Annapolis Holidays

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Your Annapolis Holiday

Organising your next big escape is easy with an Annapolis holiday package. The neighbourhood of Historic District, which is good for history, makes a good starting point to discover the wonders of this unique city. Any trip to Annapolis needs a well-planned itinerary. Fill yours with major attractions such as U.S. Naval Academy, Maryland State House and William Paca House. A couple of quick clicks is all it takes to build the perfect Annapolis holiday on Expedia.

Our guide on where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Annapolis featuring a city and street scenes as well as a small group of people

Historic District

2 out of top 10 points of interest in this area
5/5(2 area reviews)

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotel + flight trips in Historic District

Annapolis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
39,500
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Sandy Point State Park, Sandy Point Beach and Thanksgiving Farm Wines

Our pick of the best Annapolis Hotel Deals

DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 12 May to 13 May
AU$193
per night
12 May - 13 May
8.6/10 Excellent! (999 reviews)
Nice hotel
"One night stay while on our way north. Very clean, comfortable! Just what we needed! Great restaurant in the hotel!!"

Reviewed on 15 Apr. 2024

DoubleTree by Hilton Hotel Annapolis
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
The price is AU$283 per night from 13 May to 14 May
AU$283
per night
13 May - 14 May
8.8/10 Excellent! (1,603 reviews)
"Lovely historic Inn, excellent help, excellent valet."

Reviewed on 24 Apr. 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 5 May to 6 May
AU$297
per night
5 May - 6 May
9.2/10 Wonderful! (1,079 reviews)
"Complementary Valet parking"

Reviewed on 23 Apr. 2024

Graduate Annapolis
See all 553 properties in Annapolis
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
beach holidays

Beach Holidays

Beach Holidays
family friendly holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does an Annapolis holiday package cost?
From just . Yes, you read that correctly. Our Annapolis holiday packages are a great way to make your budget last longer. Bundle your favourite flights, hotels and rental car and get out and see this fabulous destination.
How do I get a cheap travel package to Annapolis?
Lock in flights that fit in with your schedule, add a hotel room to your booking and see how much you save with an Annapolis holiday package. It’s that simple! From hotels and flights to rental cars and activities, Expedia makes travelling cheap and easy. And with over 550 airlines and 1 000 000 hotel options globally to pick from, you’ll never be short of choice.
Where should I stay in Annapolis?
An escape to Annapolis isn’t complete without spending some time in Historic District, so why not get a hotel in this popular neighbourhood? That way, you’ll be handy to Maryland State House. If U.S. Naval Academy is high on your to-do list, stay in Naval Academy.
What are the top hotels in Annapolis?
Travellers journeying to Annapolis often stay in Historic District. Graduate Annapolis and Historic Inns of Annapolis are well-known options in this neighbourhood. But it’s not the only happening place around town! Eastport is another fantastic area and where you’ll find Crowne Plaza Annapolis, an IHG Hotel and DoubleTree by Hilton Hotel Annapolis.
How far in advance should I book my Annapolis holiday?
While not all air carriers release tickets early, it’s usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you’ll nab some fantastic deals. If you’re booking last minute, there’s a chance you could get lucky. Low prices occasionally become available a few weeks prior to departure.
What does an Expedia Annapolis travel package include?
Flights, rental cars and hotels, or any combination of the three — you decide! Whether you’re venturing to Annapolis on a family road trip or enjoying a solo break, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking an Annapolis travel package?
Our prices are always low. However, you’ll grab even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with an Annapolis Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the perfect carrier to get you to Annapolis will be a cinch.
If I'm not able to travel, can I cancel my Annapolis holiday package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can cancel or change your Annapolis holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Annapolis

Image for U.S. Naval Academy

U.S. Naval Academy

4/5(3 reviews)

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

U.S. Naval Academy
Image for Chesapeake Bay Bridge

Chesapeake Bay Bridge

5/5(1 review)

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Image for Sandy Point State Park

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

What to do in Annapolis

Image for Historic Annapolis Food Tour

Historic Annapolis Food Tour

AU$115
Per adult
Historic Annapolis Food Tour
Image for Half Day Private Bus Tour of Annapolis Up to 13 people

Half Day Private Bus Tour of Annapolis Up to 13 people

AU$2,568
Per adult
Half Day Private Bus Tour of Annapolis Up to 13 people
Image for Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

AU$45
Per adult
Phantoms of Annapolis Ghost Tour By US Ghost Adventures
See all activities in Annapolis

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.