Annapolis Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Annapolis Vacation

Book a custom vacation package to Annapolis and get ready to experience this fascinating city how you like. Consider spending time in the neighborhood of Historic District, which is good for history and tons more. If a sightseeing tour is part of the program during your trip to Annapolis, stop by leading attractions like U.S. Naval Academy, Maryland State House and William Paca House. Check out Expedia's wide range of travel options and book your ideal vacation to Annapolis now.

Top Annapolis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Hive
Fairmont Washington, D.C., Georgetown
Kimpton Banneker Hotel by IHG
The River Inn
The Bethesdan Hotel, Tapestry Collection by Hilton

Where to stay in Annapolis

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

Ready to book your vacation to Annapolis?

 

Choose your dates

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 CA $151 per night from May 31 to Jun 1
CA $151
CA $172 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"It was one of the nicest places we've stayed in our travels."

Reviewed on May 22, 2026

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 CA $161 per night from Jun 8 to Jun 9
CA $161
CA $230 total
Jun 8 - Jun 9
includes taxes & fees
9/10 Wonderful! (1,845 reviews)
"Charming historical site!"

Reviewed on May 24, 2026

Historic Inns of Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jun 7 to Jun 8
CA $163
CA $186 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"A good stay"

Reviewed on May 23, 2026

Courtyard by Marriott 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

What to do in Annapolis

Explore a world of travel with Expedia

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