Annapolis Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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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 18 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.4/10 Very Good! (1,354 reviews)
Friendly staff, clean hotel, good food served at hotel restaurant.

Reviewed on Jul. 12, 2025

The William Fell Baltimore, Tapestry Collection by Hilton

The William Fell Baltimore, Tapestry Collection by Hilton

3.5 out of 5
Fells Point
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (29 reviews)
Nicely remodeled property. Great staff

Reviewed on Jun. 29, 2025

Budget Plaza Motel

Budget Plaza Motel

2 out of 5
Brooklyn
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
6.6/10 (32 reviews)
The cleaning compound used made the first room uninhabitable. Broken door.

Reviewed on Nov. 18, 2023

Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
Fells Point
per person
Sep 19 - Sep 22
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9/10 Wonderful! (1,005 reviews)
Beautiful hotel, right on the water. Cost $115 extra to park there for 2 nights.

Reviewed on Jul. 12, 2025

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
per person
Sep 19 - Sep 22
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
Very close to a lot of entertainment and dining. Staff was friendly and welcoming.

Reviewed on Jul. 11, 2025

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

1 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

Ready to book your vacation to Annapolis?

 

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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 $140 per night from Jul 20 to Jul 21
CA $140
CA $206 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,802 reviews)
"Our stay was fabulous! I loved the scent as you walked through the lobby door, I loved the historical components, all of the staff were super friendly, and I loved how close it was to walk downtown and by the dock."

Reviewed on Jul. 11, 2025

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 $212 per night from Aug 3 to Aug 4
CA $212
CA $242 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"Very nice property the rooms were great as was he service!"

Reviewed on Jul. 7, 2025

Graduate by Hilton 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 $140 per night from Aug 3 to Aug 4
CA $140
CA $159 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"It was very convenient for a stop over for our trip to Ocean City. The hotel was clean and the staff was great."

Reviewed on Jul. 7, 2025

DoubleTree by Hilton Hotel Annapolis
See all 581 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

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
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
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

Food Tour Plate

Historic Annapolis Food Tour

CA $110
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

CA $13
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Annapolis: Ghosts of the Harbor & Old Town Tour

CA $37
per adult
Annapolis: Ghosts of the Harbor & Old Town Tour
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $517 on Expedia for your Annapolis escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
You can typically find lower rates and greater availability in January, February and March. Browse our cheap Annapolis vacation packages and you could land some great off-season discounts.
How many days is enough for Annapolis?
To get the most out of an Annapolis vacation, we suggest booking for 2 days. Split your time between discovering Annapolis City Dock, Westfield Annapolis Mall and other well-known attractions, as well as experiencing neighbourhoods like Parole and Historic District. If you've got some time to spare, include a day trip or tour in your Annapolis vacation itinerary.
Is it worth booking a vacation package to Annapolis?
Whether you want to visit key attractions such as Annapolis City Dock and Westfield Annapolis Mall on your Annapolis vacation, or coming for its great history, culture and watersports, there's something for everyone here. With so much to see and do, you'll soon find out why so many visitors think Annapolis is a good vacation destination.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can tailor your Annapolis getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Annapolis?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Annapolis adventure.
How to plan a trip to Annapolis?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Annapolis.
  2. Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Annapolis.
  3. Decide how long to go for: Now that you're up to speed on Annapolis, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Annapolis vacation package.

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