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Historic District holiday rentals

We found 189 holiday rentals — enter your dates for availability

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September 2025

October 2025

Discover a selection of 115 homes, 16 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:26 Dec - 2 Jan

In ground saltwater heated pool + hot tub!

Exceptional

(23 reviews)

USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!

Annapolis, MD

8% off

for 7 nights, 1 home

AU$2,576 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

(8 reviews)

Newly renovated in DTA w parking

Annapolis, MD

8% off

for 7 nights, 1 home

AU$1,023 per night

includes taxes & fees

Exceptional

(28 reviews)

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

Annapolis, MD

8% off

for 7 nights, 1 home

AU$1,861 per night

includes taxes & fees

Relax in the cozy king suite overlooking Historic Downtown Annapolis!

Exceptional

(37 reviews)

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

Annapolis, MD

8% off

for 7 nights, 1 home

AU$1,132 per night

includes taxes & fees

Exceptional

(14 reviews)

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Annapolis, MD

8% off

for 7 nights, 1 home

AU$2,685 per night

includes taxes & fees

spacious and comfortable living room, with table/six chairs at far end

Exceptional

(24 reviews)

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, MD

7% off

for 7 nights, 1 home

AU$3,077 per night

includes taxes & fees

Exceptional

(27 reviews)

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

Annapolis, MD

8% off

for 7 nights, 1 home

AU$696 per night

includes taxes & fees

Stately Historic Colonial in the heart of Downtown Annapolis

Exceptional

(107 reviews)

One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !

Annapolis, MD

8% off

for 7 nights, 1 home

AU$857 per night

includes taxes & fees

Beautiful eat-in kitchen - table that expands from seating for four to eight

Exceptional

(15 reviews)

Beautiful Blend of Restoration and Renovation in this Downtown Home

Annapolis, MD

20% off

for 7 nights, 1 home

AU$1,245 per night

includes taxes & fees

Exceptional

(8 reviews)

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

Annapolis, MD

8% off

for 7 nights, 1 home

AU$536 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

7% off

for 7 nights, 1 home

AU$631 per night

includes taxes & fees

Exceptional

(284 reviews)

Annapolis Condominium in the heart of the historic center

Annapolis, MD

20% off

for 7 nights, 1 apartment

AU$504 per night

includes taxes & fees

Exceptional

(10 reviews)

Charming 239-year-old former tavern 1 block to water & shops

Annapolis, MD

8% off

for 7 nights, 1 home

AU$1,298 per night

includes taxes & fees

Exceptional

(31 reviews)

Pristine Downtown 1-Bedroom Steps from State House

Annapolis, MD

8% off

for 7 nights, 1 apartment

AU$393 per night

includes taxes & fees

Larger of the 2 bedrooms, with a queen bed and sitting area

Exceptional

(24 reviews)

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Annapolis, MD

12% off

for 7 nights, 1 apartment

AU$469 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

Premier Host

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

Sleeps 8 · 3 bedrooms · 1+ bathroom

Cool 1870's home anchored in the Historic District with modern amenities.

Sleeps 10 · 5 bedrooms · 3 bathrooms

Premier Host

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

Sleeps 5 · 2 bedrooms · 1+ bathroom

Premier Host

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Sleeps 16 · 6 bedrooms · 4+ bathrooms

Top rated rentals - Historic District

Premier Host

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

Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!

Simon M.

Stayed Dec 2017

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

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.