Annapolis holiday lettings

Why visit Annapolis

• Historic charm: Annapolis is rich in history, featuring well-preserved historic houses and landmarks that tell tales of its past.
• Scenic waterfront: The city boasts beautiful marinas and waterfront parks, perfect for leisurely walks and outdoor activities.
• Family-friendly attractions: There are numerous activities suitable for families, ensuring a delightful experience for visitors of all ages.
• Vibrant downtown: The lively downtown area offers shopping, dining, and cultural experiences, ideal for leisurely exploration.
• Outdoor adventures: Nearby Kent Island provides a gateway to various outdoor pursuits, from hiking to water sports.

Popular types of accommodation in Annapolis

At Vrbo, we offer a variety of accommodations in Annapolis to suit every traveller's needs. Whether you're seeking a charming private holiday home, a cozy cottage, or a stylish apartment, you'll find the perfect place to stay in Annapolis. Explore our selection of house rentals and condo rentals, and enjoy a memorable getaway with family or friends in this beautiful coastal city.

• Houses: The top choice for visitors to Annapolis, offering spacious and comfortable accommodations perfect for families or groups of friends.
• Cottages: A delightful option for a quaint and charming retreat, ideal for those seeking a peaceful getaway.
• Apartments: A convenient and modern choice, providing the comforts of home in the heart of the city.
• Condos: A stylish alternative, often featuring amenities like pools and fitness centres, perfect for a relaxing stay.
• Villas: Luxurious accommodations that offer ample space and high-end features for an indulgent holiday experience.**

Top attractions in Annapolis

Annapolis is perfect for families and those seeking a city-themed or outdoor getaway. Visitors can enjoy an array of attractions, including urban parks, marinas, and historic houses. The points of interest in and around Annapolis provide excellent opportunities for outdoor activities, cultural experiences, and family-friendly fun, ensuring there's something for everyone to enjoy during their stay.

• U.S. Naval Academy: A historic institution showcasing military tradition and stunning architecture. Explore the beautiful grounds and visit the Naval Academy Museum for a glimpse into the naval heritage of the United States.
• Chesapeake Bay Bridge: An impressive modern marvel that offers breathtaking views of the bay. Experience the vibrant city vibes as you walk or drive across this iconic structure, linking Maryland's eastern and western shores.
• Sandy Point State Park: A delightful national park perfect for outdoor adventures. Enjoy hiking, picnicking, and stunning waterfront views, making it an ideal spot for nature lovers and families alike.

Things to do recommended for couples

For a romantic getaway in Annapolis, embark on a sailing adventure with the Annapolis Sailing School, indulge in a captivating performance at the Ballet Theater of Maryland, or enjoy a delightful wine tasting at Thanksgiving Farm Wines, located a mere 6.2km away. Perfect for couples seeking memorable experiences!

Things to do recommended for families

Families visiting Annapolis can immerse themselves in the sports atmosphere at the Navy-Marine Corps Memorial Stadium, enjoy thrilling games at the Annapolis Bowl arcade, and unwind at Fort Smallwood Park, a serene spot just 6.8km away, perfect for relaxation and wellness activities.

Things to do recommended for groups

Groups visiting Annapolis can indulge in a shopping spree at the Westfield Annapolis Mall, enjoy a round of golf at the nearby Bay Hills Golf Club, or experience local culture and romance at The Colonial Players theatre, ensuring a delightful blend of activities for everyone.

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

If you're travelling with a group, family, pets, or seeking longer stays, be sure to refine your search based on your key preferences. Here are some helpful Vrbo booking tips for you.

• Traveling to Annapolis with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for these options and much more on Vrbo.
• Traveling to Annapolis with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, as well as seek out age-appropriate facilities, 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, a family holiday wouldn't feel complete without their furry companion by their side. If you can relate to this, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations 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 holiday rentals that offer discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Annapolis

Annapolis, a charming city steeped in history, offers delightful experiences for families and city explorers alike. The vibrant downtown is perfect for leisurely strolls, while nearby Kent Island invites outdoor adventures. The Annapolis area is renowned for its friendly atmosphere and rich heritage, ensuring a memorable holiday filled with excursions and family-friendly activities. Discover the ideal blend of relaxation and exploration in this captivating destination.

• Historic District: Nestled in the heart of Annapolis, the Historic District offers visitors a charming blend of history and modernity. With its cobblestone streets and colonial architecture, this area invites you to explore its rich heritage. Families will enjoy leisurely strolls while uncovering local landmarks such as the academy and the bustling dock port. The district is also a hub for shopping, featuring quaint boutiques and a vibrant shopping mall centre, perfect for those seeking a unique retail experience.
• Parole: Located near Annapolis, Parole is a quaint village that caters to families and business travellers alike. This community boasts a range of educational facilities and a prominent shopping centre, ensuring that visitors have everything they need at their fingertips. Notable attractions include a pristine beach and a local stadium, making it an excellent spot for sports enthusiasts. Parole provides a delightful atmosphere for both relaxation and exploration, all within easy reach of Annapolis.
• Eastport: Just a stone's throw from Annapolis, Eastport is a vibrant neighbourhood known for its outdoor activities and family-friendly environment. The area features a mix of educational facilities and recreational spaces, encouraging visitors to engage with nature. Highlights include the scenic beach and a lively tourist precinct, which is perfect for soaking in the local culture. Eastport's charming waterfront adds to its allure, making it an ideal destination for those looking to immerse themselves in the beauty of the Chesapeake Bay.

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 upcoming journey? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a dedicated area to craft new trips, pick up from where you last paused, or review and manage your travel plans. You can easily locate properties you've previously saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.