Annapolis vacation rentals

We found 725 vacation rentals — enter your dates for availability

Select from 377 houses, 26 condos, and other vacation rentals to find the perfect place for your stay in Annapolis. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a garden and pool. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Annapolis

Showing deals for:Jun 12 - Jun 19

Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

View from the front of this Stately Masterpiece (you'd think I built it ;-)
8.0 out of 10, Very Good, (5 reviews)
Very Good
(5 reviews)

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Annapolis

17% off
Price is $974
$6,816 for 7 nights
All fees included
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

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Find out more about Annapolis

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnyModerately LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyModerately LowSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageAverage
June73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighSlightly High
August76.8°F (24.9°C)Light RainMostly SunnyModerately HighSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

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.

Unlock savings with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on your entire booking. Being the organizer certainly has its perks. By joining our OneKey rewards program, you can unlock exclusive discounts and accumulate OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

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)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Compass Pointe Golf Courses (11 mi / 17.7 km)
  • Queenstown Harbor Golf Club (17.4 mi / 28 km)
  • Queenstown Harbor Golf Links (17.4 mi / 28 km)
  • St. Michaels Winery (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:

  • Carrs Beach (2 mi / 3.3 km)
  • 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)
  • Allen Pond Park (13.4 mi / 21.5 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.

Frequently asked questions

What is the best area to stay in Annapolis, Maryland, United States of America when booking a vacation rental?
When looking for the best area to stay in Annapolis, Maryland, one highly recommended neighborhood is the historic downtown area. This vibrant district is known for its charming streets lined with historic architecture, and it offers easy access to waterfront views. You'll find a variety of vacation rental options, from cozy apartments to larger homes, providing a great base for exploring the city.

In addition to the picturesque surroundings, downtown Annapolis is home to top attractions such as the United States Naval Academy, where you can take guided tours and learn about its rich history. The nearby City Dock is another must-visit spot, superb for enjoying waterfront dining and watching the boats go by.

Another appealing neighborhood is Eastport, which is just across the bridge from downtown. This area has a more laid-back vibe, with a strong sense of community and several delightful local eateries. You can easily stroll to the Annapolis Maritime Museum to delve into the area's maritime heritage, and the proximity to the water makes it ideal for sailing enthusiasts.
How much does it cost to rent a vacation home in Annapolis?
Prices for vacation rentals in Annapolis vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Annapolis to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Annapolis vacation house rentals?
You can find great discounts on house rentals in Annapolis on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Annapolis?
For renting a beach house in Annapolis, consider the picturesque areas along the Chesapeake Bay. The Broadneck area, known for its waterfront charm, offers several vacation rentals with direct access to sandy beaches and stunning bay views. Many of these properties come equipped with amenities such as private docks, outdoor patios, and fully stocked kitchens, great for families or groups looking to enjoy a seaside retreat.

Additionally, the Eastport neighborhood, just a short distance from downtown Annapolis, features a variety of rentals that blend coastal living with urban convenience. Here, travelers can find homes with spacious decks for entertaining, proximity to local restaurants and shops, and some even offer kayaks or bicycles for exploring the nearby waterfront.

The area around Sandy Point State Park is another great option, where beach houses often provide easy access to the park's sandy beaches, picnic areas, and hiking trails. Many properties in this region also feature outdoor grills and fire pits, ideal for evening gatherings after a day of fun in the sun.
Are there any houseboat rentals in Annapolis?
In Annapolis, there are several houseboat rentals available, primarily located along the picturesque waterfront area near the historic district and the Annapolis Harbor. These unique accommodations often feature amenities such as fully equipped kitchens, comfortable living spaces, and outdoor decks for enjoying the beautiful views of the water and city skyline. Many houseboats also provide easy access to local attractions like the United States Naval Academy and the Maryland State House, making them an appealing choice for travelers looking to experience the charm of this maritime city from a distinctive perspective. See all houseboats in Annapolis.
What is the most popular type of vacation rental accomodation in Annapolis?
In Annapolis, vacation houses are the most popular type of rental, with around 301 available throughout the area. These homes are often situated in charming neighborhoods, providing easy access to local attractions such as the historic downtown, the Naval Academy, and the scenic waterfront. Most vacation houses come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces like decks or patios for enjoying the pleasant Maryland weather.

Additionally, there are about 45 apartments, 22 condos, and another 22 cottages available, suiting travelers looking for smaller accommodations. These options typically include modern amenities, such as Wi-Fi, laundry facilities, and many feature views of the harbor or nearby parks. For a great experience, there are several houseboats available, offering a distinctive stay on the water.
Are there any family house rentals in Annapolis?
In Annapolis, there are numerous family-friendly house rentals available, with around 257 options scattered throughout the city. Visitors can find accommodations in charming neighborhoods such as Murray Hill and Eastport, both rich in local character and close to attractions. Many homes in these areas come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can safely play.

Amenities like Wi-Fi and air conditioning are commonly found, ensuring a comfortable stay for guests. The proximity to the waterfront allows for easy access to activities like sailing or visiting the historic Annapolis Harbor, while the vibrant downtown area offers restaurants, shops, and cultural sites such as the Maryland State House.
Can I rent a vacation home with a pool or hot tub in Annapolis?
In Annapolis, there are many vacation homes available for rent that come equipped with pools or hot tubs, with about 38 options to choose from. This picturesque city, known for its historic charm and waterfront views, offers rentals in various neighborhoods, including the lively downtown area and the serene outskirts near the Chesapeake Bay.

Travelers can expect a range of amenities in these properties, including private swimming pools, relaxing hot tubs, and outdoor spaces for lounging and dining. Many homes also feature fully equipped kitchens, allowing for convenient meal preparation, and spacious living areas designed for comfort. Proximity to local attractions, such as the U.S. Naval Academy and the scenic waterfront, adds to the appeal of choosing a vacation rental in Annapolis. Find your rental in Annapolis with a pool or a hot tub.
Can I find long-stay vacation rentals in Annapolis?
A long-stay vacation rental in Annapolis is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Annapolis?
In Annapolis, travelers will find a variety of pet-friendly house rentals that cater to different needs and preferences. With around 149 options available, visitors can choose from charming homes in historic neighborhoods like the Eastport area, known for its waterfront views and close proximity to downtown Annapolis. Many of these rentals come equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and cozy living areas, making them ideal for families and groups traveling with pets.

The area is also home to several parks and green spaces that are great for pet owners. Quiet Waters Park features walking trails and scenic landscapes, offering a relaxing environment for outdoor activities with pets. Additionally, the nearby Broadneck Park has open fields and walking paths, providing ample space for dogs to roam and play.
Are there any remote work vacation rentals in Annapolis?
In Annapolis, there is a substantial selection of remote work vacation rentals, with about 373 options available. This historic city, known for its waterfront views and vibrant maritime culture, offers a variety of properties that cater to remote workers. Many rentals come equipped with dedicated workspaces, including desks and ergonomic chairs, ensuring a comfortable work environment. High-speed Wi-Fi is commonly available, and some properties even feature additional amenities such as printers for those needing to print documents.

Travelers can enjoy the scenic beauty of the Chesapeake Bay while also having easy access to local attractions, including the Maryland State House and the United States Naval Academy. The charming downtown area is filled with shops, galleries, and restaurants, providing a great balance between work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Annapolis vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Annapolis with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Annapolis?
In Annapolis, vacation rentals frequently feature amenities that enhance the stay for travelers. Most rentals come equipped with a kitchen, allowing guests to prepare their own meals, which is particularly useful for families or those wanting to save on dining out. Many properties also include a deck or patio, superb for enjoying a morning coffee or evening relaxation. A coffee or tea maker is commonly available, adding to the convenience of home-like comfort. Onsite parking is another popular amenity, which is particularly beneficial given the city's charm and attractions.
When is the best time to visit Annapolis for a vacation rental?
The most popular time to visit Annapolis for a vacation rental is during the peak season from May to July. This vibrant period draws a multitude of travelers eager to experience the city's rich maritime history, charming waterfront, and delightful festivals. Visitors can enjoy pleasant weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, making it ideal for outdoor activities like sailing, walking along the historic streets, or dining al fresco at waterfront restaurants.

July stands out as the pinnacle of tourist activity, offering a lively option filled with events such as the annual Annapolis Arts & Crafts Festival. This month is superb for those looking to immerse themselves in the local culture while exploring the picturesque harbor and engaging in water sports.

For those seeking a more budget-friendly option, consider visiting in November. This quieter month allows you to enjoy Annapolis' charm without the hustle and bustle of the peak season. You can explore the city's historic sites and enjoy the local cuisine at a more leisurely pace, all while experiencing the beautiful fall scenery.

Ultimately, your choice of when to visit Annapolis will depend on whether you prefer the lively energy of peak summer or the peaceful ambiance of the shoulder months.
How early should I book a Annapolis vacation rental?
Book your Annapolis vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Annapolis, Maryland, United States of America?
In Annapolis, visitors can explore a variety of attractions that highlight the city's rich maritime history and vibrant culture. The Historic District is a must-see, featuring charming historic architecture and landmarks such as the Maryland State House, which is the oldest state capitol still in continuous legislative use. Here, vacation rentals often provide easy access to local shops, restaurants, and waterfront views.

Another significant area is the U.S. Naval Academy, where guests can take guided tours to learn about its storied past and view impressive buildings like the Chapel and the Naval Academy Museum. The nearby City Dock offers picturesque views of the harbor and is bustling with activity, featuring restaurants, bars, and opportunities for boating and sailing.

For those interested in outdoor activities, the Broadneck area and the nearby Sandy Point State Park provide scenic trails, picnic areas, and access to the Chesapeake Bay, ideal for nature lovers and families.
Can I change or cancel my Annapolis home rental booking on Vrbo?
To find Annapolis vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Annapolis vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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