Annapolis featuring street scenes and a city as well as a small group of people

Historic District holiday rentals

We found 192 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 151 homes, 21 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:14 Nov - 21 Nov

Exceptional

(13 reviews)

Secluded Cozy Cottage in Historic Downtown

Annapolis, MD

25% off

AU$625 per night

includes taxes & fees

View of side garden and driveway, with parking for up to 5 cars.

Exceptional

(47 reviews)

Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!

Annapolis, MD

17% off

AU$1,836 per night

includes taxes & fees

Exceptional

(25 reviews)

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

Annapolis, MD

8% off

AU$1,883 per night

includes taxes & fees

Thoughtfully renovated and decorated 3-bedroom, 2.5-bath two blocks from historic West Street. Private driveway with space for up to 3 vehicles.

Exceptional

(5 reviews)

Newly renovated in DTA w parking

Annapolis, MD

8% off

AU$839 per night

includes taxes & fees

Conduit Street Cottage ! Best people watching in town from our porch !

Exceptional

(66 reviews)

Location Location Location!!!50 Steps from Main Street and all of the action

Annapolis, MD

8% off

AU$637 per night

includes taxes & fees

Wonderful

(7 reviews)

Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium

Annapolis, MD

8% off

AU$533 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Historic District

Maryland State House

Find the best place to stay - Historic District

Freshly renovated 3-story home 1 block from USNA!

Sleeps 10 · 3 bedrooms · 2+ bathrooms

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Sleeps 8 · 3 bedrooms · 1+ bathroom

A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!

Sleeps 5 · 2 bedrooms · 1+ bathroom

Relax in the cozy king suite overlooking Historic Downtown Annapolis!

Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!

Sleeps 8 · 4 bedrooms · 3 bathrooms

Top rated rentals - Historic District

Premier Host

Fantastic house - clean, warm & perfectly located to get around Annapolis

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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

What is the most popular type of holiday home accommodation in Historic District?

Houses are the most popular type of holiday home in Historic District, according to our data. Even if you have a different idea about what you want, Stayz has properties in many shapes and sizes. Take a look at our options to find your ideal fit.

How much does it cost to rent a holiday home in Historic District?

Several things affect how much you'll pay for a holiday home in Historic District, like the type of property, length of stay and season. But, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Historic District?

The average price for a holiday home close to the beach in Historic District depends on when you're visiting the area and the style and size of property you're looking for. Find prices easily and quickly on Stayz by entering your preferred travel dates and destination. Then make use of the filter tool to choose the number of bedrooms and amenities that you need, like air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday homes in Historic District?

Yes, there are. You can pick from 118 holiday homes that welcome pets in Historic District on Stayz. Our furry kids need a getaway too, so simply use our search function for pet-friendly holiday homes to book a pad where Spot can join the fun.

What are popular home amenities in Historic District?

Some of the most popular home amenities people prefer in Historic District include an electric car charging station, a nearby waterfront and a nearby river. Whether you're taking a trip with your besties, family or even pets, Stayz holiday homes include the best amenities for starting a new adventure with your loved ones.

Are there large group holiday homes in Historic District?

Choose from 19 holiday properties in Historic District that can host a group of 10 or more people. Whether you're planning time away with the family or a celebration like a birthday, there's ample room to get your group together under the same roof.

Are there holiday homes in Historic District that welcome kids?

With 118 family-friendly holiday properties to pick from in Historic District, there's never been a better time to introduce the kids to the joys of travel. Simply check our "Properties good for families" filter box to view stays packed with conveniences ideal for holidaying families, like multiple bedrooms, backyards, entertainment areas and bunk beds.

What are the top attractions for families in Historic District?

There's a ton of fun things to do and see with the family in Historic District, such as:

Annapolis Maritime Museum
Sandy Point Beach
Annapolis Sailing School

Are there one-bedroom holiday homes in Historic District?

Take your pick from 13 one-bedroom homes in Historic District. Whether you're on the lookout for a cosy cottage or a fancy condo, our one-bedroom properties are great if you don't need a lot of space. One of the perks of having your own place? You won't ever have to share your adventure with strangers.

Can I find two-bedroom holiday homes in Historic District?

Gather your family and enjoy total privacy and comfort in one of the 31 two-bedroom holiday properties Historic District has to offer.

Are there holiday homes with WiFi in Historic District?

Historic District has 51 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to posting pics on social media, these Stayz homes make it a cinch to get online.

How can I find holiday homes with air conditioning in Historic District?

Choose from 115 holiday homes with air conditioning in Historic District giving you that gentle, cool breeze and extra element of comfort. Simply enter your preferred travel dates and then take advantage of our filters to help you locate stays with air conditioning.

How old do you have to be to rent a holiday home in Historic District?

The minimum required age is typically 16, 18 or 21. It can change from property to property on Stayz, so check the rules of your chosen Historic District stay before making a booking.

How long can I rent a holiday home in Historic District for?

The amount of time you can stay in a Historic District holiday home for differs depending on the property. Simply put in your preferred travel dates to see available options that offer extended stays. They come with the things you need to make your extended break more enjoyable such as air conditioning and kitchens. Some Stayz holiday properties may also offer weekly or monthly discounted prices, so you can stay longer for less money.