Historic District holiday rentals

We found 186 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:27 Nov - 4 Dec

Rear Entry and Rooftop Balcony
Historic Annapolis and City Dock
Quaint Pinkney Street
Living Room with Cable Television
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,190
for 7 nights, 1 home
AU$599 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Complemented by earthy tones and natural materials such as wooden floors, this space provides a place to relax, watch TV or even host a game night.
Property grounds
The master bedroom boasts of natural light, en-suite bathroom and ample closet space.
This open kitchen allows you the ability to cook meals or just sit around the spacious dining table that accommodates up to 8 people.
Exceptional
(16 reviews)

Downtown Pinkney House w/Parking

Annapolis

7% off
AU$4,576
for 7 nights, 1 home
AU$654 per night
includes taxes & fees
Downtown Pinkney House w/Parking
Kitchen/lounging/dining room
City Dock
Walking distance to gate 3
Lounging room, Roku tv
Exceptional
(34 reviews)

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

Annapolis

8% off
AU$4,592
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Gem in Downtown Annapolis, close to USNA, St. John's College
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.
Private, fenced outdoor space
Exceptional
(8 reviews)

Timeless Charm Meets Modern Comfort

Annapolis

7% off
AU$3,488
for 7 nights, 1 home
AU$498 per night
includes taxes & fees
Timeless Charm Meets Modern Comfort
King bed. Luxury linens, vast pillow options & wonderfully comfortable mattress
1st floor kitchen
Exterior detail
Front of home. Apt door located under front stoop
Wonderful
(14 reviews)

18th Cent. Charm in Historic Downtown Annapolis

Annapolis

16% off
AU$2,726
for 7 nights, 1 apartment
AU$389 per night
includes taxes & fees
18th Cent. Charm in Historic Downtown Annapolis
Waterfront park one block away
Property grounds
Dining table seats 6 comfortable, 8 if you want to get friendly!
Less than 1/2 mile to the newly rebuilt Annapolis Yacht Club
Exceptional
(76 reviews)

Beautifully Renovated Historic District Home

Annapolis

10% off
AU$6,276
for 7 nights, 1 home
AU$897 per night
includes taxes & fees
Beautifully Renovated Historic District Home
Second level with two bedrooms, one full bath, and an office area
Bright and updated kitchen
Primary bedroom with king bed and cathedral ceiling
Bright and updated kitchen
Exceptional
(14 reviews)

Naval Academy Gate 1

Annapolis

7% off
AU$3,002
for 7 nights, 1 home
AU$429 per night
includes taxes & fees
Naval Academy Gate 1
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.
Interior
Enjoy a cup of coffee in the morning or an evening cocktail on the private patio located outside of the kitchen.
Complemented by earthy tones and natural materials such as wooden floors and exposed brick, this space exudes a sense of tranquility.
Exceptional
(10 reviews)

Charming Charles -Walkable Downtown Annapolis Home

Annapolis

11% off
AU$3,521
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
Charming Charles -Walkable Downtown Annapolis Home

  • 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.

More holiday ideas