Historic District holiday lettings

We found 179 holiday rentals — enter your dates for availability

Discover a selection of 108 homes, 17 apartments and other holiday rentals in Historic District that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a garden and pool. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Why visit Historic District

  • Rich history: Explore the Annapolis National Historic Landmark District, showcasing significant historical sites and stunning architecture.
  • Charming streets: Stroll through picturesque streets lined with independent shops and delightful eateries, perfect for a leisurely day out.
  • Outdoor adventures: Enjoy urban parks and the marina, offering various activities for families and nature lovers alike.
  • Walking tours: Discover the area’s heritage through engaging walking tours that highlight its fascinating past.
  • Comfortable accommodation: Choose from charming private homes, cottages, and stylish apartments for a memorable stay.

Popular types of accommodation around Historic District

If you’re pondering the types of accommodation available in the Historic District, worry not—we’ve got you sorted. Our most sought-after options include charming Houses, delightful Cottages, and stylish Apartments. Enjoy the area’s beautiful architecture while benefiting from convenient amenities, all within close proximity to local gems like the Westin Annapolis, Maryland Inn, and Holland House. Experience the perfect blend of comfort and character during your stay.

  • Houses: The top choice for accommodation in the Historic District, offering spacious and comfortable stays ideal for families or groups.
  • Cottages: A charming option, these quaint retreats provide a cosy atmosphere perfect for a romantic getaway or peaceful escape.
  • Apartments: Conveniently located, these self-catering options offer flexibility and are suited for both short and extended stays.
  • Condos: Modern and often featuring amenities, condos are a popular choice for those seeking a blend of comfort and convenience.
  • Villas: Luxurious and spacious, villas provide an upscale experience for travellers looking for a more indulgent stay.**

Top attractions near Historic District

The Historic District of Annapolis is perfect for family outings and outdoor adventures, offering a blend of culture and history. Explore the Annapolis National Historic Landmark District, enjoy walking tours, and visit the historic houses around the charming Annapolis Harbour. With its urban parks and marina, there's something for everyone to experience and enjoy in this captivating area.

  • U.S. Naval Academy: A prestigious military academy steeped in history, showcasing impressive architecture and scenic grounds. Visitors can explore its rich naval heritage and even attend a fascinating guided tour.
  • Chesapeake Bay Bridge: An engineering marvel, this modern bridge offers stunning views of the bay and the city skyline. It's a fantastic spot for photographs and a unique perspective on the area's coastal beauty.
  • Sandy Point State Park: A beautiful national park perfect for outdoor adventures, featuring sandy beaches, hiking trails, and picnic areas. Ideal for nature lovers seeking a bit of excitement and relaxation.

Things to do recommended for couples

For a romantic getaway in Annapolis, consider sailing at the Annapolis Sailing School for an adventurous day on the water. Enjoy a captivating performance at the Ballet Theater of Maryland, or indulge in delightful wines at Thanksgiving Farm Wines, perfect for a couple's retreat.

Things to do recommended for families

Families will enjoy the vibrant atmosphere at the Navy-Marine Corps Memorial Stadium, located 497m from the Historic District. For some adventure, visit the Annapolis Bowl, 1.9km away, or unwind at Fort Smallwood Park, 6.8km away, offering relaxation and wellness.

Things to do recommended for groups

Explore the vibrant Westfield Annapolis Mall for shopping and entertainment, only 1.9km from the Historic District. Enjoy a performance at The Colonial Players theatre, right in the heart of the area, or visit the Wild Bird Center, located 1.2km away, for a unique experience.

What do I need to keep in mind when booking a vacation around Historic District

If you’re travelling with a group, family, or pets, or if you’re considering longer stays, be sure to set your filters according to your key priorities. 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, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Historic District with young kids: Taking a trip with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Historic District: For many families, a holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Historic District: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Historic District

Exploring the Historic District of Annapolis, Maryland, offers a delightful blend of family-friendly activities and rich heritage. Stroll through the charming streets of downtown Annapolis, where independent shops and eateries abound. Immerse yourself in the local history at iconic sites within the Annapolis Historic District. With its welcoming atmosphere and picturesque surroundings, this destination is perfect for outdoor adventures, leisurely excursions, and creating lasting memories with loved ones.

  • Annapolis: Annapolis is a vibrant city located a mere 50m from the Historic District, making it an ideal starting point for your exploration. Known for its family-friendly atmosphere and outdoor activities, visitors can enjoy a range of experiences, from educational tours to leisurely shopping at local malls and centres. Notable attractions include the Naval Academy, scenic beaches, and picturesque lakes that invite outdoor recreation and relaxation.
  • Murray Hill: Situated 373m from the Historic District, Murray Hill is a charming neighbourhood perfect for families and outdoor enthusiasts. This area features a delightful mix of educational venues, shopping areas, and recreational spaces. Visitors can explore its inviting parks and green spaces while enjoying proximity to the Naval Academy and nearby beaches. Murray Hill offers a tranquil urban retreat, ideal for leisurely strolls and family outings.
  • Naval Academy: The Naval Academy, located 373m from the Historic District, is a unique village that embodies culture and history. This area attracts families and outdoor lovers alike with its rich educational offerings and engaging shopping options. Key attractions include the stunning academy grounds, a bustling tourist precinct, and the scenic dock port, where visitors can take in the maritime charm and learn about the naval traditions that shape this iconic location.

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 hoping to cut costs on your upcoming holiday? It’s worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often allows for substantial savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your existing arrangements, or manage your bookings with ease. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips for your convenience. To delve into Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Historic District?
In the Historic District of Maryland, holiday houses are the most prevalent type of rental, with around 138 available across the charming area. These houses often feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor spaces, making them ideal for families or larger groups. Additionally, there are approximately 18 apartments available, which provide a more compact living arrangement with similar amenities, superb for couples or solo travellers. A few condos and cottages can also be found, offering unique stays that blend comfort with local character.
Are there any beach house rentals in Historic District?
In the Historic District of Maryland, there are around 46 beach house rentals available, offering a charming escape for travellers. These rentals typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas, superb for families or groups looking to enjoy a seaside holiday. Many properties also include outdoor spaces such as decks or patios, allowing guests to relax and take in the coastal breeze.
How much does it cost to rent a holiday home in Historic District?
Prices for holiday 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 holiday 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.
Are there any Historic District holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Historic District with parking available—perfect for families or travellers 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 find long-stay holiday rentals in Historic District?
A long-stay holiday rental in Historic District is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Historic District for a holiday rental?
September is the most popular time to visit the Historic District in Maryland, as the summer crowds begin to dwindle and the weather remains pleasantly warm. The peak season runs from July to September, when visitors flock to enjoy the charming streets, historic landmarks, and vibrant local culture. This period also features delightful outdoor festivals and events that celebrate the area's rich heritage, making it an ideal time for those keen to immerse themselves in the local scene.

During September, temperatures are generally mild, typically ranging from the mid-teens to low 20s Celsius. This makes it comfortable for outdoor activities such as leisurely strolls through the picturesque streets, guided tours of historical sites, or picnics in the parks. Additionally, the stunning autumn foliage begins to emerge, enhancing the district's already picturesque scenery.

For those who are looking for a more budget-friendly option, December offers a great experience with lower rental rates. While the weather is cooler, the Historic District transforms into a charming winter wonderland, complete with festive decorations and holiday events. This quieter month allows visitors to enjoy the tranquillity of the area, explore local shops, and perhaps find some great deals on holiday gifts.
Are there any remote work holiday rentals in Historic District?
In the Historic District of Maryland, there are ample remote work holiday rentals available, with around 155 options to choose from. This picturesque area, rich in history and culture, provides an ideal backdrop for those looking to balance work and leisure. Many of these properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desks, and comfortable office chairs. Some accommodations even feature additional conveniences such as computer monitors and safes, ensuring a productive and secure working environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Historic District holiday rental?
Book your Historic District holiday 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 holiday 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 take part in a rich tapestry of attractions. The area is renowned for its well-preserved 18th and 19th-century architecture, particularly along streets like Church Circle and State Circle, where the Maryland State House stands as a prominent feature. Nearby, the William Paca House and Garden offers a glimpse into historic life with its beautifully landscaped grounds and historic interiors.

For those interested in maritime history, the Annapolis Maritime Museum provides insights into the area's nautical past, while the bustling City Dock is superb for leisurely strolls, dining, and enjoying the waterfront views. The vibrant arts scene can also be explored through local galleries and theatres, particularly on West Street, where numerous shops and eateries contribute to the charming atmosphere.
Can I change or cancel my Historic District home rental booking on Vrbo?
To find Historic District holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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