Annapolis Holidays

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Top Flight + Hotel Deals in Annapolis

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Price was €2,155, price is now €1,745 per person
€1,745
per person
17 Aug - 23 Aug
found 1 day ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,902 reviews)
Total convivence STATION TO EVRYTHING RT OUT THE DOOR

Reviewed on 12 Jul 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was €2,223, price is now €1,832 per person
€1,832
per person
17 Aug - 23 Aug
found 1 day ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
The property staff was awesome. Had a problem with TV and never fixed but staff did offer a change of rooms which I did not accept.

Reviewed on 11 Jul 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was €2,388, price is now €2,032 per person
€2,032
per person
17 Aug - 23 Aug
found 1 day ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
9/10 Wonderful! (1,206 reviews)
Poco confortable

Reviewed on 11 Jul 2026

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was €2,140, price is now €1,833 per person
€1,833
per person
17 Aug - 23 Aug
found 1 day ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
9.2/10 Wonderful! (1,007 reviews)
Great location and nice spacious room - A/C was out third night with no notification from staff and the water station did not work on our floor.. unacceptable in the extreme heat. Housekeeping did not do a great job.

Reviewed on 9 Jul 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was €2,103, price is now €1,807 per person
€1,807
per person
17 Aug - 23 Aug
found 1 day ago
Return flight included
Casablanca (CMN) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Everything was great

Reviewed on 11 Jul 2026

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

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
The price is €126 per night from 19 Jul to 20 Jul
€126
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (1,898 reviews)
"The Inn is actually 3 different properties. The check in process and waiting for shuttle to offsite properties is not convenient especially in the rain. The staff is not very friendly. They don't offer early check in or late check out. That being said, the properties are super convenient and well ..."

Reviewed on 12 Jul 2026

Historic Inns of 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 €111 per night from 13 Jul to 14 Jul
€111
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (1,033 reviews)
"This hotel is the best I’ve ever been to. The most extraordinary thing about this hotel is the staff. I would especially like to commend Antoine, Shuttle Driver and Amari at the front desk for going above and beyond their duties to help me during my stay! They are remrkably kind and considerate and ..."

Reviewed on 12 Jul 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is €118 per night from 27 Jul to 28 Jul
€118
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"Allergen room was clean and the bed was comfortable"

Reviewed on 11 Jul 2026

Crowne Plaza Annapolis by IHG
See all 558 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.
See properties

What to do in Annapolis

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

€26
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

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

€8
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

€31
per adult
Ashes and Apparitions of Annapolis Ghost Tour
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 from €1,745 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.