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Annapolis Vacation Packages

See sailing regattas, naval officers and red brick colonial mansions in the state of Maryland’s attractive capital city.

Annapolis is a laid-back place of narrow cobblestone streets, 18th-century brick buildings and colonial mansions and a proud naval heritage. Although now home to many high-tech industries, the city has retained its historic charm.

Situated on the south bank of the Severn River, the state capital of Maryland has been the center of marine activities for years. It’s a port and the site of the U.S. Naval Academy.

Annapolis was founded in 1649 by Puritan settlers and renamed Annapolis in 1694 after Princess Anne of Denmark and Norway. For 9 months between 1783 and 1784 it served as the nation’s first peacetime capital after the American Revolutionary War.

Make City Dock your first port of call. It’s the heart of the city’s waterfront. Walk along the promenade to view the boats, peruse the shops and dine in the restaurants and bars. Walk on the dock to see the memorial of Kunta Kinte’s arrival from Africa in 1767. His story was told in Alex Haley’s novel Roots.

The U.S. Naval Academy was founded here in 1845. Within its walls future naval officers undergo 4 years of training. Take a guided tour of the grounds where you’ll learn about the history of the academy and its traditions. Visit the U.S. Naval Academy History Museum and view medals, swords and multimedia presentations that chart the history of sea power and the development of the U.S. Navy.

Gain further insights into Annapolis’s history at Maryland State House, the oldest state house in the United States that’s still in legislative use. Stop by Chase-Lloyd House, the Georgian brick mansion that was constructed for Samuel Chase, one of the signatories to the Declaration of Independence.  

Annapolis is the gateway to Chesapeake Bay, and its shoreline is dotted with marinas. Get out on the water with a day cruise or charter your own boat. You can also rent canoes, kayaks and pedal boats. If you don’t want to get on the water you can enjoy it from land by watching one of the sailing races. From the end of April to early September there are sailboat races every Wednesday night. More than 150 boats sail around several markers in the bay before heading for the finish in front of the Annapolis Yacht Club. 

Annapolis is less than an hour’s drive from Washington D.C. and is a popular daytrip destination for visitors to the nation’s capital.

Accommodation in Annapolis

Make a booking for one of the 29 Annapolis lodging options available through Expedia's extensive Annapolis lodging page before you start your trip.

Why not start the quest for your dream Annapolis accommodation by checking out the guest amenities at the high-rating Loews Annapolis Hotel, located at 126 West St, and the DoubleTree by Hilton Hotel Annapolis, 210 Holiday Court. If those options don't grab you, the Westin Annapolis, 100 Westgate Cir, and the O'Callaghan Annapolis Hotel, 174 West St could be more to your taste.


Top Hotel Deals

See all 813 Hotels in Annapolis
C$133
Country Inn & Suites By Carlson Annapolis

Country Inn & Suites By Carlson Annapolis

2600 Housley Road, Annapolis
4.1
of 5, from 235 reviews
3.0 out of 5.0

Situated in a shopping district, this hotel is within 1 mi (2 km) of Annapolis Mall Shopping Center, Westfield Annapolis Mall, and Annapolis Bowl. Anne Arundel Medical Center and The Kunta Kinte Alex Haley Memorial are also within 2 mi (3 km).

C$259
Loews Annapolis Hotel

Loews Annapolis Hotel

126 West St, Annapolis
4.2
of 5, from 219 reviews
4.0 out of 5.0

This six-story brick hotel is 0.5 mile from the shops, restaurants, and historic sites of Annapolis and 1 mile from both the Naval Academy and City Dock on Chesapeake Bay.

C$133
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy, Bowie
4.3
of 5, from 186 reviews
3.0 out of 5.0

Situated in the business district, this hotel is within 1 mi (2 km) of Prince George's Stadium and Prince Georges Stadium. Allen Pond Park and National Capital Radio and Television Museum are also within 3 mi (5 km).

C$110
Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis
3.4
of 5, from 380 reviews
2.5 out of 5.0

Situated in the business district, this hotel is within 1 mi (2 km) of The Kunta Kinte Alex Haley Memorial, Westfield Annapolis Mall, and Annapolis Mall Shopping Center. Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are also within 1 mi (2 km).

C$97
Extended Stay America Annapolis - Admiral Cochrane Drive

Extended Stay America Annapolis - Admiral Cochrane Drive

120 Admiral Cochrane Dr, Annapolis
2.5
of 5, from 82 reviews
2.5 out of 5.0

Situated in Annapolis, this hotel is within 1 mi (2 km) of Annapolis Harbour Center, The Kunta Kinte Alex Haley Memorial, and Westfield Annapolis Mall. Annapolis Mall Shopping Center and Annapolis Harbor Center Shopping Center are also within 2 mi (3 km).

C$133
Crowne Plaza Annapolis

Crowne Plaza Annapolis

173 Jennifer Rd, Annapolis
3.9
of 5, from 375 reviews
3.5 out of 5.0

Located in the business and shopping district of Annapolis, this hotel is a newly renovated, upscale, full-service hotel and conference center.

C$199
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle, Annapolis
4.1
of 5, from 457 reviews
3.5 out of 5.0

These central Annapolis inns, located within a half-mile (.8 kilometers) of the US Naval Academy, comprise 3 buildings: the 1727 Governor Calvert House, the 1772 Robert Johnson House, and the 1776 Maryland Inn.

C$143
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

189 Admiral Cochrane Drive, Annapolis
4.5
of 5, from 156 reviews
3.0 out of 5.0

Situated in Annapolis, this hotel is within 1 mi (2 km) of Annapolis Harbour Center and Annapolis Harbor Center Shopping Center. The Kunta Kinte Alex Haley Memorial and Westfield Annapolis Mall are also within 2 mi (3 km).

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