Annapolis Vacation Packages

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Your Annapolis Vacation

Book a custom vacation package to Annapolis and get ready to experience this fascinating city how you like. Consider spending time in the neighborhood of Historic District, which is good for history and tons more. If a sightseeing tour is part of the program during your trip to Annapolis, stop by leading attractions like U.S. Naval Academy, Maryland State House and William Paca House. Check out Expedia's wide range of travel options and book your ideal vacation to Annapolis now.

Top Annapolis Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG
Element by Marriott Arundel Mills BWI Airport
Hotel Burg
Convention Center PH Free indoor parking
DoubleTree Hotel Baltimore - BWI Airport

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis

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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 CA $128 per night from Jul 19 to Jul 20
CA $128
CA $195 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (1,888 reviews)
"Other than the very comfortable beds, the best thing about our stay here is the location. It's an easy 10 minutes walk to the wharf, market space, USNA, state capital, etc. The rooms were very clean and the valet staff was super fast."

Reviewed on Jul 8, 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 CA $146 per night from Jul 12 to Jul 13
CA $146
CA $167 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,028 reviews)
"We had an average stay. The hotel itself is a bit dated - needs renovation and updates. Our room had an odor - like mildew. The front desk staff is underwhelming. Lacked energy and friendliness and didn't want to be bothered honestly. However, the wait staff at breakfast in the restaurant were great. ..."

Reviewed on Jul 8, 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 refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 15 to Jul 16
CA $167
CA $190 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"From the moment we walked in, to an empty reception, and empty bar area we were not impressed. after several minutes, an unsmiling, unwelcoming receptionist came out of the side office and instead of coming over to us, stood at the opposite end of the reception and asked if she could help, with no ..."

Reviewed on Jul 8, 2026

Crowne Plaza Annapolis by IHG
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

What to do in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $957 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 many days is enough for Annapolis?
To get the most out of an Annapolis vacation, we suggest booking for 2 days. Split your time between discovering Annapolis City Dock, Westfield Annapolis Mall and other well-known attractions, as well as experiencing neighbourhoods like Parole and Historic District. If you've got some time to spare, include a day trip or tour in your Annapolis vacation itinerary.
Is it worth booking a vacation package to Annapolis?
Whether you want to visit key attractions such as Annapolis City Dock and Westfield Annapolis Mall on your Annapolis vacation, or coming for its great history, culture and watersports, there's something for everyone here. With so much to see and do, you'll soon find out why so many visitors think Annapolis is a good vacation destination.
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.

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