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.

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
The price is AED 531 per night from Mar 10 to Mar 11
AED 531
AED 727 total
includes taxes & fees
10 Mar - 11 Mar
8.8/10 Excellent! (1,723 reviews)
"Superb location. Very nice rooms with ample space and great decor. Friendly and responsive staff. There were a couple items that kept it from 5 star. The hotel hosts many outside events in their ballroom during the day and the only access is through the main lobby. Attendees walk through the small ..."

Reviewed on 26 February 2025

Historic Inns of Annapolis
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 AED 327 per night from Mar 9 to Mar 10
AED 327
AED 373 total
includes taxes & fees
9 Mar - 10 Mar
8.6/10 Excellent! (1,005 reviews)
"Stayed for one night here at the Crowne and had a great stay. The room was nice with comfy beds. The hotel was near lots of restaurants and had its own bar restaurant as well. Food was decent. Downtown Annapolis is only about 10 minutes away. Would definitely stay here again when in Annapolis."

Reviewed on 2 March 2025

Crowne Plaza Annapolis, an IHG Hotel
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AED 340 per night from Mar 9 to Mar 10
AED 340
AED 388 total
includes taxes & fees
9 Mar - 10 Mar
8.4/10 Very Good! (1,002 reviews)
"Shuttle service to the harbor area is a big plus"

Reviewed on 1 March 2025

DoubleTree by Hilton Hotel Annapolis
See all 564 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.

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.

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

4.5/5(446 reviews)

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

4/5(270 reviews)

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

4.5/5(13 reviews)

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