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.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was CA $1,425, price is now CA $1,182 per person
CA $1,182
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.4/10 Very Good! (1,247 reviews)
Friendly courteous staff. Restaurant food needs improvement. Overall it was clean and decent.

Reviewed on Feb 18, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was CA $2,100, price is now CA $1,604 per person
CA $1,604
per person
May 11 - May 14
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Nice room, clean view of the water.

Reviewed on Feb 20, 2026

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was CA $2,105, price is now CA $1,689 per person
CA $1,689
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Nice room, enjoyed the hotel bar and restaurant and staff were friendly and helpful

Reviewed on Feb 16, 2026

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
Price was CA $1,644, price is now CA $1,349 per person
CA $1,349
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.6/10 Excellent! (1,006 reviews)
The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town.

Reviewed on Feb 11, 2026

Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

3.5 out of 5
Harbor East
Price was CA $1,807, price is now CA $1,513 per person
CA $1,513
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.2/10 Very Good! (2,405 reviews)
Friendly staff, clean rooms

Reviewed on Feb 23, 2026

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Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Beautiful troll downtown Annapolis... #Adventure

Historic District

2 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 $219 per night from Mar 2 to Mar 3
CA $219
CA $296 total
Mar 2 - Mar 3
includes taxes & fees
9/10 Wonderful! (1,890 reviews)
The room really showed its age. The entire room was tilted.... so much so that a bottle rolled on the floor from the left to the right without any push. The bed was likewise tilted and really difficult to sleep comfortably. The elevator was out of order, and there were older guests on the 3rd floor ...

Reviewed on Feb 23, 2026

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 CA $113 per night from Mar 8 to Mar 9
CA $113
CA $129 total
Mar 8 - Mar 9
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Food and bar was excellent rooms were clean and average but entire stay quite comfortable

Reviewed on Feb 23, 2026

DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Mar 8 to Mar 9
CA $221
CA $252 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
Friendly, clean

Reviewed on Feb 22, 2026

Graduate by Hilton Annapolis
See all 570 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

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

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

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

From haunted harbors to pirate hideouts, the ghosts of Annapolis await.

Ashes and Apparitions of Annapolis Ghost Tour

CA $44
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $55
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

CA $109
per adult
Historic Annapolis Food Tour
See all activities in Annapolis

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