Deale, Maryland Vacation Rentals

Explore 68 rental homes and villas in Deale, 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 $111 per night with homes containing as many as 7 bedrooms and 7 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

Types of vacation rentals in Deale

Where to stay in Deale

Show all homes

Booking a vacation rental in Deale, Maryland?

Here are some things to know to support your visit:

Deale Overview
Nestled on the western shore of the Chesapeake Bay, Deale, Maryland, is a captivating waterfront haven that promises an idyllic escape from the daily grind. This tranquil community is a treasure trove for water lovers and those yearning for a peaceful retreat amidst nature's splendor. The allure of Deale is magnified by its renowned attractions, such as the pristine Herrington Harbour, which beckons with its sandy beaches and resort-like amenities. Here, eco-trails wind through lush gardens, offering a perfect backdrop for family picnics or a solitary ramble. The waterfront is the heart of Deale, where boating, fishing, and crabbing are not just pastimes but a way of life. The town's marinas are vibrant hubs where you can embark on a boating adventure or charter a fishing trip to delve into the bay's abundant waters. Imagine waking up in a private home rental, a space that's exclusively yours, where you can savor your morning coffee with a view of the bay's tranquil waters. Many of these homes are pet-friendly, ensuring that your furry companions can join in on the fun. For those seeking the ultimate indulgence, select a rental with a swimming pool, where you can enjoy a refreshing dip after a day of exploring or simply lounge by the water in complete privacy. Deale's culinary scene is a celebration of the local catch, with seafood restaurants offering dishes featuring fish, crabs, and oysters that have often been plucked from the bay on the very same day. Dining in Deale means relishing the freshest flavors while overlooking the water that provided them. For landlubbers, the town's picturesque streets, lined with charming homes and welcoming local businesses, create a storybook setting for leisurely walks, bird watching, and capturing the beauty of the area through photography. The maritime heritage of Deale is proudly displayed at the local museum, where visitors can immerse themselves in the town's history of fishing and boat-building, learning about the traditional methods that have shaped this community. Deale's strategic location also makes it an ideal base for exploring the wider region. A short drive takes you to the historic streets of Annapolis, home to the United States Naval Academy, while nearby parks and wildlife refuges offer encounters with Maryland's diverse coastal flora and fauna. The true essence of Deale lies in its unhurried pace of life. It's a place where time pauses, inviting you to relax and delight in the simple joys of waterfront living. Whether it's savoring a meal on a dockside deck, basking in the glow of a bay sunset, or feeling the evening breeze as it whispers through the sails, Deale is a serene and picturesque sanctuary that leaves a lasting impression. In summary, Deale, Maryland, is an enchanting destination that seamlessly weaves outdoor adventure, gastronomic pleasures, and the serenity of waterfront life into an unforgettable retreat. It's a place where each moment is a treasure, and every memory made is as enduring as the timeless tides of the Chesapeake Bay.
Cultural Attractions in Deale
Deale, Maryland, may not be the first place that comes to mind when you think of a cultural hotspot, but this charming waterfront community offers a unique and intimate experience of the arts, history, and local customs for those willing to delve into its serene setting. While Deale itself is a small, quiet town, its proximity to Annapolis and Washington D.C. allows for easy access to a wider array of cultural activities. However, Deale's local charm is found in its maritime heritage and the simplicity of its attractions, which provide a more personal encounter with the region's culture. Begin your cultural exploration at the Captain Avery Museum, housed in a 19th-century home on the waterfront. This museum offers a glimpse into the life of a waterman and the history of the Chesapeake Bay area. The museum hosts a variety of events throughout the year, including oyster festivals and local history talks, which allow visitors to engage with the traditions and customs of the region. Art enthusiasts can enjoy the local art scene at nearby galleries or by visiting artists' studios in the area. The Muddy Creek Artists Guild, for example, represents local artists and organizes studio tours and art shows, providing an opportunity to appreciate and purchase local artwork. For live music, Deale has a laid-back scene with several restaurants and bars hosting local bands and acoustic sets, especially during the summer months. The Happy Harbor and Skipper's Pier are two popular spots where you can enjoy live performances with the backdrop of the bay, offering a blend of good food, music, and scenic views. While Deale may not boast large museums or concert halls, its proximity to larger cities means that a short drive can bring you to world-class cultural institutions. Annapolis, with its historic colonial architecture, offers a rich array of cultural experiences, from the Maryland State House to the Annapolis Symphony Orchestra and the Annapolis Maritime Museum. In essence, Deale, Maryland, is a destination for those who appreciate the quieter side of cultural exploration. It's a place where you can immerse yourself in the local way of life, enjoy the arts at a leisurely pace, and experience the history and customs of the Chesapeake Bay region in an intimate and personal setting.
Kids IconFamily friendly activities in Deale
Deale, Maryland, is a charming waterfront community that offers a serene escape for families looking to enjoy the simpler pleasures of life by the Chesapeake Bay. With its laid-back atmosphere and scenic beauty, Deale provides a variety of activities that children will love. Begin your family adventure at the Herrington Harbour South, a marina resort that offers more than just boat slips. With its sandy beaches and swimming pools, kids can splash around and build sandcastles while parents relax by the water. The resort also has playgrounds and picnic areas, making it an ideal spot for a family day out. For those little anglers in the family, Deale is a prime spot for fishing. Charter a family-friendly fishing boat and head out onto the bay for a chance to catch some local fish. It's not only a fun activity but also an educational experience as children learn about the local marine life and the importance of the Chesapeake Bay ecosystem. Take a leisurely stroll along the Deale Boardwalk, where kids can watch the boats come and go, and maybe even spot some local wildlife. The boardwalk is a peaceful place for a family walk, especially during sunset when the sky is painted with vibrant colors. For a taste of local history, visit the Captain Avery Museum. The museum offers a glimpse into the life of a 19th-century waterman and his family, with interactive exhibits that engage children's curiosity about the past. The museum's grounds are also a lovely place for kids to explore, with gardens and a waterfront lawn. If your family enjoys hiking and nature, the nearby Jug Bay Wetlands Sanctuary is a must-visit. With over 1,500 acres of protected land, the sanctuary offers miles of trails and boardwalks through diverse habitats. Children can participate in nature programs, go bird watching, or simply enjoy the great outdoors. Lastly, indulge in some local cuisine at one of Deale's family-friendly restaurants. Many offer casual dining with kid-approved menus, and some even have outdoor seating where you can dine with views of the water. In Deale, Maryland, families can enjoy a relaxing getaway that combines the joys of the bay with engaging activities for children. It's a place where memories are made, and the pace of life slows down just enough for everyone to savor the moment.
Nature IconOutdoor activities in Deale
Deale, Maryland, a charming waterfront community nestled along the Western Shore of the Chesapeake Bay, offers a serene escape into nature's embrace. This picturesque destination is a treasure trove for outdoor enthusiasts and nature lovers alike, with its tranquil waters, lush landscapes, and abundant wildlife. One of the main attractions in Deale is its access to the Chesapeake Bay, a haven for boating, sailing, and fishing. The bay's rich waters are teeming with blue crabs, rockfish (striped bass), and oysters, making it a prime spot for anglers looking to reel in the catch of the day. Charter a fishing boat or join a guided tour to experience the best of the bay's bounty. Kayaking and paddleboarding are also popular activities in Deale, with the calm inlets and creeks providing the perfect setting for a peaceful paddle. Glide through the waterways and take in the scenic views, all while getting a gentle workout. The area's diverse ecosystems, including marshes and wetlands, are ideal for spotting herons, ospreys, and even bald eagles. For those who prefer to stay on land, Deale offers a variety of walking and hiking trails that meander through the countryside. The nearby Jug Bay Wetlands Sanctuary, part of the Patuxent River Park, features over 1,500 acres of tidal freshwater wetlands, forests, meadows, and fields. The sanctuary's trails and boardwalks allow visitors to explore this unique habitat and observe a wide array of plant and animal life. Birdwatchers will find Deale and its surroundings a paradise, with the Chesapeake Bay region being a critical stopover for migratory birds. The area's diverse habitats support over 300 species of birds throughout the year, making it a rewarding destination for both novice and experienced birders. For a more relaxed experience, Deale's local parks and beaches offer the perfect spots for picnicking, sunbathing, and simply enjoying the waterfront views. With its slower pace of life and natural beauty, Deale invites visitors to unwind and reconnect with the outdoors. Whether you're casting a line into the bay, exploring the wetlands, or watching the sunset over the water, Deale, Maryland, provides a natural sanctuary where the wonders of the Chesapeake Bay come to life.
Weather IconWeather in Deale
Deale, Maryland, nestled along the western shore of the Chesapeake Bay, offers a classic Mid-Atlantic climate with four distinct seasons that each bring their own appeal to visitors and locals alike. The summer months, from June through August, are warm and humid, with temperatures often climbing into the high 80s to low 90s Fahrenheit (around 30-34°C). This is the time when the Chesapeake Bay becomes a hub of activity, with boating, fishing, and water sports taking center stage. The humidity can be high, but the proximity to the water often brings a refreshing breeze. Thunderstorms are not uncommon in the afternoons, contributing to the overall precipitation. Autumn, from September to November, is a particularly pleasant time to visit Deale. The heat and humidity of summer begin to wane, giving way to cooler temperatures that average from the mid-50s to low 70s Fahrenheit (around 13-22°C). This season is less rainy than the summer, and the changing leaves provide a beautiful backdrop for outdoor activities like hiking and exploring the local wildlife. Winter, from December through February, is cooler with temperatures ranging from the low 30s to mid-40s Fahrenheit (around 0-7°C). Snow is possible, though not as heavy or frequent as in more northern regions. The crisp winter air and occasional frosty mornings offer a quiet and serene landscape, ideal for those who appreciate a peaceful retreat. Spring, from March to May, sees a gradual warming with temperatures that can range from the upper 40s to the high 60s Fahrenheit (around 9-20°C). This is a time of renewal, with blossoming flowers and budding trees. Rainfall is moderate, and the fresh spring air is perfect for outdoor pursuits like bird watching and enjoying the local parks. The most popular weather conditions in Deale are typically found in the late spring through early fall, when the temperatures are warm but not excessively hot, and the outdoor activities around the Chesapeake Bay are at their best. Late September to early October is especially pleasant, as the summer crowds have thinned, the humidity has dropped, and the beauty of autumn begins to unfold. Whether you're looking to sail on the bay, enjoy fresh seafood, or simply relax by the water's edge, Deale offers a charming escape with a climate that caters to a variety of interests throughout the year.
Transportation in Deale
Deale, Maryland, is a charming waterfront community located on the western shore of the Chesapeake Bay. This serene destination is not served by major airports or train stations directly, but it is still accessible through various means. Travelers typically arrive in the region by flying into Baltimore-Washington International Thurgood Marshall Airport (BWI), which is the nearest major airport, located about an hour's drive away. From BWI, renting a car is the most convenient option for reaching Deale, providing the freedom to explore the surrounding areas at your own pace. Alternatively, ride-sharing services and taxis are available at the airport, though they may be more costly for the distance to Deale. For those who prefer to drive, Deale is accessible via major highways and scenic byways. It's a straightforward drive from cities like Baltimore, Washington D.C., and Annapolis, making it a popular choice for a peaceful getaway from urban life. Once in Deale, the transportation options are limited. The area does not have a public transportation system, so having a car is essential for getting around. The community is spread out, and while there are marinas, restaurants, and shops, they are not typically within walking distance of each other. For boating enthusiasts, Deale is a dream destination, with numerous marinas offering slips and services for personal watercraft. For those who enjoy cycling, bringing a bike can be a pleasant way to explore the local area, as the traffic is generally light on the backroads, and the scenery is beautiful. However, for day-to-day travel and visiting local attractions, a car remains the most practical mode of transportation. In terms of walkability, Deale is not considered a walkable destination due to the distances between points of interest and the lack of sidewalks in many areas. It's a place where the enjoyment of the natural environment, boating, and leisurely drives take precedence over pedestrian exploration. In conclusion, while Deale may not have the transportation infrastructure of a major city, its accessibility by car and the tranquility it offers make it a worthwhile destination for those looking to enjoy the Chesapeake Bay's natural beauty and maritime charm.