Annapolis vacation rentals

We found 713 vacation rentals — enter your dates for availability

Select from 383 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:May 22 - May 29

Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Property grounds
9.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

9% off
Price is $1,169
$8,180 for 7 nights
All fees included
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

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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:

  • Bay Hills Golf Club (4.7 mi / 7.6 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Paul Reed Smith Guitars (9.5 mi / 15.4 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)

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:

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