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
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

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.

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A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

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

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A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

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

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A grassy area with two Adirondack chairs near a waterfront, a large tree, and a distant view of the sea.

Hillsmere

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

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Admiral Heights

Admiral Heights might not have many top sights, but Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts are two attractions nearby that you can check out.

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Find the Best Annapolis Vacation Packages

Annapolis Hotel Deals

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
SAR 366
SAR 418 total
27 Sep - 28 Sep
includes taxes & fees
8.8/10 Excellent! (1,134 reviews)
"Nice staff. Truly always enjoy my stay"

Reviewed on 29 August 2026

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
SAR 398
SAR 582 total
29 Sep - 30 Sep
includes taxes & fees
Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD
Fully refundable
SAR 364
SAR 415 total
13 Sep - 14 Sep
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Large room"

Reviewed on 28 August 2026

Crowne Plaza Annapolis by IHG
See all 562 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.

Stay near popular Annapolis attractions

A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.

Sandy Point State Park

8.6/10 (221 reviews)
Sandy Point State Park offers pristine Chesapeake Bay beachfront beneath the towering Bay Bridge. Visitors can launch boats, fish for striped bass, or attend the renowned Maryland Seafood Festival.
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A beach with two people, a large suspension bridge in the background.

Chesapeake Bay Bridge

8.8/10 (1,066 reviews)
This 4.3-mile engineering marvel connects Maryland's shores while offering spectacular panoramic bay views. Drive across at sunrise to witness the Chesapeake's shimmering waters dotted with sailboats below.
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A statue on a pedestal labeled "DEKALB" in front of a brick building with a clock tower.

Maryland State House

9.0/10 (433 reviews)
After visiting Maryland State House, make a plan to see the other sights and activities in Annapolis. While you're in the area, stroll along the waterfront.
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A white building with a dome, surrounded by lush greenery and a well-maintained garden with pathways and benches.

William Paca House

8.6/10 (24 reviews)
Find out about the history of Annapolis when you take a trip to William Paca House. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.
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Navy-Marine Corps Memorial Stadium

9.2/10 (287 reviews)
Home to the Navy Midshipmen teams, this stadium honors naval service members with its impressive Memorial Plaza. Catch the vibrant atmosphere of a fall football game or the annual Annapolis Crab Feast in August.
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Maryland Renaissance Festival

10.0/10 (1 review)
Step back in time at this sprawling 16th-century English village recreation with over 200 performers. Watch jousting tournaments, sample period foods like turkey legs, and browse 140 artisan craft shops.
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Westfield Annapolis Mall

8.8/10 (394 reviews)
Westfield Annapolis offers over 200 stores, from luxury boutiques to popular department stores. Explore high-end fashion, dine at diverse restaurants, or catch a film at the state-of-the-art theater.
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Sandy Point Beach

9.6/10 (10 reviews)
Sandy Point State Park features a mile-long beach with Bay Bridge views on the Chesapeake. Enjoy swimming in calm waters, launch a boat from the marina, or experience the September Seafood Festival.
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Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices on Expedia for your Annapolis escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Annapolis costs.
What are the cheapest months to go to Annapolis?
You can typically find lower rates and greater availability in January, February and March. Browse our cheap Annapolis vacation packages and you could land some great off-season discounts.
How to find the best Annapolis package deals?
Landing a cheap Annapolis package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Annapolis package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Annapolis vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can tailor your Annapolis getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Annapolis?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Annapolis adventure.
How to plan a trip to Annapolis?
  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Annapolis.
  2. Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may arise during your trip to Annapolis.
  3. Decide how long to go for: Now that you're up to speed on Annapolis, you can figure out the right length of your vacation. Pull together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Annapolis vacation package.