Historic District holiday rentals
We found 181 holiday rentals — enter your dates for availability
Discover a selection of 114 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.
Holiday rentals with weekly discounts – Historic District
Showing deals for:8 Jan - 15 Jan

Exceptional
(35 reviews)
Gem in Downtown Annapolis, close to USNA, St. John's College
Annapolis
AU$4,513
for 7 nights, 1 home
AU$645 per night
includes taxes & fees

Exceptional
(22 reviews)
Secluded Cozy Cottage in Historic Downtown
Annapolis
AU$4,578
for 7 nights, 1 cottage
AU$654 per night
includes taxes & fees

Exceptional
(44 reviews)
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Annapolis
AU$10,849
for 7 nights, 1 home
AU$1,550 per night
includes taxes & fees

Exceptional
(7 reviews)
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Annapolis
AU$6,014
for 7 nights, 1 home
AU$859 per night
includes taxes & fees

Exceptional
(9 reviews)
Timeless Charm Meets Modern Comfort
Annapolis
AU$2,975
for 7 nights, 1 home
AU$425 per night
includes taxes & fees

Exceptional
(21 reviews)
Newly renovated in DTA w parking
Annapolis
AU$4,072
for 7 nights, 1 home
AU$582 per night
includes taxes & fees

Exceptional
(11 reviews)
Charming Charles -Walkable Downtown Annapolis Home
Annapolis
AU$3,258
for 7 nights, 1 home
AU$465 per night
includes taxes & fees

Wonderful
(14 reviews)
18th Cent. Charm in Historic Downtown Annapolis
Annapolis
AU$2,784
for 7 nights, 1 apartment
AU$398 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Historic District

Thurgood Marshall Memorial
More information about Thurgood Marshall Memorial. Opens in a new window.Find the best place to stay - Historic District

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital
Sleeps 10 · 5 bedrooms · 1 bathroom

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Sleeps 16 · 6 bedrooms · 4+ bathrooms

Secluded Cozy Cottage in Historic Downtown
Sleeps 8 · 2 bedrooms · 1 bathroom

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Sleeps 5 · 2 bedrooms · 1+ bathroom

Charming garden row home, easy 4 block walk to the heart of Annapolis.
Sleeps 6 · 3 bedrooms · 1+ bathroom

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Sleeps 8 · 3 bedrooms · 1+ bathroom
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
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 thin and the weather remains pleasantly warm. This period falls within the peak season, which spans from July to September, attracting visitors eager to immerse themselves in the area's rich history and vibrant culture. With comfortable temperatures ranging from about 15 to 25 degrees Celsius, it's an ideal time for outdoor activities, leisurely strolls through historic streets, and enjoying the local festivals that often take place during this month.As the summer heat wanes, September offers a delightful atmosphere for sightseeing, allowing you to explore landmarks such as the charming waterfront and beautifully preserved historic architecture without the hustle and bustle of peak tourist activity. The area is particularly inviting for those who appreciate a blend of convenience and quality in their travel experiences.For those looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it presents unique opportunities to experience the Historic District adorned in festive decorations, providing a magical ambiance that's superb for winter strolls and cozy gatherings.
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 well-preserved historic architecture and vibrant history. One of the highlights is the Historic District itself, which features charming streets lined with 18th and 19th-century buildings, offering a glimpse into the past.Nearby, the Maryland State House, the oldest state capitol still in continuous legislative use, is a must-visit for its stunning architecture and historical significance. The area is also home to the United States Naval Academy, where guests can take guided tours to learn about naval history and admire the beautiful campus.For those interested in the arts, the Banneker-Douglass Museum showcases African American heritage and history in Maryland, while the nearby William Paca House and Garden provides a serene escape with its beautifully landscaped gardens and guided tours of the historic home.Additionally, the waterfront area along the Annapolis Harbour offers picturesque views and a variety of dining options, making it a lovely spot for a leisurely stroll or a meal with a view.
Are all fees included in the Historic District holiday homes prices shown on Stayz?
Stayz 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.
Are there any Historic District holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 any discounts for Historic District holiday homes?
You can find great discounts on holiday homes in Historic District on Stayz, 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.
Can I change or cancel my Historic District holiday home booking on Stayz?
To find Historic District holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Historic District?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Historic District holiday home?
Book your Historic District holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Historic District?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Historic District to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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