Annapolis Vacations from ￥173,940

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was ￥177,456, price is now ￥173,940 per person
￥173,940
per person
Oct 29 - Oct 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Expected more from a sheraton

Reviewed on Aug 25, 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was ￥180,574, price is now ￥175,128 per person
￥175,128
per person
Oct 29 - Oct 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (1,831 reviews)
Perfect location and beautiful, old building. Love the history of the building!

Reviewed on Aug 26, 2025

Hotel Revival Baltimore

Hotel Revival Baltimore

4 out of 5
Mount Vernon
Price was ￥181,539, price is now ￥176,148 per person
￥176,148
per person
Oct 29 - Oct 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
9.4/10 Exceptional! (1,006 reviews)
Beautiful hotel, dining options were delicious, walkable and transit-able!

Reviewed on Aug 27, 2025

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Price was ￥179,134, price is now ￥174,818 per person
￥174,818
per person
Oct 29 - Oct 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
9.2/10 Wonderful! (925 reviews)
Great hotel! We loved our stay!

Reviewed on Aug 25, 2025

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was ￥181,461, price is now ￥177,176 per person
￥177,176
per person
Oct 29 - Oct 30
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Baltimore (BWI)
8.2/10 Very Good! (2,152 reviews)
Everything was perfect for my stay

Reviewed on Aug 26, 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
5/5(83 area reviews)

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

Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
8.8/10 Excellent! (1,745 reviews)
"Perfect location and beautiful, old building. Love the history of the building!"

Reviewed on Aug 26, 2025

Get rates
Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
The price is ￥23,688 per night from Sep 3 to Sep 4
￥23,688
￥27,004 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Very good"

Reviewed on Aug 20, 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ￥14,915 per night from Sep 2 to Sep 3
￥14,915
￥17,003 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Great"

Reviewed on Aug 24, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 582 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.

Discover the most popular places to visit in Annapolis

U.S. Naval Academy which includes military items, interior views and heritage architecture

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
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
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

￥11,824
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

￥3,843
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

￥4,434
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination from ￥173,940 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.