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

Terrace/patio
City Dock
Lounging room, Roku tv
Walking distance to gate 3
Exceptional
(35 reviews)

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

Annapolis

8% off
AU$4,513
for 7 nights, 1 home
AU$645 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
Exterior detail
Marina
Private kitchen
Living area
Exceptional
(22 reviews)

Secluded Cozy Cottage in Historic Downtown

Annapolis

25% off
AU$4,578
for 7 nights, 1 cottage
AU$654 per night
includes taxes & fees
Secluded Cozy Cottage in Historic Downtown
Exterior
Living area
Private kitchen
Living area
Exceptional
(44 reviews)

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Annapolis

8% off
AU$10,849
for 7 nights, 1 home
AU$1,550 per night
includes taxes & fees
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Interior
Private kitchen
Dining
Living area
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

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

Timeless Charm Meets Modern Comfort

Annapolis

7% off
AU$2,975
for 7 nights, 1 home
AU$425 per night
includes taxes & fees
Timeless Charm Meets Modern Comfort
Guest bedroom with queen bed
Renovated kitchen with all major appliances and supplies
Renovated kitchen with all major appliances and supplies
Stylish half-bathroom with heated floors
Exceptional
(21 reviews)

Newly renovated in DTA w parking

Annapolis

7% off
AU$4,072
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Newly renovated in DTA w parking
Enjoy a cup of coffee in the morning or an evening cocktail on the private patio located outside of the kitchen.
Interior
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.
This cozy dining room is a space that invites warmth and togetherness. It is designed to provide a delightful setting for shared meals and cherished moments with friends and family.
Exceptional
(11 reviews)

Charming Charles -Walkable Downtown Annapolis Home

Annapolis

10% off
AU$3,258
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Charming Charles -Walkable Downtown Annapolis Home
Stairs to first floor common area
1st floor kitchen
Exterior detail
Room
Wonderful
(14 reviews)

18th Cent. Charm in Historic Downtown Annapolis

Annapolis

16% off
AU$2,784
for 7 nights, 1 apartment
AU$398 per night
includes taxes & fees
18th Cent. Charm in Historic Downtown Annapolis
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More 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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