Historic District vacation rentals

We found 186 vacation rentals — enter your dates for availability

Immerse yourself in the timeless charm of Annapolis, where cobblestone streets meander through a vibrant waterfront bustling with sailboats and friendly locals. This historic city invites travelers to explore its rich maritime heritage, from the iconic U.S. Naval Academy to the serene gardens of the William Paca House. With a delightful array of accommodations—cozy cottages, inviting apartments, and spacious homes—your group can enjoy the perfect blend of comfort and convenience, making every moment feel like a cherished getaway.

Holiday rentals with weekly discounts - Historic District

Showing deals for:Nov 27 - Dec 4

Ship's Ladder Stairs to Rooftop Deck
Historic Annapolis and City Dock
Rear Entry and Rooftop Balcony
Quaint Pinkney Street
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

13% off
$384
$2,687 for 7 nights
All fees included
Historic Downtown Charmer, Water Views and Parking!
The master bedroom boasts of natural light, en-suite bathroom and ample closet space.
Property grounds
This open kitchen allows you the ability to cook meals or just sit around the spacious dining table that accommodates up to 8 people.
Complemented by earthy tones and natural materials such as wooden floors, this space provides a place to relax, watch TV or even host a game night.
Exceptional
(16 reviews)

Downtown Pinkney House w/Parking

Annapolis

8% off
$416
$2,910 for 7 nights
All fees included
Downtown Pinkney House w/Parking
Walking distance to gate 3
City Dock
Terrace/patio
Kitchen/lounging/dining room
Exceptional
(34 reviews)

Gem in Downtown Annapolis, close to USNA, St. John's College

Annapolis

8% off
$417
$2,920 for 7 nights
All fees included
Gem in Downtown Annapolis, close to USNA, St. John's College
Dining room with space for 6
Updated kitchen with all major appliances
Comfortable and cozy living room with fireplace (for aesthetic only), Smart TV, comfortable seating, games/puzzles, and books.
Comfortable and cozy living room with fireplace (for aesthetic only), Smart TV, comfortable seating, games/puzzles, and books.
Exceptional
(8 reviews)

Timeless Charm Meets Modern Comfort

Annapolis

8% off
$314
$2,199 for 7 nights
All fees included
Timeless Charm Meets Modern Comfort
Second level with two bedrooms, one full bath, and an office area
Bright and updated kitchen
Cozy family room with a queen sofa bed and room-darkening curtains
Primary bedroom with king bed and cathedral ceiling
Exceptional
(14 reviews)

Naval Academy Gate 1

Annapolis

8% off
$275
$1,926 for 7 nights
All fees included
Naval Academy Gate 1
Private kitchen
Property grounds
Less than 1/2 mile to the newly rebuilt Annapolis Yacht Club
Dining table seats 6 comfortable, 8 if you want to get friendly!
Exceptional
(76 reviews)

Beautifully Renovated Historic District Home

Annapolis

11% off
$569
$3,986 for 7 nights
All fees included
Beautifully Renovated Historic District Home
Clawfoot tub
1st floor kitchen
Front of home. Apt door located under front stoop
King bed. Luxury linens, vast pillow options & wonderfully comfortable mattress
Wonderful
(14 reviews)

18th Cent. Charm in Historic Downtown Annapolis

Annapolis

17% off
$246
$1,721 for 7 nights
All fees included
18th Cent. Charm in Historic Downtown Annapolis
The updated kitchen features sleek, stainless tell appliances that bring a modern touch to the space. The kitchen offers a convenient and stylish environment for your culinary endeavors.
Interior
Complemented by earthy tones and natural materials such as wooden floors and exposed brick, this space exudes a sense of tranquility.
Enjoy a cup of coffee in the morning or an evening cocktail on the private patio located outside of the kitchen.
Exceptional
(10 reviews)

Charming Charles -Walkable Downtown Annapolis Home

Annapolis

12% off
$319
$2,233 for 7 nights
All fees included
Charming Charles -Walkable Downtown Annapolis Home

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Find out more about Historic District

Why visit Historic District

  • Rich history: Explore historic properties and learn about Annapolis' maritime heritage.
  • Scenic waterfront: Stroll along the picturesque Annapolis Harbor and enjoy beautiful views.
  • Charming boutiques and cafes: Discover delightful shops and eateries nestled in the downtown area.
  • Family-friendly activities: Enjoy a variety of engaging experiences suitable for all ages.
  • Welcoming atmosphere: Experience the warmth of friendly locals as you explore this iconic destination.

Popular types of accommodation around Historic District

If you’re looking for a memorable stay in Historic District, you’ll be pleased to discover a variety of popular accommodations. From charming houses and cozy cottages to stylish apartments, there’s something for everyone. Whether you’re considering Annapolis hotels, an inviting Annapolis inn, or an elegant waterfront hotel, our vacation rentals offer the perfect blend of comfort and convenience to enhance your travel experience.

  • Houses: These are the top choice for travelers looking for spacious and comfortable accommodations in Historic District, perfect for families or groups.
  • Cottages: Quaint and charming, cottages offer a cozy retreat for those wanting a unique experience in the heart of Historic District.
  • Apartments: Ideal for solo travelers or couples, apartments provide a convenient and versatile option with all the essential amenities.
  • Condos: Featuring modern designs, condos are popular for their stylish living spaces and access to community amenities.
  • House Boats: For a memorable stay, consider house boats, which offer a unique waterfront experience in Historic District.**

Top attractions in Historic District

Historic District in Annapolis, Maryland, offers a delightful blend of family-friendly activities and outdoor adventures. Visitors can explore historic properties, stroll along the Annapolis waterfront, and enjoy the scenic Annapolis Harbor. With its charming urban parks and rich cultural experiences, the Historic District is perfect for those seeking to immerse themselves in the city's history and vibrant atmosphere. A day in Annapolis promises memorable experiences for travelers of all ages.

  • Annapolis City Dock: A picturesque waterfront area, Annapolis City Dock offers a blend of historical charm and scenic views. Enjoy watching boats sail in and out while exploring local shops and eateries nearby.
  • Maryland State House: As the oldest state capitol still in continuous use, the Maryland State House is rich in history and culture. Visitors can admire its stunning architecture and learn about Maryland's legislative history.
  • William Paca House: This beautifully restored 18th-century home showcases the life of signer William Paca. Explore its lush gardens and historic rooms, immersing yourself in colonial culture.

Things to do recommended for couples

For a romantic getaway in Annapolis, consider a visit to the Old South Country Club, located 14 miles from the Historic District. This private club offers a luxurious atmosphere perfect for couples looking to unwind and enjoy each other's company amidst beautiful surroundings.

Things to do recommended for families

Families will love exploring the U.S. Naval Academy, where they can learn about naval history. A stroll along the scenic waterfront is perfect for enjoying local shops and eateries. Don't miss the historic Maryland State House, the oldest state capitol still in continuous use.

Things to do recommended for groups

Groups visiting Historic District in Annapolis can enjoy a guided walking tour of the charming waterfront, explore the Maryland State House, and savor fresh seafood at local restaurants. Don't miss a boat tour of the Chesapeake Bay for a unique perspective of this historic area.

*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, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Historic District with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Historic District with young kids: Traveling with young kids can be quite demanding. It's essential to prioritize their comfort and safety, along with ensuring that there are suitable amenities available, 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 Historic District: For many families, a vacation isn't truly satisfying without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most 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 in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Historic District

Explore the enchanting Historic District of Annapolis, where family-friendly vibes meet rich history. Stroll through downtown Annapolis to discover charming boutiques and delightful cafes, all steeped in the city's maritime heritage. Don’t miss the chance to experience the warm atmosphere and friendly locals as you uncover the secrets of this iconic destination. From historical excursions to scenic waterfront views, Annapolis promises a vacation filled with charm and unforgettable memories.

  • Annapolis: As the vibrant capital of Maryland, Annapolis is a city rich in history and maritime charm. The Historic District, where cobblestone streets meet stunning waterfront views, offers visitors an array of family-friendly activities and outdoor experiences. Popular attractions include the U.S. Naval Academy, where you can explore its impressive grounds, and the scenic Chesapeake Bay, perfect for leisurely walks or picnics. Shopping enthusiasts will enjoy the unique boutiques and local shops scattered throughout the district, making it a delightful blend of education, leisure, and historic exploration.
  • Naval Academy: Located a mere 0.6 miles from the Historic District, the Naval Academy is a picturesque village brimming with cultural and outdoor experiences. Visitors can immerse themselves in the history of naval education and military traditions while enjoying the beautiful campus. The Academy also features various educational opportunities, as well as shopping areas that cater to tourists. Highlights include the sports facilities and stadium, where you can catch exciting events, and the nearby bay, which offers stunning views and opportunities for water-based activities.
  • Murray Hill: Just 0.6 miles from the Historic District, Murray Hill is a charming neighborhood known for its scenic beauty and family-friendly atmosphere. This area is ideal for outdoor enthusiasts, with parks and green spaces perfect for picnics and leisurely strolls. Visitors can explore local shops and a shopping mall center, making it convenient for a day out. Key attractions include the nearby U.S. Naval Academy and the picturesque bay, providing a blend of educational and recreational activities within a tranquil setting.

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 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 eager to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you may find impressive savings by opting for an extended stay. 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.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved or booked, all organized under Potential, Upcoming, or Current Trips. To start using 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 93 available throughout the area. These houses often come equipped with multiple bedrooms, spacious living areas, and outdoor spaces such as gardens or patios, making them ideal for families or groups looking to enjoy the local charm. Additionally, there are around 17 apartments available, which provide a more compact option for travelers, typically featuring fully equipped kitchens and cozy living spaces. For those seeking a great experience, several condos and cottages are also offered, providing various amenities to enhance the stay.
Are there any beach house rentals in Historic District?
In the Historic District of Maryland, there are approximately 47 beach house rentals available. These properties are typically situated in charming neighborhoods that reflect the area's rich history and coastal charm. Travelers can expect a variety of amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios that allow for relaxing evenings while enjoying the coastal breeze. Many of these beach houses also feature multiple bedrooms, making them ideal for families or groups seeking a comfortable and inviting atmosphere.
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 amenities that enhance the guest experience. Many properties include fully equipped kitchens, allowing travelers to prepare their own meals and enjoy the convenience of home cooking. Decks or patios are also prevalent, providing outdoor spaces for relaxation and enjoyment of the scenic surroundings. Additionally, several rentals come equipped with coffee and tea makers for those who appreciate a warm beverage at any time. Guests can expect thoughtful touches like paper towels for convenience, making stays more comfortable.
Can I find family house rentals in Historic District?
In the Historic District of Maryland, there is a substantial selection of family-friendly homes, with around 65 options available. This charming area is known for its rich history and picturesque scenery, making it an appealing destination for families. Many of these properties offer spacious living areas, fully equipped kitchens, and outdoor spaces great for children to play or for family gatherings.Travelers can expect amenities such as Wi-Fi, air conditioning, and sometimes even backyard barbecues, ensuring a comfortable stay. Furthermore, the Historic District is close to significant landmarks and attractions, including museums, parks, and waterfront areas, providing ample opportunities for exploration and entertainment.
Can I rent a vacation home with a pool or hot tub in Historic District?
In the Historic District of Maryland, travelers will find several vacation homes available for rent that feature both pools and hot tubs. This charming area, rich in history and character, offers a variety of properties that cater to those seeking relaxation and leisure. Many of these rentals come equipped with private pools, inviting hot tubs, outdoor living spaces, and fully stocked kitchens, making them ideal for families or groups looking to unwind after a day of exploring the local attractions.
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.
Can I book pet-friendly vacation rentals in Historic District?
In the Historic District of Maryland, travelers will find an impressive selection of pet-friendly vacation rentals, with about 39 options available. The area is known for its charming streets and rich history, making it a delightful place for both visitors and their furry companions. Many of the vacation rentals here come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.The Historic District is also in proximity to several parks and pet-friendly attractions, allowing for enjoyable walks and exploration. Nearby parks often feature walking trails and open spaces, great for exercising pets and enjoying the scenic beauty of the area.
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 best time to book a vacation rental in the Historic District of Maryland, as the summer crowds begin to dwindle while the weather remains pleasantly warm. This transitional month offers a unique blend of outdoor activities and historical exploration, making it ideal for travelers seeking both adventure and relaxation.The peak season runs from July to September, drawing visitors eager to enjoy the vibrant local culture and various events. During this time, you can explore the charming streets lined with historical architecture and partake in outdoor festivals that celebrate the area's rich heritage. The mild temperatures in September, typically ranging from the low 60s to mid-70s Fahrenheit, create a comfortable environment for sightseeing and leisurely strolls.For those looking for a more budget-friendly option, December can be an excellent time to visit, as the Historic District transforms into a winter wonderland adorned with festive decorations. Although it's considered low season, the holiday spirit offers a unique charm, with opportunities for cozy gatherings and local holiday events.Ultimately, your choice of when to visit the Historic District should reflect your preference for bustling summer activities or the peaceful ambiance of the fall and winter months.
Are there any remote work vacation rentals in Historic District?
In the Historic District of Maryland, there are numerous remote work vacation rentals available, totaling around 110 options. This area, rich in history and charm, provides a conducive environment for remote work. Travelers can expect properties equipped with essential amenities such as free Wi-Fi, dedicated desks, and comfortable chairs, allowing for a productive work-from-home experience. Many rentals also offer additional conveniences like reliable internet access, ensuring that you stay connected throughout your stay.The Historic District features beautiful architecture and is close to various points of interest, including museums, local shops, and scenic parks. After a day of work, guests can explore the area's rich cultural offerings or enjoy a leisurely stroll through its picturesque streets. 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, Maryland, United States of America?
In the Historic District of Maryland, visitors can experience firsthand a rich tapestry of attractions. The area is renowned for its beautifully preserved 18th and 19th-century architecture, particularly along streets like High Street, where historical homes and buildings are open for tours. The Historic District is home to the Maryland State House, the oldest state capitol still in continuous legislative use, which offers guided tours that delve into the state's history.Nearby, the waterfront area along the Annapolis Harbor provides stunning views and is a great spot for leisurely walks or dining at local seafood restaurants. The United States Naval Academy, located just a short walk from the Historic District, offers a fascinating glimpse into military history and features an impressive chapel and museum.For those interested in arts and culture, the district hosts various galleries and theaters, particularly around West Street, where visitors can enjoy local performances and exhibitions.
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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