Historic District Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Where to stay in Historic District

Find the best Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Historic District
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Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

Find hotels in Eastport

Top hotels in Historic District

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,807 reviews)
"The only draw backs were that there is no staff on the property and there was no closet. The rest of the experience was fantastic! Beautiful place, well kept, comfortable, valet parking, great staff at the check in location, best location! In the heat of Annapolis."

Reviewed on 22 Jul, 2025

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Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$321 per night from 17 Aug to 18 Aug
S$321
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (843 reviews)
Nice for a brief stay
"Great location and close to great restaurants. While pet friendly it was difficult to find a doggy potty area. The bathroom had had a leak that was barely patched and the bath had no fan. The parking was valet and we thought our car was parked in an enclosed area but we later saw it in a school parking ..."

Reviewed on 24 Jul, 2025

Annapolis Waterfront Hotel, Autograph Collection
86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

2 out of 5
86 State Cir, Annapolis, MD
The price is S$369 per night from 28 Jul to 29 Jul
S$369
28 Jul - 29 Jul
includes taxes & fees
86 State Circle - Luxury Boutique Hotel
See all 1,268 properties in Historic District
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Historic District holiday package cost?
Cross off another part of the world with our Historic District holiday packages, which start from only . Select the flights and hotels that suit your travel plans. Then, add on a few experiences or tours for an amazing adventure.
How do I get a cheap travel package to Historic District?
You'll save a ton of money if you combine your car rentals, hotels and flights into a Historic District holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1,000,000 properties globally, which means you'll always have plenty of variety to choose from. Like to save even more? Add some exciting activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Historic District?
A trip to Historic District isn't complete until you've seen U.S. Naval Academy and Maryland State House. Stay somewhere close by so you can easily access these fantastic sights.
What are the top hotels in Historic District?
Secure a room at Chic Condo With Balcony In The Heart Of Annapolis. It's one of the neighbourhood's most in-demand properties. Another highly rated option in Historic District is Downtown Annapolis Condo With Free Parking + Coffee.
How far in advance should I book my Historic District holiday?
Be rewarded with the biggest variety at the lowest prices by booking your Historic District holiday nice and early. Airlines usually sell flight tickets around 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Historic District travel package include?
From airfares and hotels to rental cars, Expedia can help you craft a Historic District package that fits you. Heading away for a week or two? Check out a rental car, hotel and flight bundle. If you're taking a short break, a hotel and flight deal could be what you're after. Activities can also be added after you've booked. Our holiday packages make it a cinch to plan and save.
What should I know before booking a Historic District travel package?
Our prices are already low. However, you'll snap up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and loads of choice.
Can I choose my airline with a Historic District Expedia holiday package?
You can. We have more than 550 partner airlines worldwide, so pick the carrier that best fits your needs.
If I'm not able to travel, can I cancel my Historic District holiday package?
Whether it's your flight or hotel, yes, you can cancel or amend it. Booked your Historic District holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may be charged a fee by your hotel, airline or car rental company. For more information, look up our Customer Service Portal. We're here to help you each step of the way.

Things to do

Food Tour Plate

Historic Annapolis Food Tour

S$102
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

S$33
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

S$51
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.