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
8.8/10 Excellent! (1,821 reviews)
"I loved my stay at the Maryland Inn. Check in and valet is done at nearby Governor Calvert House. A quick 5 minute walk to your hotel follows. I had the standard double which was fine. My friend had the king and her room was easily twice the size of mine. Bed was very comfy, decor is top notch. I ..."

Reviewed on 2025/7/26

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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 NT$4,706 per night from Aug 17 to Aug 18
NT$4,706
NT$5,365 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Beautiful place, very clean room, but the best thing by far was the staff. Everyone we met was friendly and helpful. Thank you so much for a greay stay!!"

Reviewed on 2025/7/27

Graduate by Hilton Annapolis
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 NT$2,890 per night from Aug 3 to Aug 4
NT$2,890
NT$3,294 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,018 reviews)
7 out of 10 stars
"The hotel is older and as we walked through we were saying how it could be (& you can tell it was) a really nice hotel. Don’t misunderstand, it was a nice hotel, but you can tell it’s ‘used’. There are scuffs on doors and walls, there are tiles broken on floors, etc. the room itself was clean. The ..."

Reviewed on 2025/7/27

DoubleTree by Hilton Hotel Annapolis
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
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
Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters 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 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.