Annapolis Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Annapolis vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Property amenity
    May 16 - May 20

    The Westin Baltimore Washington Airport - BWI

    Linthicum Heights
    4.0 star property
    8.6 Excellent (1,030)

    "Good Property. "

    Roundtrip Montreal (YUL) - Washington (DCA)
    YUL - DCANonstop DCA - YULNonstop
    CA $973
    CA $738
    per traveller
    found 5 hours ago
    The Westin Baltimore Washington Airport - BWI
  • Exterior
    May 16 - May 20

    Hampton Inn & Suites Baltimore Inner Harbor

    Downtown Baltimore
    2.5 star property
    8.6 Excellent (1,001)

    "Beautiful clean and accommodating "

    Roundtrip Montreal (YUL) - Washington (DCA)
    YUL - DCANonstop DCA - YULNonstop
    Save 100% on your flight
    CA $1,454
    CA $996
    per traveller
    found 5 hours ago
    Hampton Inn & Suites Baltimore Inner Harbor
  • Exterior detail
    May 16 - May 20

    Sonesta Hotel Baltimore Inner Harbor

    Downtown Baltimore
    2.5 star property
    8.8 Excellent (389)

    "Quick stop in Baltimore with the family. Sonesta wass a clean comfortable hotel in the heart of Baltimore. Staff were all friendly. Would stay there again"

    Roundtrip Montreal (YUL) - Washington (DCA)
    YUL - DCANonstop DCA - YULNonstop
    CA $1,351
    CA $1,005
    per traveller
    found 5 hours ago
    Sonesta Hotel Baltimore Inner Harbor
  • Lobby
    May 16 - May 20

    Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

    Downtown Baltimore
    4.5 star property
    8.0 Very good (1,002)

    "My domestic partner and I needed a change a spark. I booked a surprise getaway and this place provides great views and excellent food "

    Roundtrip Montreal (YUL) - Washington (DCA)
    YUL - DCANonstop DCA - YULNonstop
    CA $1,360
    CA $1,019
    per traveller
    found 5 hours ago
    Kimpton Hotel Monaco Baltimore Inner Harbor by IHG
  • Exterior
    May 16 - May 20

    Lord Baltimore Hotel

    Downtown Baltimore
    3.5 star property
    8.2 Very good (1,803)

    "Property is definitely aging and could use upgrades/renovation, but the beds were extremely comfortable and we enjoyed our stay. "

    Roundtrip Montreal (YUL) - Washington (DCA)
    YUL - DCANonstop DCA - YULNonstop
    CA $1,181
    CA $914
    per traveller
    found 5 hours ago
    Lord Baltimore Hotel

Where to stay in Annapolis

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.

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Spa Creek.

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

Frequently Asked Questions

How much does an Annapolis vacation package cost?

You can snap up a vacation package to this popular destination from CA $738 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.

Is it worth booking a vacation package to Annapolis?

Popular for its history, culture and watersports, an Annapolis vacation has something for everyone. Be sure to check out main sights like Annapolis City Dock and Westfield Annapolis Mall, and consider renting some wheels for day trips to explore even more.

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.

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