Annapolis Vacation Packages

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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.
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $501, price is now CA $414 per person
CA $414
per person
Nov 22 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Great stay. Nice quiet room.

Reviewed on Aug. 28, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
Price was CA $851, price is now CA $623 per person
CA $623
per person
Oct 11 - Oct 14
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
This was a very nice place to stay while we were in the area for both work and pleasure

Reviewed on Sep. 3, 2025

Baltimore Marriott Waterfront

Baltimore Marriott Waterfront

3.5 out of 5
Harbor East
Price was CA $717, price is now CA $579 per person
CA $579
per person
Nov 22 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (1,022 reviews)
The Marriott company's inflexibility regarding a booking error on my part, that I strongly feel the Expedia website contributed to, is going to cost both companies a customer going forward. The Expedia company's customer service inability to help with this issue is extremely disappointing.

Reviewed on Sep. 2, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Price was CA $1,017, price is now CA $837 per person
CA $837
per person
Oct 4 - Oct 7
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (713 reviews)
The balcony view was great!

Reviewed on Sep. 3, 2025

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
Inner Harbor
Price was CA $663, price is now CA $550 per person
CA $550
per person
Nov 22 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (2,318 reviews)
I loved everything about this hotel, from the check in to the amenities and even the check out. Monet and Tony at the restaurant where the best. Tony's hospitality is unbeatable and Monet can serve a mean omelet. It was so delicious!!!. Parking is located right under the hotel and allows in and outs. No need for a pass or window ticket. It just scans your licenses plate. Will be back!!!!

Reviewed on Sep. 3, 2025

Where to stay in Annapolis

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

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

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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
The price is CA $159 per night from Sep 14 to Sep 15
CA $159
CA $229 total
Sep 14 - Sep 15
includes taxes & fees
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is CA $155 per night from Sep 16 to Sep 17
CA $155
CA $176 total
Sep 16 - Sep 17
includes taxes & fees
Crowne Plaza Annapolis by IHG
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is CA $140 per night from Sep 14 to Sep 15
CA $140
CA $159 total
Sep 14 - Sep 15
includes taxes & fees
Country Inn & Suites by Radisson, Annapolis, MD
See all 585 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.
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Discover the most popular places to visit in Annapolis

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

U.S. Naval Academy

4.5/5(8 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
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4.5/5(2 reviews)

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

Chesapeake Bay Bridge
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

Food Tour Plate

Historic Annapolis Food Tour

CA $110
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

CA $44
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $41
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.