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

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,365, price is now CA $957 per person
CA $957
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,002 reviews)
The property is very nice unfortunately the night staff need to be more helpful when we reported things missing in the room like towels no one came up I call twice to the front desk to then be told I had to go down and get it my self other wise nice place to stay

Reviewed on Jul 7, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,630, price is now CA $1,068 per person
CA $1,068
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,003 reviews)
Didn’t like that room service wasn’t available during my visit. Other than that the location was perfect!

Reviewed on Jul 5, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,096, price is now CA $1,403 per person
CA $1,403
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (81 reviews)
Excellent stay in a quiet area, but still plenty to do

Reviewed on Jul 8, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,567, price is now CA $1,082 per person
CA $1,082
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was CA $1,397, price is now CA $993 per person
CA $993
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,176 reviews)
All was good. The hotel has been around for a good number of years, but it still is a pleasant place to stay.

Reviewed on Jul 7, 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

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

Ready to book your vacation to 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
See all 560 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.
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All Inclusive Vacations
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Stay near popular Annapolis attractions

A grand hall with ornate columns, a large staircase, and flags.

U.S. Naval Academy

9.4/10 (1,474 reviews)
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.
See properties

What to do in Annapolis

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

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

CA $14
per traveller
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Historic Annapolis Food Tour

Historic Annapolis Food Tour

CA $113
per adult
Historic Annapolis Food Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

CA $45
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
See all activities 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.

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.