Annapolis Holidays

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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 featuring a city and street scenes as well as a small group of people

Historic District

1 out of top 10 points of interest in this area

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotels in Historic District

Top hotels in Annapolis

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! (1,824 reviews)
"Great place for a quick get away!"

Reviewed on 26 Jul 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 Rp2.603.185 per night from 17 Aug to 18 Aug
Rp2.603.185
Rp2.967.630 total
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,008 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 27 Jul 2025

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 Rp1.594.138 per night from 3 Aug to 4 Aug
Rp1.594.138
Rp1.817.318 total
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,019 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 27 Jul 2025

DoubleTree by Hilton Hotel Annapolis
See all 579 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.

What to do in Annapolis

Food Tour Plate

Historic Annapolis Food Tour

Rp1.305.600
per adult
Historic Annapolis Food Tour
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Rp161.072
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Annapolis: Ghosts of the Harbor & Old Town Tour

Annapolis: Pirates, Patriots, and Poltergeists of Old Town

Rp440.640
per adult
Annapolis: Pirates, Patriots, and Poltergeists of Old Town
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis holidays 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 neighbourhoods 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 holiday package to Annapolis?
Popular for its history, culture and watersports, an Annapolis holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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, favourite 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 holiday 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.