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 by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Price was CA $683, price is now CA $595 per person
CA $595
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
The room was clean, staff was helpful and nice.

Reviewed on Feb 8, 2026

Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Price was CA $1,279, price is now CA $1,027 per person
CA $1,027
per person
May 15 - May 20
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
The hotel is under construction which was not listed on the website. The staff was not very courteous. The stay was okay. A bit disappointing since I have stayed at the Element in Hampton Roads which is excellent. I will not return to this location in the future.

Reviewed on Feb 15, 2026

Four Seasons Hotel Baltimore

Four Seasons Hotel Baltimore

5 out of 5
Harbor East
Price was CA $2,915, price is now CA $2,397 per person
CA $2,397
per person
May 15 - May 20
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9.6/10 Exceptional! (923 reviews)
I’ve stayed at many 5 star hotels and resorts when I travel but I was impressed with the attention to detail and

Reviewed on Feb 11, 2026

Baltimore Marriott Waterfront

Baltimore Marriott Waterfront

3.5 out of 5
Harbor East
Price was CA $2,061, price is now CA $1,705 per person
CA $1,705
per person
May 15 - May 20
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9.2/10 Wonderful! (1,002 reviews)
Everything was great!

Reviewed on Feb 16, 2026

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Price was CA $1,579, price is now CA $1,328 per person
CA $1,328
per person
May 15 - May 20
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9.2/10 Wonderful! (979 reviews)
Just wasn't to our liking. Rooms were clean and in good repair. Staff was very nice and curteous. Breakfast in the Ash Bar was great. It's a very old and dark hotel. Room was very dark and small. Card key was deactivated before checkout. Had to go back downstairs to get it reactivated. At least two others had the same issue.

Reviewed on Feb 20, 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

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 $232 per night from Feb 28 to Mar 1
CA $232
CA $264 total
Feb 28 - Mar 1
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Nice room, enjoyed the hotel bar and restaurant and staff were friendly and helpful

Reviewed on Feb 16, 2026

Graduate by Hilton 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 $212 per night from Feb 24 to Feb 25
CA $212
CA $289 total
Feb 24 - Feb 25
includes taxes & fees
9/10 Wonderful! (1,877 reviews)
We had a wonderful stay and really enjoyed it. The courtesy of the stuff was outstanding!

Reviewed on Feb 13, 2026

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Feb 22 to Feb 23
CA $135
CA $154 total
Feb 22 - Feb 23
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Would stay here again

Reviewed on Feb 15, 2026

Hilton Garden Inn Annapolis Downtown
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
Family Vacations
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.