Annapolis vacation rentals

We found 703 vacation rentals — enter your dates for availability

Select from 373 houses, 54 apartments, 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:Mar 27 - Apr 3

Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland

Marina
9.8 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville

13% off
Price is $276
$1,930 for 7 nights
All fees included
Chesapeake Houseboat Getaway on Kent Island, Maryland

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Find out more about Annapolis

Why visit Annapolis

  • Historic Exploration: Wander through Annapolis' picturesque historic district, rich in colonial architecture and landmarks.
  • U.S. Naval Academy: Visit this iconic military academy to learn about naval history and enjoy its beautiful campus.
  • Waterfront Activities: Embrace the scenic waterfront with opportunities for dining, boating, and relaxing by the water.
  • Family-Friendly Fun: Enjoy a variety of family-oriented activities, ensuring fun for all ages.
  • Diverse Accommodations: Choose from charming inns to modern hotels, catering to every traveler's needs.

Popular types of accommodation in Annapolis

If you're planning a getaway to Annapolis, you're in for a treat. Our most popular vacation rental options include houses, cozy cottages, and stylish apartments. Whether you're looking for spacious house rentals, modern condo rentals, or charming vacation rentals, Annapolis has something to suit every traveler's needs. Discover the perfect place to unwind and enjoy all that this historic city has to offer.

  • Houses: The top choice for visitors in Annapolis, offering spacious and comfortable settings, ideal for families or groups.
  • Cottages: A charming option for those seeking a cozy and picturesque stay, perfect for a romantic getaway or a peaceful retreat.
  • Apartments: A convenient and flexible choice, providing all the essential amenities for a comfortable urban experience.
  • Condos: Stylish and modern, these rentals offer great locations and community amenities for a vibrant vacation.
  • House Boats: For a unique experience, these floating accommodations allow you to enjoy the waterfront lifestyle in Annapolis.**

Top attractions in Annapolis

Annapolis, Maryland, is a fantastic destination for families and outdoor enthusiasts alike, offering a blend of urban parks, marinas, and historic houses to explore. Whether you're interested in cultural experiences or family-friendly activities, there's something for everyone in this charming city. Be sure to take advantage of the scenic waterfront and immerse yourself in the rich history that Annapolis has to offer during your visit.

  • U.S. Naval Academy: A historic institution with stunning architecture and scenic views, offering guided tours that highlight its rich naval heritage and traditions.
  • Chesapeake Bay Bridge: An engineering marvel that connects Annapolis to the Eastern Shore, providing spectacular views of the bay and a vibrant city atmosphere.
  • Sandy Point State Park: A beautiful national park featuring sandy beaches, hiking trails, and recreational activities, perfect for outdoor adventures and enjoying nature.

Things to do recommended for couples

For a romantic getaway in Annapolis, consider sailing together at Annapolis Sailing School for outdoor adventure, enjoying a captivating performance at the Ballet Theater of Maryland, or savoring fine wines at Thanksgiving Farm Wines, just 10 miles away, perfect for a cozy, intimate experience.

Things to do recommended for families

Your family can enjoy an exciting day at the Navy-Marine Corps Memorial Stadium, filled with sports vibes. For some arcade fun, visit Annapolis Bowl, perfect for adventure seekers. Don't miss Fort Smallwood Park, just 11 miles away, offering a serene space for wellness and relaxation.

Things to do recommended for groups

Groups visiting Annapolis can enjoy shopping at the Annapolis Mall Shopping Center for a lively experience, catch a captivating performance at The Colonial Players theater, and play a round of golf at the Bay Hills Golf Club, located a short drive away, perfect for outdoor enthusiasts.

*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

If you're planning a trip with a group, family, pets, or are interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide 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 areas for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Annapolis with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with having access to family-friendly amenities like a private swimming pool. Additionally, think about how close you are to attractions that cater to families.
  • Taking your pets with you to Annapolis: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties 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 in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate 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 a private pool in your search criteria as well.

Where to stay in and around Annapolis

Annapolis, Maryland, offers a delightful blend of history and family-friendly activities. Explore the picturesque streets of the historic district, visit the U.S. Naval Academy, and enjoy waterfront dining. Nearby neighborhoods provide a warm, welcoming atmosphere perfect for excursions and relaxation. Take advantage of various housing options, from charming inns to modern hotels, ensuring a comfortable stay while you immerse yourself in the rich culture and vibrant community of Annapolis and its surroundings.

  • Historic District: The Historic District of Annapolis is a charming neighborhood steeped in rich history and culture. Situated around the heart of the city, this area is perfect for families and those looking for a city-themed experience. Visitors can enjoy a blend of education and shopping in its quaint boutiques and vibrant shopping mall centers. Prominent landmarks like the United States Naval Academy and the picturesque dock port offer a glimpse into the city’s maritime heritage. The Historic District's cobblestone streets and colonial architecture make it a delightful place for leisurely strolls and outdoor activities, enhancing your travel experience.
  • Parole: Parole is a lively village located just a short distance from Annapolis. It’s a great destination for families and business travelers alike, featuring a variety of educational institutions and shopping opportunities, including a bustling shopping center. The area's proximity to local landmarks such as the naval academy, scenic beaches, and sports stadiums provide a well-rounded experience for visitors. Whether you’re looking to shop, dine, or engage in recreational activities, Parole offers a city-themed vibe that caters to all interests.
  • Arnold: Located approximately 4 miles from Annapolis, Arnold is an outdoor enthusiast's paradise. Known for its stunning scenery and family-friendly atmosphere, this city offers plenty of recreational options including golf courses and parks. Visitors can explore local attractions like beautiful beaches and serene lakes, as well as the nearby national state park, which showcases Maryland's natural beauty. Whether hiking, picnicking, or simply enjoying the great outdoors, Arnold is a perfect getaway for those seeking a tranquil yet engaging experience.

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 HighAverage
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 SunnyAverageSlightly High
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 simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate significantly. Also, opting for a longer stay can result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental. We're here to help you find the best options for your getaway.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your entire reservation. Being the organizer truly has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and accumulate OneKeyCash on qualifying bookings. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your travel adventures. You can easily start new trips, continue from where you last paused, or manage and view your existing plans. Your saved or booked properties are neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, simply 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)
  • 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)
  • 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:

  • Spa Creek (0.5 mi / 0.8 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)
  • Fort Smallwood Park (11 mi / 17.6 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 when booking a vacation rental?
When planning a vacation rental in Annapolis, Maryland, one of the best areas to consider is the Historic District. This charming neighborhood is known for its well-preserved 18th-century architecture and vibrant atmosphere. Here, you can easily explore top attractions like the Maryland State House, which is the oldest state capitol still in continuous use, and the United States Naval Academy, where you can enjoy guided tours of the beautiful campus. The Historic District has a diverse selection of vacation rentals, with numerous properties available for those seeking a great experience in the heart of the city.

Another excellent choice is Eastport, located just across the bridge from downtown Annapolis. This waterfront neighborhood boasts a laid-back vibe and is famous for its picturesque views of the harbor. Visitors can enjoy the scenic trails along the waterfront and dine at some delightful local restaurants. Eastport also offers easy access to attractions like the Annapolis Maritime Museum, which showcases the area's rich maritime heritage. With a variety of rental options available, this area is great for those looking to enjoy both relaxation and exploration.

Lastly, the West Annapolis area provides a quieter, residential feel while still being conveniently close to the main attractions. This neighborhood is known for its quaint shops and dining options, making it a lovely place to unwind after a day of sightseeing. It's also a short drive or bike ride away from the bustling downtown area, where you can visit the popular City Dock and take in the lively atmosphere. With a good number of vacation rentals in West Annapolis, you'll find a cozy retreat to make your stay enjoyable.
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, Maryland, consider the beautiful areas along the Chesapeake Bay. The Eastport neighborhood, just across the bridge from downtown Annapolis, offers charming waterfront properties with stunning views of the bay and easy access to sandy beaches. Many rentals in this area feature amenities such as private docks, outdoor decks for entertaining, and fully equipped kitchens, superb for families or groups looking to enjoy a seaside getaway.

Another excellent option is the Broadneck Peninsula, where you can find beach houses that provide tranquil settings and proximity to local parks like Sandy Point State Park. Here, visitors can expect spacious outdoor areas, grilling facilities, and family-friendly layouts. Properties often come with access to community amenities like pools and playgrounds, making them ideal for vacationing families.

In addition, the historic district of Annapolis, while not directly on the beach, offers picturesque homes with easy access to the waterfront and nearby sailing activities. Many properties in this area feature historic charm, with modern amenities like gourmet kitchens and cozy living areas, allowing travelers to enjoy both comfort and a taste of local history. Find your rental near the beach in Annapolis.
Are there any houseboat rentals in Annapolis?
In Annapolis, houseboat rentals are available, providing a unique way to experience this charming waterfront city. These rentals can typically be found along the scenic harbor, offering stunning views of the Chesapeake Bay and proximity to popular attractions like the United States Naval Academy and the historic downtown area. Travelers can expect amenities such as cozy living spaces, fully equipped kitchens, and outdoor decks ideal for enjoying the picturesque surroundings.
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 362 available throughout the city. These houses are often located in charming neighborhoods, providing easy access to the historic district, the United States Naval Academy, and the waterfront. Most vacation houses come with amenities such as fully equipped kitchens, spacious living areas, and outdoor patios or decks, great for enjoying the pleasant Maryland weather.

Apartments are also a popular choice, with about 48 options available, typically featuring modern furnishings, kitchen facilities, and convenient access to local shops and restaurants. For those seeking a more quaint experience, about 19 cottages can be found, often located in serene locations, offering a cozy atmosphere with rustic details and outdoor spaces.

Additionally, there are around 12 condos available, which usually provide resort-style amenities like pools and fitness centers. For a great experience, several houseboats are also available, providing a distinctive stay on the water.
Are there any family house rentals in Annapolis?
In Annapolis, Maryland, there are numerous family-friendly house rentals available, with around 298 options to choose from. The charming neighborhoods of Eastport and Murray Hill are particularly appealing for families. Properties in Eastport often feature spacious living areas, fully equipped kitchens, and outdoor patios, making them ideal for gatherings after a day of exploring. This area is conveniently located near the waterfront, where families can enjoy activities such as sailing or visiting the picturesque Annapolis Harbor.

Meanwhile, Murray Hill offers a mix of historic homes and modern amenities, with many properties boasting private yards for kids to play in. Visitors can expect features like comfortable bedrooms, game rooms, and proximity to local parks, such as Broadneck Park, which has playgrounds and sports facilities. See all family-friendly rentals in Annapolis.
Can I rent a vacation home with a pool or hot tub in Annapolis?
In Annapolis, there are several vacation homes available for rent that feature pools and hot tubs, with around 32 options to choose from. This charming city, known for its historic sites and waterfront views, offers properties in various neighborhoods, including the vibrant downtown area and the serene outskirts near Broadneck Park.

Travelers can expect a range of amenities in these rentals, such as private pools, relaxing hot tubs, outdoor entertaining spaces, and fully equipped kitchens, making them ideal for both leisure and family gatherings. 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, with over 200 options available across the city. Many of these homes are situated in charming neighborhoods like Eastport, where visitors can enjoy waterfront views and easy access to local attractions. These rentals typically come equipped with amenities such as outdoor patios, spacious backyards, and modern kitchens, ensuring a comfortable stay for both guests and their pets.

In addition to the vibrant atmosphere of Eastport, the historic downtown area is just a short distance away, offering pet-friendly dining options and shops. The nearby Broadneck Park features walking trails and open spaces, great for exercising pets and enjoying the outdoors. See all pet-friendly rentals in Annapolis.
Are there any remote work vacation rentals in Annapolis?
In Annapolis, there is a wide selection of remote work vacation rentals available, with approximately 413 options for travelers. The city, known for its historic charm and vibrant waterfront, offers properties that cater specifically to those working remotely. Many rentals feature dedicated workspaces, high-speed Wi-Fi, and comfortable office setups, including desks, ergonomic chairs, and laptop workstations, ensuring a productive environment.

Visitors can enjoy the picturesque surroundings, with easy access to local attractions such as the United States Naval Academy and the scenic Annapolis Harbor. Many properties also come equipped with amenities such as fully stocked kitchens, outdoor patios, and cozy living areas, allowing for a balanced experience of 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, popular rental amenities include WiFi, kitchens equipped with essential appliances like coffee and tea makers and blenders, as well as patios for enjoying the pleasant weather. These amenities cater to travelers looking for convenience and comfort, allowing them to prepare meals and relax outdoor after exploring the historic downtown area or visiting the U.S. Naval Academy.
When is the best time to visit Annapolis for a vacation rental?
The best time to visit Annapolis for a vacation rental is during the peak season from May to July, with July being particularly popular among travelers. This time of year brings vibrant energy to the city, as visitors flock to enjoy the picturesque harbor, rich maritime history, and a bustling calendar of events. Expect warm temperatures ranging from the mid-70s to mid-90s Fahrenheit, great for outdoor activities such as sailing, kayaking, and exploring historic sites.

Annapolis truly comes alive in the summer months, especially with the annual events like the Annapolis Arts and Crafts Festival and the Chesapeake Bay Maritime Museum's activities. The pleasant weather and lively atmosphere make it an ideal time for sightseeing and enjoying leisurely strolls through the charming downtown area, filled with boutiques and waterfront dining options.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience with fewer crowds, allowing you to explore the city at a more leisurely pace. The crisp fall air is great for enjoying scenic walks along the waterfront and savoring the last of the autumn colors.

Ultimately, your choice of when to visit Annapolis should align with your preferences for activities and atmosphere.
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?
In Annapolis, visitors can explore a variety of attractions that showcase the city's rich history and maritime charm. The historic district is a must-see, featuring beautifully preserved 18th-century buildings, the Maryland State House, which is the oldest state capitol still in continuous use, and the charming streets lined with boutiques and cafes. Vacation rentals in this area often provide easy access to local landmarks and waterfront views.

The U.S. Naval Academy is another key attraction, where guests can take guided tours to learn about its history and admire the impressive architecture, including the famed chapel. Nearby, the scenic waterfront along the Chesapeake Bay offers opportunities for boating and dining at waterfront restaurants.

For those interested in outdoor activities, Sandy Point State Park is a short drive away, featuring beaches, picnic areas, and trails that provide beautiful views of the bay.
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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