Annapolis Vacations

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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.

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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! (1,823 reviews)
"Lovely room. Comfortable bed."

Reviewed on 13 August 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 AED 590 per night from Sep 2 to Sep 3
AED 590
AED 673 total
2 Sep - 3 Sep
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Upscale hotel, great location, walkable"

Reviewed on 15 August 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 refundable
The price is AED 356 per night from Aug 24 to Aug 25
AED 356
AED 406 total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"It was construction going on. One of the nights I stayed they were out there after 9 o'clock pm and that's my bedtime lol! The breakfast was good. They had a very good selection. My room was clean, no issues. I would say that they should at least upgrade the tv's. Overall my stay was good."

Reviewed on 16 August 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

Take a campus tour or just explore the area of U.S. Naval Academy, during your trip to Naval Academy. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

Find out about the history of Annapolis with a stop at Chesapeake Bay Bridge. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

Enjoy a trip to Sandy Point State Park and popular activities like boating in Annapolis. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Sandy Point State Park

Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination 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 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.