Annapolis, Maryland Vacation Rentals

Explore 115 rental homes and villas in Annapolis, 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 $124 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.

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Annapolis Overview
Nestled on the shimmering shores of the Chesapeake Bay, Annapolis, Maryland, beckons travelers with its enchanting blend of colonial heritage and nautical charm. As the state's capital and a treasure trove of American history, Annapolis boasts a beautifully preserved historic district where the cobblestone streets are lined with 18th-century buildings, including the illustrious Maryland State House, a beacon of American history as the former national capital. Annapolis is affectionately known as "America's Sailing Capital," and its maritime spirit is ever-present along its bustling waterfront. Here, visitors can immerse themselves in the sailing culture, whether by embarking on a scenic boat tour, taking sailing lessons, or simply savoring fresh seafood while watching the ballet of yachts and sailboats from a waterfront café. The prestigious United States Naval Academy stands proudly in Annapolis, offering guided tours that reveal the life of midshipmen and the rich tapestry of naval history. The campus is a visual feast, with its grand Beaux-Arts architecture and serene riverfront vistas. Art and culture thrive in Annapolis, with a vibrant arts district that showcases the creativity of local artists. The city's calendar is dotted with cultural festivals that celebrate everything from music and film to art, infusing the streets with energy and excitement. For those seeking tranquility, Quiet Waters Park offers serene trails for hiking or biking, idyllic picnic spots, and stunning views of the South River. Beach lovers will delight in the golden sands of Sandy Point State Park, where the panoramic views of the iconic Chesapeake Bay Bridge are truly unforgettable. The culinary scene in Annapolis is a feast for the senses, with a focus on the bounty of the Chesapeake Bay, especially the famed Maryland crabs. The city's breweries also offer a taste of local craftsmanship, with a selection of unique craft beers. Enhancing the Annapolis experience, imagine the luxury of staying in a private home, a haven where you can unwind in your own space after a day of exploration. Many of these homes offer the added indulgence of swimming pools, perfect for a refreshing dip on a warm day. With a variety of pet-friendly options, even your furry companions can join in the adventure. The allure of Annapolis is not just in its attractions but in the complete immersion of its lifestyle, best experienced through the comfort and intimacy of a home away from home. Annapolis is not just a destination; it's an experience that seamlessly weaves together history, maritime adventure, natural splendor, and cultural richness, ensuring that every visitor leaves with memories as lasting as the tides.
Cultural Attractions in Annapolis
Annapolis, Maryland is a cultural haven that will undoubtedly charm those who appreciate arts, history, and local traditions. The city boasts a dynamic arts scene with an abundance of museums, art galleries, and live music venues to discover. Start your adventure at the Annapolis Maritime Museum & Park for a glimpse into the city's maritime past. The Banneker-Douglass Museum, Maryland's official museum of African American heritage, houses a collection that spans centuries. Art lovers will be drawn to the Annapolis Arts District. This lively neighborhood is home to numerous artist studios and galleries featuring works from local and international artists. Live music is alive and well in Annapolis. Venues like Rams Head On Stage offer performances ranging from rock to jazz. The city also hosts the annual Annapolis Jazz Festival which draws musicians from across the nation. Experience local traditions by attending one of Annapolis' many annual events. The Maryland Renaissance Festival brings to life a 16th century European village complete with crafts, food, live performances on 8 stages and a jousting arena. Additionally, the U.S Naval Academy in Annapolis offers guided tours providing insights into midshipman life. Lastly, make sure to explore Historic Downtown Annapolis filled with historic buildings dating back to the 17th century. Here you can visit landmarks such as Maryland State House - the oldest state capitol still in continuous legislative use - and Hammond-Harwood House - an architectural masterpiece from colonial times. In summary, every corner turned unveils a new piece of history or breathtaking work of art making Annapolis an ideal destination for cultural enthusiasts.
Kids IconFamily friendly activities in Annapolis
Annapolis, Maryland, is indeed a charming place for families with children. The city's rich historical background and stunning natural landscapes offer a wide range of stimulating activities for younger tourists. Begin your journey at the Annapolis Maritime Museum & Park, an educational hub where children can gain insights into the city's maritime past and the ecology of Chesapeake Bay. The museum provides interactive displays and hands-on activities that make learning enjoyable. Next on the list is the Maryland State House, which holds the distinction of being the oldest state capitol still in continuous legislative use. Here, children can delve into American history and witness where George Washington resigned his commission as commander-in-chief of the Continental Army. For outdoor enjoyment, Quiet Waters Park is a perfect choice. This picturesque park offers numerous activities for children such as playgrounds, hiking trails, and even an ice skating rink during winter. The park also houses a Visitor Center featuring art galleries and a cafe. The Chesapeake Children's Museum is another must-see destination in Annapolis. This museum aims to foster an environment of discovery about oneself, the peoples, technologies, and ecology of the Chesapeake Bay area. Lastly, embark on a Pirate Adventures on the Chesapeake tour. This family-oriented boat tour takes you on an authentic pirate adventure packed with exciting activities like treasure hunting and water cannon battles. Annapolis also boasts plenty of child-friendly dining options. From seafood restaurants serving renowned Maryland crab to quaint ice cream shops offering homemade delicacies - there's something to please every taste bud. In Annapolis, there are abundant opportunities for children to learn while having fun - whether it's delving into history at one of its many museums or appreciating nature in its beautiful parks.
Nature IconOutdoor activities in Annapolis
Annapolis, Maryland, is a haven for nature enthusiasts and outdoor activity lovers. The city is located near the Chesapeake Bay, on the Severn River, offering numerous water-based activities such as sailing, fishing, kayaking and paddleboarding. The bay area also provides breathtaking views and hosts a variety of wildlife. Quiet Waters Park is an ideal spot for hiking enthusiasts. This 340-acre park has six miles of trails that meander through forests and past grassy fields and wetlands. It offers stunning views of the Severn River. The Baltimore & Annapolis Trail is another excellent hiking location. This 13-mile trail traces the route of the Annapolis and Baltimore Short Line Railroad, taking you through woodlands, urban areas and suburban communities. Bird-watchers should not miss Sandy Point State Park. Situated on the western shore of the Chesapeake Bay, this park is home to some waterfowl species and other birds. It's also a great spot for fishing and picnicking. For a unique outdoor experience, consider taking a boat tour to explore the many rivers and creeks that feed into the Chesapeake Bay. These tours provide an intimate look at the bay's ecosystem with chances to see wildlife such as bald eagles, ospreys and herons. Lastly, exploring downtown Annapolis by foot should not be missed. The city's historic district features charming brick-lined streets lined with 18th-century buildings that are perfect for leisurely strolls. In conclusion, whether you're into hiking or bird-watching or simply enjoy being by the water, Annapolis offers plenty to nature lovers with its proximity to both riverine landscapes and Chesapeake Bay region.
Weather IconWeather in Annapolis
Annapolis, Maryland is characterized by a humid subtropical climate, resulting in hot, humid summers and mild to cool winters. This climate is influenced by its proximity to the Chesapeake Bay, which often moderates temperatures and adds to the humidity. During the summer months of June through August, Annapolis experiences warm weather with average high temperatures reaching the upper 80s Fahrenheit. These months are also marked by high humidity and increased rainfall. Thunderstorms are frequent during this period but typically pass quickly. Winter in Annapolis spans from December to February and is generally mild with average high temperatures in the mid-40s Fahrenheit. However, there can be colder spells with temperatures occasionally dropping below freezing at night. Snowfall does occur but it's not a common phenomenon in Annapolis. Spring and fall seasons offer more moderate temperatures and reduced humidity making them particularly enjoyable times for a visit. Springtime runs from March to May with temperatures ranging from the mid-50s to low 70s Fahrenheit while fall extends from September to November offering similar conditions along with vibrant foliage that adds color to the city's landscapes. Visitors tend to favor spring and fall due to comfortable weather conditions ideal for outdoor activities such as sailing or exploring the city's historic district on foot. Nonetheless, each season has its own unique charm offering visitors diverse experiences throughout the year.
Transportation in Annapolis
Annapolis, Maryland, is a city that provides a diverse range of transportation choices for its visitors. The majority of travelers reach Annapolis by air, landing at the Baltimore/Washington International Thurgood Marshall Airport which is roughly 25 miles away from the city. From there, numerous options are available to get to Annapolis such as taxis, shuttles and ride-sharing services like Uber and Lyft. Annapolis is also easily accessible by road for those who prefer this mode of travel. It's conveniently situated near several major highways and there are bus services provided by Greyhound and Megabus that link Annapolis with other significant cities. Once you've arrived in Annapolis, navigating around the city is straightforward. The city runs a public transportation system called Annapolis Transit which includes buses that service various routes throughout the city. Taxis and ride-sharing services are also readily available. For those who enjoy exploring at their own leisurely pace, bike rentals can be found in the downtown area. This can be a delightful way to take in the sights particularly during the warmer months. The downtown area of Annapolis is known for its compactness making it highly walkable for visitors. Many of the city's attractions including the United States Naval Academy, Maryland State House and historic district are within walking distance from each other. However, if you're planning to visit destinations outside of downtown or nearby areas like Sandy Point State Park or Chesapeake Bay Bridge, using public transport or a car would be necessary. To sum up, whether you're reaching Annapolis by air or road and planning to explore the city by bus, car or on foot; Annapolis offers an array of options that meet every traveler's requirements.