, Chesapeake Beach is a coastal sanctuary that offers an unforgettable escape.
Cultural Attractions in Chesapeake Beach
Chesapeake Beach, Maryland, may not be the first destination that comes to mind for a cultural enthusiast, but this charming coastal town offers a unique blend of history, arts, and local customs that can provide a delightful experience for those looking to immerse themselves in culture. Begin your cultural exploration at the Chesapeake Beach Railway Museum, where you can delve into the town's history as a turn-of-the-century seaside resort. The museum, housed in the original railway station, offers a glimpse into the past with its collection of photographs, artifacts, and memorabilia that tell the story of the resort's heyday and the railway that made it all possible. Art lovers will appreciate the local art scene that can be found in the town's small galleries and craft shops. While Chesapeake Beach may not have large art museums, the intimate settings allow for a personal connection with the art and the artists, many of whom draw inspiration from the town's picturesque surroundings and maritime heritage. Live music can be enjoyed at several venues and seasonal events in Chesapeake Beach. The town's bandstand and waterfront park often host concerts, especially during the summer months, featuring a variety of genres from local and regional musicians. The sounds of jazz, blues, and acoustic performances blend with the gentle lapping of the bay's waves, creating a serene musical experience. For a deeper dive into local customs, the Chesapeake Beach Water Park is not only a place for fun and relaxation but also a venue where community events take place. Here, you can mingle with locals and experience the town's friendly atmosphere. Additionally, the town's proximity to the water means that seafood plays a significant role in local cuisine. Dining at one of the waterfront restaurants offers not only fresh, delicious dishes but also an insight into the town's fishing and oystering traditions. While Chesapeake Beach may offer a quieter cultural scene compared to larger cities, its charm lies in the authentic and intimate experiences it provides. The town's relaxed pace allows visitors to savor each cultural encounter, whether it's through the historical narratives, the local artistry, or the simple pleasure of a live music performance by the bay.
Kids IconFamily friendly activities in Chesapeake Beach
Chesapeake Beach, Maryland, is a delightful coastal town that offers a treasure trove of activities for families traveling with children. The town's laid-back atmosphere and scenic beauty make it an ideal spot for a family getaway. Start your adventure at the Chesapeake Beach Water Park, where kids can splash around in a variety of water slides and pools. The park features a lazy river, a lagoon, and fountains that are perfect for younger children, while thrill-seekers can enjoy the excitement of the water slides. The park also offers a special toddler pool for the littlest ones to enjoy safely. For a taste of history and education, take the family to the Chesapeake Beach Railway Museum. Here, children can learn about the rich history of the town and the railway that once brought vacationers to its shores. The museum is housed in the original train station and features fascinating exhibits, including a model train display that is sure to captivate young minds. Nature-loving families will enjoy a visit to the Chesapeake Beach Railway Trail. This boardwalk trail meanders through marshes and wooded areas, offering opportunities to spot local wildlife and enjoy the natural beauty of the region. It's an easy walk for children and provides a peaceful setting for a family stroll. Fishing enthusiasts can take advantage of the town's location on the Chesapeake Bay by heading to the Rod 'n' Reel Resort's fishing pier. It's a great place for kids to try their hand at catching fish, and the excitement of reeling in a big one is an experience they won't soon forget. For a unique experience, consider a family cruise on the Miss Chesapeake Beach, where you can explore the bay, learn about the local ecosystem, and maybe even spot some dolphins. These cruises are both educational and entertaining, making them a hit with kids and adults alike. When it's time to eat, Chesapeake Beach offers a variety of family-friendly dining options, many of which serve up delicious seafood fresh from the bay. Enjoy a meal with a view at one of the waterfront restaurants, where children can watch boats come and go as they dine. Chesapeake Beach is a gem that combines relaxation, fun, and learning in a beautiful coastal setting. It's a place where families can create lasting memories while enjoying the simple pleasures of sun, water, and togetherness.
Nature IconOutdoor activities in Chesapeake Beach
Chesapeake Beach, Maryland, is a serene coastal town that offers a delightful escape for outdoor enthusiasts and nature lovers. With its picturesque views of the Chesapeake Bay and a variety of natural attractions, it's a perfect destination for those looking to connect with the great outdoors. One of the town's most popular natural attractions is the Chesapeake Beach Railway Trail. This boardwalk trail meanders through a wetland marsh and offers a peaceful setting for walking, jogging, and bird-watching. The trail provides an excellent opportunity to observe local wildlife, including herons, ospreys, and even bald eagles. For those interested in fishing, Chesapeake Beach is a prime spot. The town's public fishing pier extends into the bay, allowing anglers to cast their lines for rockfish, bluefish, and other local species. Charter boats are also available for those looking to venture further into the bay for a day of deep-sea fishing. Water enthusiasts will enjoy the town's proximity to the bay for kayaking and paddleboarding. The calm waters of the Chesapeake Bay make for an ideal setting to paddle and explore the coastline, with the chance to spot marine life and enjoy the scenic beauty of the area. Nature lovers should not miss the opportunity to visit the nearby North Beach, where the North Beach Boardwalk offers stunning views of the bay and a chance to relax on the sandy beach. The adjacent Wetlands Overlook Park provides a platform for observing the local ecosystem and is a tranquil spot for nature photography. For a more immersive experience, take a short drive to the Calvert Cliffs State Park, known for its impressive cliffs and fossil hunting opportunities. The park's sandy beach is a hidden gem where visitors can search for ancient shark teeth and other prehistoric fossils. Hiking trails through the park's diverse landscapes offer the chance to see a variety of plant and animal life. Lastly, the Breezy Point Beach and Campground is another local favorite, offering a sandy beach, a fishing pier, and picnic areas. It's a great spot for a family day out, complete with swimming and beachcombing. Chesapeake Beach is a delightful blend of maritime charm and natural beauty, providing a wealth of outdoor activities that cater to the desires of nature enthusiasts. Whether you're looking to relax by the water, explore local wildlife, or enjoy active pursuits like fishing and hiking, Chesapeake Beach is a destination that truly celebrates the great outdoors.
Weather IconWeather in Chesapeake Beach
Chesapeake Beach, Maryland, offers a classic Mid-Atlantic climate with four distinct seasons, each bringing its own unique weather patterns and opportunities for visitors to enjoy the area's natural beauty and attractions. Summer in Chesapeake Beach, from June to August, is warm and often humid, with average high temperatures in the mid-80s Fahrenheit (around 30°C). This is the peak season for beachgoers and water activities, as the Chesapeake Bay provides a refreshing escape from the heat. Occasional thunderstorms can occur, bringing brief but heavy downpours. Autumn, from September to November, sees a gradual decrease in temperature and humidity. The highs range from the low 70s to the mid-50s Fahrenheit (around 22°C to 13°C). This season is popular for its comfortable weather and the stunning fall foliage that decorates the surrounding landscapes. Precipitation is moderate, and outdoor activities are particularly enjoyable during this time. Winter, from December to February, can be quite cold with temperatures often ranging from the low 30s to the mid-40s Fahrenheit (0°C to 7°C). Snowfall is possible, though not as heavy as in more northern regions, making Chesapeake Beach a quieter destination during these months. The serene winter landscape offers a different kind of beauty, with opportunities for peaceful walks along the shore. Spring, from March to May, brings a gradual warming with temperatures ranging from the upper 40s to the high 60s Fahrenheit (around 9°C to 20°C). The area comes to life with blooming flowers and budding trees, making it a delightful time for nature walks and outdoor exploration. Rainfall is fairly common in the spring, so it's wise to have an umbrella handy. The most popular weather conditions are prevalent during the late spring to early fall, when visitors can take full advantage of the outdoor activities and the beach. The climate is especially pleasant in late spring and early autumn, with mild temperatures and lower humidity levels, offering an ideal time for those looking to avoid the summer crowds while still enjoying comfortable weather. Whether you're planning to relax on the beach, explore the local seafood scene, or engage in water sports on the bay, Chesapeake Beach has a season for every traveler's preference. Keep in mind that weather can be unpredictable, so it's always a good idea to check the forecast and pack accordingly for your visit.
Transportation in Chesapeake Beach
Chesapeake Beach, Maryland, is a charming waterfront town that offers a serene escape with its beautiful bay views, quaint neighborhoods, and relaxing atmosphere. While it may not have the extensive transportation networks of a major city, there are still several ways for travelers to arrive, depart, and explore this delightful destination. Most visitors arrive by car, as Chesapeake Beach is conveniently located about an hour's drive from Washington, D.C., and is easily accessible via Maryland Route 260. This makes it an ideal spot for a road trip or a weekend getaway. There is no direct train service to Chesapeake Beach, but the nearby town of Upper Marlboro is serviced by the MARC Train, which connects to Washington, D.C., and other parts of Maryland. From there, a taxi or ride-sharing service can complete the journey to Chesapeake Beach. For those flying in, the closest major airport is Ronald Reagan Washington National Airport (DCA), located in Arlington, Virginia. From the airport, renting a car or using a ride-sharing service would be the most convenient options to reach Chesapeake Beach. Baltimore/Washington International Thurgood Marshall Airport (BWI) is another option, though it is a bit further away. Once in Chesapeake Beach, getting around is relatively straightforward. The town itself is small and can be quite walkable, especially in the areas near the waterfront and the central attractions like the Chesapeake Beach Railway Museum and the Chesapeake Beach Water Park. However, if you plan to explore the surrounding areas or visit nearby attractions such as the North Beach or the Calvert Cliffs State Park, having a car would be beneficial. For those who prefer not to drive, local taxi services and ride-sharing options are available, though they may be less abundant than in larger cities. Biking is also a pleasant way to get around, particularly during the warmer months, and it allows visitors to enjoy the scenic views at a leisurely pace. In summary, while Chesapeake Beach may not have the public transportation infrastructure of a metropolitan area, it remains accessible and navigable for visitors. The town's compact size and scenic charm make it a delightful place to explore on foot or by bike, but having a car will provide the greatest flexibility for those looking to discover all that the area has to offer.