Annapolis Vacations from ￥193,074

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Tru By Hilton Baltimore Harbor East, MD

Tru By Hilton Baltimore Harbor East, MD

2.5 out of 5
Little Italy
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.2/10 Wonderful! (1,006 reviews)
Great property. Will stay there again. Walkable to Fells Point and Little Italy. The only items that could be improved are quieter room doors. If your neighbor gets up early, you’ll hear the door slam shut. Also, the breakfast could have a few more hot options. Plenty of cold option, though.

Reviewed on Aug 10, 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
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.2/10 Wonderful! (75 reviews)
Had breakfast in the restaurant 2 mornings and was surprised that couldn’t get a Bloody Mary. The restaurant is open early but they don’t sell alcohol until 11am for some reason.

Reviewed on Aug 10, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8.6/10 Excellent! (1,001 reviews)
The property is clean. Street parking is difficult so you can park at valet for $50

Reviewed on Aug 13, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8.2/10 Very Good! (653 reviews)
Great location, nice and quite stay!

Reviewed on Aug 12, 2025

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
Great hotel & friendly staff. Clean & comfortable bed.

Reviewed on Aug 7, 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

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
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,829 reviews)
"Charming area and loved to hotel decor!"

Reviewed on Aug 11, 2025

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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 ￥23,742 per night from Sep 3 to Sep 4
￥23,742
￥27,067 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Big rooms. Darkening curtains. Clean. Nice"

Reviewed on Aug 12, 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 ￥14,321 per night from Aug 21 to Aug 22
￥14,321
￥16,327 total
Aug 21 - Aug 22
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."

Reviewed on Aug 7, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 580 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

￥11,792
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

￥3,840
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

￥4,431
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 ￥193,074 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.