Annapolis Holidays

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to S$120 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis

Top hotels in Annapolis

Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$260 per night from 1 Apr to 2 Apr
S$260
per night
1 Apr - 2 Apr
9.2/10 Wonderful! (1,097 reviews)
Cheesy Preppy Decor but Comfy Beds
"The decor is very extra in its Annapolis theme - think Navy-inspired furniture and bathroom wallpaper with crabs on it. The outlet in our bathroom was broken so I had to do my hair at the bedroom desk using my reflection in the TV for a morning event. The bedding, however, is very comfortable and ..."

Reviewed on 27 Mar,2024

Graduate 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 S$265 per night from 10 Apr to 11 Apr
S$265
per night
10 Apr - 11 Apr
8.8/10 Excellent! (1,611 reviews)
A wonderful stay in every way
"Easy quick check in. The Inn is very unique and makes for a lovely stay. Very close to restaurants, shops and water attractions. The room was very clean and comfortable with everything necessary for a night away. We’ll definitely be back."

Reviewed on 25 Mar,2024

Historic Inns of Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
The price is S$260 per night from 4 Apr to 5 Apr
S$260
per night
4 Apr - 5 Apr
8.6/10 Excellent! (1,002 reviews)
"Always a nice stay!"

Reviewed on 25 Mar,2024

The Westin 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.

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.

Popular places to visit

What to do in Annapolis

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