Annapolis holiday rentals

Why visit Annapolis

• Historic District: Stroll through Annapolis' charming streets filled with well-preserved colonial architecture and historic landmarks.
• Vibrant Waterfront: Enjoy the scenic Annapolis harbour, perfect for leisurely walks, boat tours, and stunning views.
• Maritime Heritage: Immerse yourself in the city’s rich maritime history, with museums and maritime activities reflecting its nautical past.
• Cultural Experiences: Discover local art galleries and theatres showcasing the vibrant arts scene unique to Annapolis.
• Outdoor Adventures: Explore urban parks and outdoor spaces, ideal for families and nature lovers seeking recreation.

Popular types of accommodation in Annapolis

Planning a getaway to Annapolis, Maryland? This charming city, known for its rich maritime history and vibrant arts scene, offers a delightful array of holiday rental options, including private homes, cosy cottages, and stylish apartments. While you explore the historic district, the stunning waterfront, and iconic landmarks, enjoy the comfort and convenience of your chosen accommodation. Discover the perfect rental to enhance your Annapolis experience.

• Private Holiday Homes: Discover the charm of secluded retreats offering complete privacy and a homely feel in Annapolis.
• Cottages: Enjoy cosy, quaint dwellings with a touch of rustic appeal, ideal for a peaceful escape.
• Apartments: Opt for modern, well-equipped urban flats, perfect for experiencing city life in comfort.
• Condos: Experience stylish, contemporary living with shared amenities in a vibrant setting.
• Villas: Indulge in spacious, elegant residences that provide a luxurious and relaxing stay.**

Top attractions in Annapolis

Annapolis, Maryland offers a charming blend of urban parks, marinas, and historic houses, making it an ideal destination for families and outdoor enthusiasts. Explore the vibrant Annapolis harbour and immerse yourself in the city's rich culture and history. Whether you're enjoying leisurely walks or seeking cultural experiences, Annapolis promises memorable adventures in a picturesque setting.

• Chesapeake Bay Bridge: A modern bridge with city vibes, offering magnificent views and a seamless connection through Annapolis. Its sleek design stands out in the urban landscape.
• Sandy Point State Park: A national state park providing outdoor, scenic adventures and a breath of fresh air with its picturesque settings and ample space for exploration.
• Maryland State House: A historic civic government building exuding culture vibes, inviting visitors to appreciate its storied past and architectural splendour.

Things to do recommended for couples

Explore Annapolis with your loved one while strolling through historic streets, enjoying a boat ride on the water, and indulging in delightful harbour views, all offering a romantic escape in this charming town.

Things to do recommended for families

Families will delight in exploring the United States Naval Academy, where they can enjoy fascinating exhibits and tours. The nearby Chesapeake Bay offers opportunities for sailing and kayaking, while the historic downtown area boasts charming shops and eateries perfect for a leisurely family day out.

Things to do recommended for groups

Discover the maritime legacy and vibrant culture of Annapolis. Enjoy scenic harbour walks, savour local seafood delicacies and engage in interactive group activities that bring history and community to life.

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

Whether you are travelling with a group, as a family, with your pets, or seeking extended stays, be sure to filter by the appropriate priorities. Here are some Stayz booking tips for you.

• Traveling to Annapolis with a group: Consider how many bedrooms you require, along with facilities like a fully equipped kitchen or an outdoor area suitable for group gatherings. Fortunately, you can refine your search on Stayz to include all these features and more.
• Traveling to Annapolis with young kids: Traveling with young children can present its challenges. It is important to prioritise their comfort and safety, while also ensuring age-suitable facilities, such as a private swimming pool, are available. Additionally, considering your closeness to family-friendly attractions is advisable.
• Taking your pets with you to Annapolis: For many, a family holiday isn’t truly complete without their beloved pet by their side. If you can relate to this, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
• Planning for a long term stay visiting Annapolis: If you're seeking holiday lets with special offers for stays of a month or more, you've come to the right place. With the appropriate filter, you can effortlessly discover and secure savings on monthly rentals. You might also want to consider refining your search to include a parking space, a well-equipped kitchen, or a private pool.

Where to stay in and around Annapolis

Discover Annapolis, a charming state capital with a blend of historical allure and modern vibrancy. Wander through picturesque streets, explore family-friendly neighbourhoods, and enjoy outdoor excursions in the heart of the city. Experience the best of Annapolis with a mix of cultural gems and relaxing spots that capture the essence of this delightful urban retreat.

• Historic District: Nestled in the heart of Annapolis, the Historic District is a vibrant neighbourhood that encapsulates a rich tapestry of history and modern urban delights. Visitors can immerse themselves in a family-friendly, outdoorsy, city-themed experience, exploring educational landmarks such as an academy and a bustling tourist precinct. The area also offers a delightful shopping scene with both a shopping area and centre, alongside a picturesque dock port that whispers tales of maritime heritage.
• Arnold: Located a short 6km journey from Annapolis, Arnold is a charming city that invites travellers to savour scenic outdoor adventures and family-oriented activities. With an emphasis on education and leisure, the city boasts a well-regarded golf course and offers delightful experiences by the bay, a sandy beach, and a serene lake, making it a perfect spot for those who appreciate a blend of nature and recreation.
• Arundel on the Bay: Arundel on the Bay is a captivating neighbourhood that promises a refreshing mix of outdoor, beach, and scenic experiences. Situated conveniently within the Annapolis area, it is known for its inviting recreational areas and a bustling shopping centre. Visitors can enjoy the serene beauty of the nearby beach and bay while also exploring local educational landmarks like the academy, ensuring a culturally enriching and leisurely holiday for all.

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 Stayz is a breeze

Looking to cut costs on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. You might also secure substantial savings by planning a longer stay. To locate a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday let.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers a handy space to create new trips, resume where you previously left off, or review and arrange your plans. Your saved or booked properties are neatly organised into categories labeled Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.