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.
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
Price was CA $1,040, price is now CA $882 per person
CA $882
per person
Apr 19 - Apr 23
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
7.8/10 Good! (320 reviews)
Room was clean but the shower didn’t work but they gave me another room right away

Reviewed on Feb 10, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was CA $1,969, price is now CA $1,536 per person
CA $1,536
per person
Apr 12 - Apr 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Staff and room were amazing

Reviewed on Feb 7, 2026

Sonesta Select Greenbelt College Park

Sonesta Select Greenbelt College Park

3 out of 5
Price was CA $1,053, price is now CA $900 per person
CA $900
per person
Apr 19 - Apr 23
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
7.8/10 Good! (1,186 reviews)
Clean room hot water

Reviewed on Jan 23, 2026

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
Price was CA $1,660, price is now CA $1,440 per person
CA $1,440
per person
Apr 19 - Apr 23
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.4/10 Very Good! (1,002 reviews)
Great customer service

Reviewed on Feb 11, 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.

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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 $112 per night from Feb 22 to Feb 23
CA $112
CA $128 total
Feb 22 - Feb 23
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Staff-clean room

Reviewed on Feb 8, 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
9/10 Wonderful! (1,886 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!

Reviewed on Jan 31, 2026

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Historic Inns of 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 $223 per night from Feb 23 to Feb 24
CA $223
CA $254 total
Feb 23 - Feb 24
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Clean comfortable room!

Reviewed on Feb 8, 2026

Graduate by Hilton Annapolis
See all 568 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.