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.
Springhill Suites Marriott Baltimore Downtown/Inner Harbor

Springhill Suites Marriott Baltimore Downtown/Inner Harbor

3 out of 5
Downtown Baltimore
per person
Jan. 24 - Jan. 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
Great experience and staff!

Reviewed on Dec. 14, 2024

Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
per person
Mar. 8 - Mar. 14
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
9/10 Wonderful! (609 reviews)
This hotel was like stepping back in time like, but modernized where it counts. I felt like I was in a movie from old days. Comfy bed, good shower, views, all good.

Reviewed on Dec. 20, 2024

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
per person
Jan. 24 - Jan. 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.4/10 Very Good! (319 reviews)
Great location! Walkable to everything in the Inner Harbor area. Close parking-garage fee was $36 for 24 hours.

Reviewed on Dec. 22, 2024

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
per person
Mar. 8 - Mar. 14
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
8.2/10 Very Good! (1,654 reviews)
1 mile to stadiums. Great staff. Room kept clean. Wonderful stay.

Reviewed on Dec. 23, 2024

Hampton Inn & Suites Columbia South Fort Meade Area

Hampton Inn & Suites Columbia South Fort Meade Area

2.5 out of 5
per person
Jan. 24 - Jan. 31
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,004 reviews)
Convenient, clean, and great customer service

Reviewed on Dec. 22, 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

Ready to book your vacation to Annapolis?

 

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Annapolis Hotel Deals

Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is CA $158 per night from Dec. 25 to Dec. 26
CA $158
CA $180 total
includes taxes & fees
Dec 25 - Dec 26
8.6/10 Excellent! (1,003 reviews)
"Easy on and off the highway"

Reviewed on Dec. 20, 2024

Crowne Plaza Annapolis, an IHG Hotel
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 $218 per night from Dec. 30 to Dec. 31
CA $218
CA $249 total
includes taxes & fees
Dec 30 - Dec 31
9.2/10 Wonderful! (1,004 reviews)
Quick overnight
"This hotel is clean, well-maintained and well decorated. It is situated right in Annapolis. The only downside is that parking isn’t included and is expensive, at least $30/night."

Reviewed on Dec. 21, 2024

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 $221 per night from Dec. 26 to Dec. 27
CA $221
CA $300 total
includes taxes & fees
Dec 26 - Dec 27
8.8/10 Excellent! (1,707 reviews)
"Historic and gorgeous"

Reviewed on Dec. 21, 2024

Historic Inns of Annapolis
See all 563 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?
You can snap up a vacation package to this popular destination from CA $751 on Expedia. However, how much your vacation to Annapolis costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Annapolis?
You’re likely to find lower prices and greater availability in January, February and March. Take a look at our cheap Annapolis vacation packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis vacations come in various shapes and sizes, but to get a real feel for this destination, we think 2 days is a good ballpark. In this timeframe, you can visit major attractions like Bay Ridge Beach and Annapolis Bowl along with lesser-known gems. Don’t forget to explore neighborhoods such as Parole and Historic District either. If you’re smart with your time, you can even schedule a day trip from Annapolis too.
How to find the best Annapolis package deals?
Finding a cheap Annapolis package deal is a breeze with Expedia. After you’ve entered your destination and preferred dates under our “Packages” tab, set your budget, add a few filters and browse what’s available. You can tailor your search by “Area,” “Amenities,” “Property type” and more. Sort the results by “Price: low to high” to discover the most pocket-friendly Annapolis package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Annapolis vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You’ll generally land a better deal than booking each component separately. And you’ll still enjoy the flexibility to create a tailored Annapolis vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Annapolis?
If you’re considering a spontaneous Annapolis adventure, browse our last-minute deals that can be booked up to a week before you take off. Don’t want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Annapolis?

  1. Pick the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Annapolis.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to put aside for your trip to Annapolis. Then, choose a property that matches your budget, whether that’s a wallet-friendly option or a more luxurious retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you’d like to get to in Annapolis. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that’s left is to pick an Annapolis vacation package that brings all your bookings together.

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

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $50
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Step into the shadows and discover the haunting tales of our city's past.

Annapolis Ghost Tour: Phantoms of Annapolis

CA $36
per adult
Annapolis Ghost Tour: Phantoms of Annapolis
Food Tour Plate

Historic Annapolis Food Tour

CA $115
per adult
Historic Annapolis Food Tour
See all activities in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.