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.
Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Price was CA $980, price is now CA $706 per person
CA $706
per person
Jul 11 - Jul 15
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9.2/10 Wonderful! (1,445 reviews)
The staff was very helpful and pleasant

Reviewed on May 22, 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Price was CA $1,528, price is now CA $1,071 per person
CA $1,071
per person
Jul 18 - Jul 22
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9.4/10 Exceptional! (1,006 reviews)
If you're looking at this hotel, go ahead and book it! Not only is it luxurious and friendly, but you'll find at least 5 taxis by it at any time (a definite plus when certain Metro lines are being repaired). Added bonus: the signature house fragrance is unspeakably delicious. You will love your stay here!

Reviewed on Apr 29, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $1,219, price is now CA $897 per person
CA $897
per person
Jul 11 - Jul 15
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9/10 Wonderful! (809 reviews)
The ada accessible shower was poorly set up. The shower head locations were in bad places for access in relation to the shower chair. As well the soap tray was in a bad place. Beds were comfortable, bedding not so much. Need to have fitted 100% cotton sheets, not microfiber. Overall a nice room with plenty of space.

Reviewed on May 23, 2026

The River Inn

The River Inn

4 out of 5
Northwest
Price was CA $1,048, price is now CA $781 per person
CA $781
per person
Jul 11 - Jul 15
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9.4/10 Exceptional! (1,946 reviews)
Hotel staff can only be described as: extremely helpful, accommodating, diligent and proactive. Our 7 day stay at River inn was a blast for both of us and we will be staying at this particular venue again, when visiting DC

Reviewed on May 21, 2026

The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
Bethesda Downtown
Price was CA $958, price is now CA $719 per person
CA $719
per person
Jul 18 - Jul 22
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.6/10 Excellent! (1,858 reviews)
Very good location, great fitness center (well equipped, spacious), well-maintained common areas, comfortable room. Staff was generally helpful.

Reviewed on May 23, 2026

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Aerial Panoramic View Annapolis Maryland State House Capital City

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

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 $151 per night from May 31 to Jun 1
CA $151
CA $172 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"It was one of the nicest places we've stayed in our travels."

Reviewed on May 22, 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
The price is CA $161 per night from Jun 8 to Jun 9
CA $161
CA $230 total
Jun 8 - Jun 9
includes taxes & fees
9/10 Wonderful! (1,845 reviews)
"Charming historical site!"

Reviewed on May 24, 2026

Historic Inns of Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jun 7 to Jun 8
CA $163
CA $186 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"A good stay"

Reviewed on May 23, 2026

Courtyard by Marriott 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
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Family Vacations

Discover the most popular places to visit in Annapolis

U.S. Naval Academy

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
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
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

What to do in Annapolis

Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $36
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
Historic Annapolis Food Tour

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.