Historic District holiday homes

We found 190 holiday rentals — enter your dates for availability

Discover a selection of 154 homes, 18 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:22 Aug - 29 Aug

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

Exterior
10 out of 10 rating
Exceptional
(7 reviews)

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

Annapolis, MD

8% off
Price is NZ$17,220
NZ$2,460 per night
includes taxes & fees
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

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

Exterior
10 out of 10 rating
Exceptional
(9 reviews)

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

Annapolis, MD

8% off
Price is NZ$9,961
NZ$1,423 per night
includes taxes & fees
Charming 239-year-old former tavern 1 block to water & shops

Image gallery for All-stop. Rental Midships.

Exterior
10 out of 10 rating
Exceptional
(25 reviews)

All-stop. Rental Midships.

Annapolis, MD

8% off
Price is NZ$6,992
NZ$999 per night
includes taxes & fees
All-stop. Rental Midships.

Image gallery for Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Front of the house, facing quiet and charming Prince George Street
10 out of 10 rating
Exceptional
(22 reviews)

Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Annapolis, MD

16% off
Price is NZ$5,627
NZ$804 per night
includes taxes & fees
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Find spaces that suit your style

  • 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, Bookabach 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 Bookabach 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 Bookabach. 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, Bookabach 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 Bookabach 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 Bookabach, 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 Bookabach holiday properties may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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