Annapolis holiday homes

Why visit Annapolis

• Historic charm: Annapolis boasts a rich history with its beautifully preserved colonial architecture and vibrant downtown, perfect for leisurely exploration.
• Waterfront activities: Enjoy scenic views and a range of water-based activities at the picturesque marinas and parks along the waterfront.
• Cultural experiences: Immerse yourself in local culture through art galleries, museums, and community events that highlight Annapolis’s heritage.
• Family-friendly atmosphere: The city offers numerous parks and family-oriented activities, making it an ideal destination for visitors of all ages.
• Walkable city: Annapolis’s compact layout encourages visitors to explore on foot, discovering charming streets and hidden gems along the way.

Top attractions in Annapolis

Annapolis in Maryland offers a delightful blend of urban parks, marinas, and historic houses, perfect for a family or outdoor holiday. Explore its charming streets and immerse yourself in the city’s rich heritage and culture, all within a picturesque, walkable setting. Annapolis is ideal for travellers seeking a vibrant, historical city experience with plenty of opportunities for outdoor adventures.

• Sandy Point Beach: Enjoy the beach vibes with splendid sandy shores perfect for a leisurely stroll or a refreshing dip in the water.
• Annapolis Maritime Museum: Immerse yourself in local maritime culture, exploring maritime artefacts that tell the rich seafaring history of the city.
• Bay Ridge Beach: Revel in the coastal charm with pristine beachscapes ideal for relaxation and scenic seaside moments.

Things to do recommended for couples

Experience the charm of Annapolis with a romantic harbour cruise, delightful waterfront dining and a leisurely stroll through historic streets, perfect for couples seeking a unique local escape.

Things to do recommended for families

Families can explore the historic waterfront at the Annapolis City Dock, enjoy a day at the sandy Broadneck Park beach, or take a scenic sailboat tour on the Chesapeake Bay. Don't miss the interactive exhibits at the Maryland State House for a fun learning experience.

Things to do recommended for groups

Groups visiting Annapolis can experience a fascinating historic tour of the U.S. Naval Academy, enjoy a delightful seafood feast at the waterfront, and take a scenic sailing trip on the Chesapeake Bay to soak in the stunning views of the coastline.

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

Whether you're journeying with a group, as a family, with your furry mates, or seeking extended stays, ensure you filter using the appropriate criteria. Here are some Vrbo booking pointers for you.

• Traveling to Annapolis with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
• Traveling to Annapolis with young kids: Traveling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with finding 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, a family getaway wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and comfortable beds, ensuring that everyone feels at home.
• Planning for a long term stay visiting Annapolis: If you're on the hunt for holiday rentals with great deals for stays of a month or more, you've come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in and around Annapolis

Annapolis offers a rich historical vibe with its charming downtown and waterfront escape. Visitors can explore the city's storied streets, enjoy scenic views on the water, and immerse themselves in the family-friendly atmosphere that fills every neighbourhood. Whether you fancy a cultural stroll or a relaxing day by the water, Annapolis makes a brilliant destination for a memorable holiday experience.

• Homewood: Homewood is a vibrant neighbourhood located in proximity to Annapolis, offering visitors a delightful blend of sports, culture, and outdoor experiences. This community is ideal for those looking to engage in educational pursuits, enjoy local shopping, or partake in recreational activities. Highlights include access to a renowned sports facility stadium, where you can catch exciting games, as well as a charming local academy that fosters a love for learning. The area is perfect for those keen on exploring the outdoors while soaking in the local culture.
• Sherwood Forest: Nestled in the Annapolis area, Sherwood Forest is a picturesque village that caters to families and outdoor enthusiasts alike. Its inviting parks and green spaces offer a serene escape from the hustle and bustle of city life. Visitors can explore a nearby shopping centre for unique finds or enjoy recreational activities with family. The local urban park and stunning bay views provide ample opportunities for outdoor adventures, making it a perfect spot for picnics, hiking, and enjoying nature with loved ones.
• Edgewater: Just 8km from Annapolis, Edgewater is a charming city that captivates visitors with its stunning scenery and family-friendly atmosphere. The area boasts beautiful beaches and access to the bay, making it a fantastic destination for outdoor activities such as swimming, kayaking, and fishing. With a variety of educational and recreational venues, including local shopping centres, Edgewater is an ideal spot for families seeking a fun-filled day out or a leisurely weekend getaway.

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.

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

Booking with Vrbo is simple

Are you looking to save on your next adventure? Being flexible with your travel dates could be a game changer, as prices can fluctuate. You might also unlock substantial savings by opting for a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s innovative Trip Board offers you a place to build fresh itineraries, pick up where you last left off, or review and organise your plans. Any properties you’ve previously saved or booked are now neatly arranged in Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to 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

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

• Maryland Renaissance Festival (5.4 mi / 8.6 km)
• Thanksgiving Farm Wines (10.4 mi / 16.8 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)
• Laurel Park (20.3 mi / 32.7 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

• 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)
• Chesapeake Bay Environmental Center (14.3 mi / 23.1 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 16.8 mi (27 km) away.