Annapolis Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AED 148 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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
Annapolis which includes street scenes and a city as well as a small group of people

Historic District

1 out of top 10 points of interest in this area
5/5(83 area reviews)

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Find hotels in Historic District

Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

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! (1,898 reviews)
Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking.

Reviewed on 11 December 2025

Get rates
Historic Inns of Annapolis
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 AED 280 per night from Dec 28 to Dec 29
AED 280
AED 319 total
28 Dec - 29 Dec
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
Great

Reviewed on 9 December 2025

DoubleTree by Hilton Hotel 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 AED 652 per night from Dec 21 to Dec 22
AED 652
AED 744 total
21 Dec - 22 Dec
includes taxes & fees
8.8/10 Excellent! (881 reviews)
Fantastic hotel and they upgraded us to a room with a stunning view!

Reviewed on 8 December 2025

Annapolis Waterfront Hotel, Autograph Collection
See all 560 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.

Discover the most popular places to visit in Annapolis

U.S. Naval Academy which includes military items, interior views and heritage architecture

U.S. Naval Academy

4.5/5(446 reviews)

Take a campus tour or just explore the area of U.S. Naval Academy, during your trip to Naval Academy. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4/5(270 reviews)

Find out about the history of Annapolis with a stop at Chesapeake Bay Bridge. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

4.5/5(13 reviews)

Enjoy a trip to Sandy Point State Park and popular activities like boating in Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Sandy Point State Park

Frequently asked questions

How do I find cheap flights to Annapolis that have flexible change policies?
At Expedia, we've been channeling our inner yogi to offer you the most flexible airfares in town. Just check the "No change fee" box directly underneath the "Flexible change policies" filter to find the best flights to Annapolis.
Which airlines fly to Annapolis?
Traveling to Annapolis is nice and easy. All you need to do is book a fare with one of these two popular carriers:

  • American Airlines - 7,267 flights to or near Annapolis each month, including 6,885 flights to Ronald Reagan Washington National Airport (DCA) and 381 to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) per month.
  • Delta Air Lines - 1,646 flights to or near Annapolis each month, including 1,304 flights to Ronald Reagan Washington National Airport (DCA) and 342 to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) per month.

How can I find cheap tickets to Annapolis?
Book well in advance, consider alternative airports, use frequent flyer miles — there are lots of ways! One more is to make the most of Expedia's "flexible dates" feature. Search for your Annapolis flight, then compare the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Annapolis was .
How much is a flight to Annapolis?
In the last seven days, return airfares to Annapolis sold from just and reached a maximum of . For one-way journeys departing from (), the lowest price during this time was just .
What are the most popular airports to fly into in Annapolis?
Depending on your carrier and city of departure, one of these busy airports will be your entry point to Annapolis:

  • Ronald Reagan Washington National Airport (DCA) - 11,147 flights per month.
  • Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 7,783 flights per month.

When is the cheapest time to fly to Annapolis?
Consider traveling earlier in the week to nab a bargain airfare to Annapolis. Tuesday is generally the most economical day to depart, with Monday a close second. Saturday typically has the highest ticket prices. This is because lots of people prefer to begin their vacation on a weekend.
How much is a plane ticket to Annapolis?
In the last seven days, airfares to Annapolis fluctuated from to .
What months are the cheapest to book a flight to Annapolis?
To bag a bargain flight to Annapolis, try to book during the month of February when airfares are at their cheapest. When's the most expensive time? In the U.S, it's the festive month of December.
How long is a flight to Annapolis?
Whether or not you'll have time for a movie marathon depends on where you're flying from in the States. To make organizing your trip a little easier, here are the average flight times for some well-known domestic routes to Annapolis:

  • Boston, MA (BOS-Logan Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 44 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 46 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Ronald Reagan Washington National Airport (DCA) - 1 hour and 51 minutes