Photo by Lori Buchanan

Historic District vacation rentals

We found 183 vacation rentals — enter your dates for availability

Discover a selection of 108 homes, 19 apartments, and other vacation rentals in Historic District that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Historic District

Why visit Historic District

  • Rich History: Explore historic houses and sites that showcase Annapolis's vibrant past.
  • Charming Waterfront: Enjoy scenic views and outdoor activities along the picturesque waterfront.
  • Family-Friendly Activities: Engage in various excursions perfect for families and children.
  • Vibrant Local Culture: Experience the lively downtown with its shops, restaurants, and friendly locals.
  • Diverse Accommodations: Choose from a range of vacation rentals, from cozy cottages to stylish apartments.

Popular types of accommodation around Historic District

Discover the charm of the Historic District with Vrbo's selection of vacation rentals. Whether you're looking for houses, cozy cottages, or stylish apartments, we have options that cater to every traveler. From downtown Annapolis apartments to spacious homes and one-bedroom rentals, you'll find the perfect base to explore the area's rich history and vibrant culture. Choose the ideal accommodation that suits your needs and enjoy a memorable stay in Annapolis.

  • Houses: The top choice for visitors in Historic District, offering spacious and comfortable stays ideal for families, couples, or groups.
  • Cottages: These quaint, charming retreats are the second favorite, perfect for a cozy and picturesque getaway.
  • Apartments: A popular option for those seeking convenience and a home-like atmosphere in the heart of the Historic District.
  • Condos: Offering modern amenities and often great views, these are a favored choice for travelers wanting a stylish stay.
  • House Boats: A unique lodging experience, allowing you to enjoy your vacation on the water in a comfortable setting.**

Top attractions near Historic District

Historic District in Annapolis, Maryland, offers a perfect blend of family-friendly activities and outdoor adventures. Visitors can explore urban parks, marinas, and historic houses, making it an ideal destination for those seeking cultural experiences and quality time with loved ones. Whether you’re enjoying the scenic waterfront or diving into the rich history, there’s something for everyone in this charming area.

  • U.S. Naval Academy: This prestigious institution, located just 0.6 miles from the Historic District, offers a glimpse into naval history with its stunning architecture and beautiful grounds, providing a unique blend of historical and scenic vibes.
  • Chesapeake Bay Bridge: Situated 5 miles away, this iconic modern bridge connects the eastern and western shores and showcases breathtaking views of the bay, embodying a vibrant city atmosphere.
  • Sandy Point State Park: Also 5 miles from the Historic District, this national park invites adventure lovers with its outdoor activities and scenic vistas, perfect for hiking, picnicking, and enjoying nature.

Things to do recommended for couples

For a romantic getaway in Annapolis, enjoy a captivating performance at the Ballet Theater of Maryland, just 0.7 miles from the Historic District. For adventure, try sailing at Annapolis Sailing School, only 1 mile away. Cap your day with a wine tasting at Thanksgiving Farm Wines, 10 miles from the heart of the city.

Things to do recommended for families

Families visiting the Historic District in Annapolis can enjoy the excitement of the Navy-Marine Corps Memorial Stadium, have fun at the Annapolis Bowl arcade, and relax at Fort Smallwood Park, offering a perfect blend of sports, adventure, and wellness experiences for everyone.

Things to do recommended for groups

Explore the Annapolis Mall Shopping Center for a mix of shopping and entertainment, just 3 miles from Historic District. Enjoy a performance at The Colonial Players theater for a cultural experience right in the area. Don't miss the Wild Bird Center, located 2 miles away, for a unique shopping 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 around Historic District

If you're traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to use the appropriate filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Historic District with a group: Think about how many bedrooms you'll require, along with amenities like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these features and much more on Vrbo.
  • Traveling to Historic District with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions is a smart move.
  • Taking your pets with you to Historic District: For many families, a vacation wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Historic District: If you're searching for vacation rentals that offer great deals 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 rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Historic District

Exploring the Historic District of Annapolis, Maryland, is a delightful experience for families and outdoor enthusiasts alike. Stroll through the charming downtown area, where history meets vibrant local culture. Discover the rich heritage of historic downtown Annapolis, enjoy family-friendly excursions, and connect with friendly locals. With its unique blend of history and modernity, the Historic District offers an unforgettable vacation that captures the essence of this beautiful city.

  • Annapolis: Annapolis, the capital of Maryland, is a vibrant city steeped in history and charm. The Historic District is a must-visit, offering a delightful blend of colonial architecture and modern amenities. Travelers can indulge in family-friendly activities, enjoy outdoor experiences along the waterfront, or shop in its bustling shopping centers. Notable attractions include the U.S. Naval Academy, where visitors can learn about naval history, and beautiful nearby beaches and lakes that offer relaxation and recreation. With its picturesque streets and rich heritage, Annapolis provides a unique travel experience that caters to everyone.
  • Murray Hill: Just 0.6 miles from the Historic District, Murray Hill is a quaint neighborhood that combines urban living with a suburban feel. It’s a fantastic spot for families and outdoor enthusiasts, featuring parks and recreational areas that invite exploration and play. The neighborhood offers easy access to educational facilities and local shopping, making it a practical choice for travelers. Nearby attractions include the Naval Academy and beautiful beaches, where visitors can soak up the sun or enjoy water activities. Murray Hill's welcoming atmosphere and proximity to the city make it an ideal place to explore.
  • Naval Academy: The Naval Academy, also located 0.6 miles from the Historic District, is a picturesque village that offers a rich cultural experience. Visitors can immerse themselves in the traditions of the U.S. Navy while enjoying outdoor activities in the surrounding parks and docks. The area is well-suited for families and culture enthusiasts, with educational opportunities and recreational venues nearby. Highlights include the stunning campus of the Naval Academy, the bustling tourist precinct, and the scenic dock port. The Naval Academy's blend of history and community makes it a captivating destination for any traveler.

Best time to go to Historic District

If you're planning a trip to Historic District, 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 a breeze

Are you eager to save on your upcoming vacation? Consider being flexible with your travel dates, as this can lead to lower prices. Additionally, booking a longer stay can often result in substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its advantages. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or view and organize your travel arrangements. You'll see your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Historic District?
In the Historic District of Maryland, vacation houses are the most popular type of rental, with about 140 available in the area. These homes provide ample space and often feature multiple bedrooms, full kitchens, and inviting living areas, making them ideal for families or groups looking to enjoy a comfortable stay while exploring local attractions. Additionally, there are around 19 apartments and several condos and cottages, which offer a more compact alternative for travelers seeking a convenient base close to historic sites and charming streets.
Are there any beach house rentals in Historic District?
In the Historic District of Maryland, there are approximately 173 beach house vacation rentals available, suiting a variety of preferences. These rentals are typically situated near points of interest such as the waterfront, local parks, and historic landmarks, allowing guests to immerse themselves in the area's rich history and vibrant culture. Travelers can expect amenities like spacious living areas, fully equipped kitchens, and outdoor decks or patios great for enjoying the coastal breeze. Many properties also offer features like private gardens, outdoor grilling spaces, and proximity to local attractions, making them ideal for families or groups looking to explore the scenic beauty of the region while enjoying comfortable accommodations.
How much does it cost to rent a vacation home in Historic District?
Prices for vacation rentals in Historic District 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 Historic District 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 Historic District vacation house rentals?
You can find great discounts on house rentals in Historic District 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.
What are popular rental amenities in Historic District?
In the Historic District of Maryland, vacation rentals commonly feature a range of sought-after amenities that enhance the overall visitor experience. Many properties include fully equipped kitchens, allowing travelers to prepare their own meals, alongside coffee and tea makers for a quick morning pick-me-up. Outdoor spaces such as patios or decks are also popular, providing guests with a pleasant area to relax and enjoy the charming surroundings. Additionally, some rentals offer blenders, great for making smoothies or cocktails during a leisurely stay.
Are there any family house rentals in Historic District?
In the Historic District of Maryland, there are numerous family-friendly house rentals available, totaling around 107 options. This charming area is known for its rich history and vibrant atmosphere, making it an excellent choice for family getaways. Many of the homes offer spacious living areas, fully equipped kitchens for preparing meals, and cozy outdoor spaces great for relaxation or play.

Visitors can also enjoy proximity to local attractions such as museums, parks, and waterfront areas, ensuring plenty of activities for all ages.
Can I rent a vacation home with a pool or hot tub in Historic District?
In the Historic District of Maryland, there are several vacation homes available for rent that come with either pools or hot tubs. This charming area is rich in history and offers a unique blend of old-world charm and modern amenities. Travelers can expect properties with features such as private outdoor pools, hot tubs for relaxation, spacious living areas, and fully equipped kitchens, making them superb for families or groups looking for comfort and leisure.
Are there any Historic District vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Historic District 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.
Are there pet-friendly vacation rentals in Historic District?
In the Historic District of Maryland, travelers can find a variety of pet-friendly vacation rentals, with around 81 options available. This area is rich in history and charm, featuring a mix of cozy cottages, charming townhouses, and comfortable apartments. Many of these rentals come with amenities such as fully equipped kitchens, outdoor spaces, and modern conveniences like Wi-Fi and air conditioning, providing an inviting space for both guests and their pets.

The Historic District is also home to several parks and green spaces that are ideal for pet owners. For instance, nearby parks offer walking trails and areas for pets to play, making it easy for travelers to enjoy the outdoors with their furry companions.
Can I find long-stay vacation rentals in Historic District?
A long-stay vacation rental in Historic District 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.
When is the best time to visit Historic District for a vacation rental?
September is the most popular time to visit the Historic District in Maryland, as the summer crowds begin to dwindle, allowing for a more relaxed exploration of this charming area. The peak season spans from July to September, where visitors flock to enjoy the mild weather and vibrant local events. The Historic District offers a delightful mix of outdoor activities, including leisurely strolls along its cobblestone streets, and engaging tours of its fascinating historical sites.

During September, you can expect comfortable temperatures, typically ranging from the low 60s to mid-80s Fahrenheit. This makes it an ideal time for outdoor sightseeing, whether you're wandering through the picturesque gardens or visiting the local museums. The atmosphere is lively yet manageable, superb for those who enjoy a vibrant community without the overwhelming crowds of peak summer months.

For travelers looking for a more budget-friendly option, December presents a wonderful opportunity to experience the Historic District's festive charm. While temperatures may dip to the low 30s to mid-40s Fahrenheit, the holiday decorations and events create a magical ambiance. This quieter time allows for a more intimate experience of the area's history and culture, with fewer tourists around to compete for space at popular attractions.

Ultimately, whether you prefer the bustling energy of September or the tranquil beauty of December, the Historic District has something to offer every type of traveler.
Are there any remote work vacation rentals in Historic District?
In the Historic District of Maryland, there are numerous remote work vacation rentals available, with about 153 options to choose from. This charming area is rich in history and offers a unique blend of cultural attractions and scenic views, making it an ideal location for both work and leisure. Many of the rentals come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs. Some properties may even feature additional conveniences like computer monitors and safes to ensure a productive work environment.

In addition to the work-friendly amenities, staying in the Historic District allows guests to explore local points of interest, such as museums, historical landmarks, and beautiful parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic District vacation rental?
Book your Historic District 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 Historic District?
In the Historic District of Maryland, visitors can explore a variety of attractions that highlight the area's rich history and culture. The charming streets of Annapolis, the state capital, are lined with beautifully preserved 18th-century buildings, including the Maryland State House, which is the oldest state capitol still in continuous legislative use. Close by, the U.S. Naval Academy offers guided tours that provide insight into the nation's military history.

In nearby St. Michaels, guests can enjoy the picturesque waterfront views and visit the Chesapeake Bay Maritime Museum, which showcases the region's maritime heritage. The downtown area is filled with quaint shops and restaurants, superb for a leisurely stroll. Additionally, the historic sites in Easton, such as the Talbot County Courthouse and the Avalon Theatre, provide a glimpse into the past while offering cultural events and performances.

The area surrounding the Historic District also features beautiful parks, like Sandy Point State Park, which offers trails, beaches, and picnic areas, making it ideal for outdoor enthusiasts.
Can I change or cancel my Historic District home rental booking on Vrbo?
To find Historic District 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 Historic District 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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