Annapolis vacation rentals

Why visit Annapolis

• Historic Charm: Annapolis boasts a rich history with its well-preserved colonial architecture and historic sites, including the Maryland State House.
• Waterfront Activities: Enjoy a variety of outdoor adventures, from sailing and kayaking to leisurely strolls along the scenic waterfront.
• Cultural Experiences: The vibrant downtown area is filled with unique shops, galleries, and restaurants, perfect for exploring local culture.
• Family-Friendly Fun: With urban parks and family-oriented attractions, there are plenty of activities for visitors of all ages.
• Cozy Accommodations: Choose from charming vacation rentals and cozy cottages that offer a comfortable home base for your adventures.

Popular types of accommodation in Annapolis

When planning your getaway to Annapolis, you'll find a variety of popular vacation rental options to suit your needs. From charming houses and cozy cottages to modern apartments, there's something for everyone. Explore the best Maryland vacation rentals and enjoy a range of amenities that enhance your stay. Whether you're seeking a relaxing retreat or the comforts of home, Annapolis has the perfect spot for you, including options near the renowned Marriott Annapolis.

• Houses: The top choice for visitors in Annapolis, offering spacious and comfortable accommodations ideal for families or groups.
• Cottages: A charming and cozy option, perfect for a quaint getaway surrounded by nature.
• Apartments: A convenient choice for those seeking a home-like setting with easy access to local attractions.
• Condos: A stylish option featuring modern amenities, ideal for travelers wanting a bit more luxury.
• House Boats: For a unique experience, stay on the water and enjoy the scenic views of Annapolis.**

Top attractions in Annapolis

Annapolis is a fantastic destination for families and outdoor enthusiasts, offering a blend of city charm and natural beauty. Visitors can explore urban parks, historic houses, and marinas, making it an ideal spot for cultural experiences and family-friendly activities. Whether you're seeking relaxation or adventure, Annapolis has a variety of attractions to enhance your vacation experience.

• Chesapeake Bay Bridge: This iconic modern bridge offers stunning views of the Chesapeake Bay, connecting the Eastern and Western shores. Experience the vibrant city vibes as you cross this architectural marvel, perfect for photo ops and a sense of adventure.
• Sandy Point State Park: A haven for nature lovers, this national park features beautiful scenery and a range of outdoor activities. Enjoy hiking, picnicking, and stunning views of the bay, all set against a backdrop of lush landscapes.
• Annapolis City Dock: Rich in history, this picturesque dock features charming shops and waterfront dining. Stroll along the scenic paths, soak in the maritime culture, and enjoy views of the sailboats and historic ships.

Things to do recommended for couples

For a romantic getaway in Annapolis, consider visiting the Old South Country Club, located 14 miles away. Enjoy the luxurious ambiance while indulging in fine dining and picturesque views, perfect for creating lasting memories with your partner.

Things to do recommended for families

Families visiting Annapolis can explore the Maryland State House, enjoy interactive exhibits at the U.S. Naval Academy Museum, and take a scenic boat tour of the Chesapeake Bay. The city’s charming streets and waterfront parks provide endless opportunities for fun and relaxation for all ages.

Things to do recommended for groups

Explore the rich maritime history at the United States Naval Academy or enjoy a scenic sailing tour in the Chesapeake Bay. Don’t miss the vibrant local dining scene on West Street, perfect for group gatherings after a day of adventure.

What do I need to keep in mind when booking a vacation in Annapolis

When traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

• Traveling to Annapolis with a group: Think about how many bedrooms you'll require and any additional features you might want, like a complete kitchen or outdoor space for gatherings. Luckily, you can easily apply filters for all of these options and more on Vrbo.
• Traveling to Annapolis with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Annapolis: For many families, a trip isn’t truly complete without their furry companion. If this resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Annapolis: If you’re in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the right filters, you can quickly discover and save on monthly rental options. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Annapolis

Annapolis, Maryland, is a charming city perfect for family-friendly vacations, outdoor adventures, and historical exploration. While you enjoy the vibrant downtown area with its unique shops and restaurants, consider nearby destinations that offer a relaxing atmosphere and friendly locals. From cozy Annapolis vacation rentals to exciting excursions, this area promises an unforgettable travel experience tailored to your interests. Book your trip today and immerse yourself in the rich culture and scenic beauty of Annapolis.

• Historic District: The Historic District of Annapolis is a charming neighborhood that immerses visitors in the city's rich maritime history. Located around the heart of Annapolis, this area is ideal for families and outdoor enthusiasts seeking a vibrant city atmosphere. Stroll through the picturesque streets lined with colonial architecture, where you'll find various shops and educational venues. Notable attractions include the United States Naval Academy, the bustling tourist precinct, and the scenic dock port, perfect for leisurely walks and waterfront dining.
• Parole: Parole is a quaint village situated near Annapolis, offering a delightful blend of family-friendly activities and business conveniences. Visitors can explore numerous shopping centers and malls, making it an excellent spot for retail therapy. The area is also home to educational institutions and features beautiful parks, including scenic lakes and urban green spaces. With its easy access to Annapolis attractions and a welcoming atmosphere, Parole is a great place to unwind while still being close to the city's vibrant energy.
• Eastport: Nestled along the water's edge, Eastport is a lively neighborhood known for its outdoor activities and family-oriented experiences. Just a stone's throw from Annapolis, this area boasts scenic views of the bay and access to beautiful beaches. Visitors will enjoy various shopping options and recreational venues, including a golf course. Key highlights include the local academy and the stunning waterfront, which provides ample opportunities for sailing, kayaking, and enjoying the sun. Eastport's unique blend of urban charm and natural beauty makes it a must-visit destination.

Best time to go to Annapolis

If you're planning a trip to Annapolis, 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 January to March tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	37.9°F (3.3°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
March	44.6°F (7.0°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
April	55.0°F (12.8°C)	Light Rain	Mostly Sunny	Average	Average
May	64.2°F (17.9°C)	Light Rain	Mostly Sunny	Average	Average
June	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	76.8°F (24.9°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	70.7°F (21.5°C)	Light Rain	Mostly Sunny	Average	Average
October	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
November	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Average	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Average	Average

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area for you to plan new trips, manage your ongoing plans, or review and organize your existing bookings. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Historic Annapolis will entice you

The area's history and live music are just a few of the reasons to vacation in Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. 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 and around Annapolis

Are you searching for things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Annapolis a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

• Maryland Renaissance Festival (5.4 mi / 8.6 km)
• Thanksgiving Farm Wines (10.4 mi / 16.8 km)
• Renditions Golf Club (10.7 mi / 17.3 km)
• Queenstown Harbor Golf (17.4 mi / 28 km)
• St. Michaels Winery (19.9 mi / 32.1 km)
• Chesapeake Beach Water Park (19.9 mi / 32.1 km)

Exploring the natural landscape of Annapolis

Whether you're an active traveler or just want to appreciate the scenery, Annapolis is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

• Maryland Quiet Waters Park (2.4 mi / 3.9 km)
• Bay Ridge Beach (2.9 mi / 4.6 km)
• Sandy Point Beach (5.7 mi / 9.2 km)
• Northern Chesapeake Bay (8 mi / 12.8 km)
• Fort Smallwood Park (11 mi / 17.6 km)
• Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)

Transportation to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Baltimore Washington Intl. Airport (BWI), which is 16.8 mi (27 km) away.