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
per person
Aug. 16 - Aug. 18
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.2/10 Very Good! (1,183 reviews)
Everything was great!

Reviewed on May 27, 2024

Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
Fells Point
per person
Aug. 16 - Aug. 18
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9/10 Wonderful! (740 reviews)
This property is really beautiful. We loved the common area 9th floor terrace. Great location

Reviewed on May 26, 2024

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
per person
Aug. 16 - Aug. 18
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
9.4/10 Exceptional! (1,099 reviews)
The staff is amazing. I had an issue with air conditioning and they immediately fixed the situation.

Reviewed on May 27, 2024

The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

4.5 out of 5
Otterbein
per person
Aug. 16 - Aug. 18
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.6/10 Excellent! (1,518 reviews)
No complimentary breakfast

Reviewed on May 26, 2024

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
per person
Aug. 16 - Aug. 18
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
It was really close to the stadium and the view was amazing. Hotel services were great. Thank you to all the staff

Reviewed on May 23, 2024

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Annapolis which includes street scenes and a city as well as a small group of people

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 hotel + flight trips in Historic District

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
8.8/10 Excellent! (1,620 reviews)
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance."

Reviewed on May 27, 2024

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Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
8.6/10 Excellent! (1,004 reviews)
"Hhgggggg"

Reviewed on May 24, 2024

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Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,047 reviews)
"Very attractive hotel. All staff helpful. Breakfast cafe good and quick. Bed comfortable. Quiet."

Reviewed on May 26, 2024

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Graduate Annapolis
See all 562 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

Frequently asked questions

How much does an Annapolis vacation package cost?
From just CA $445. Yes, you read that correctly. Our Annapolis vacation packages are a great way to make your budget last longer. Bundle your favorite flights, hotels and rental car and get out and see this fabulous destination.
How do I get a cheap travel package to Annapolis?
Lock in flights that fit in with your schedule, add a hotel room to your booking and see how much you save with an Annapolis vacation package. It’s that simple! From hotels and flights to rental cars and activities, Expedia makes traveling cheap and easy. And with over 550 airlines and 1,000,000 hotel options globally to pick from, you’ll never be short of choice.
Where should I stay in Annapolis?
An escape to Annapolis isn’t complete without spending some time in Historic District, so why not get a hotel in this popular neighborhood? That way, you’ll be handy to Maryland State House. If U.S. Naval Academy is high on your to-do list, stay in Naval Academy.
What are the top hotels in Annapolis?
Travelers journeying to Annapolis often stay in Historic District. Graduate Annapolis and Historic Inns of Annapolis are well-known options in this neighborhood. But it’s not the only happening place around town! Eastport is another fantastic area and where you’ll find Crowne Plaza Annapolis, an IHG Hotel and DoubleTree by Hilton Hotel Annapolis.
How far in advance should I book my Annapolis vacation?
While not all air carriers release tickets early, it’s usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you’ll nab some fantastic deals. If you’re booking last minute, there’s a chance you could get lucky. Low prices occasionally become available a few weeks prior to departure.
What does an Expedia Annapolis travel package include?
Flights, rental cars and hotels, or any combination of the three — you decide! Whether you’re venturing to Annapolis on a family road trip or enjoying a solo break, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking an Annapolis travel package?
Our prices are always low. However, you’ll grab even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with an Annapolis Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the perfect carrier to get you to Annapolis will be a cinch.
If I'm not able to travel, can I cancel my Annapolis vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can cancel or change your Annapolis vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Annapolis

Image for U.S. Naval Academy

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
Image for 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
Image for 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

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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.