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.
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Price was CA $725, price is now CA $596 per person
CA $596
per person
Dec 1 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,007 reviews)

The Hotel at Arundel Preserve

The Hotel at Arundel Preserve

3.5 out of 5
Arundel Mills
Price was CA $1,249, price is now CA $1,020 per person
CA $1,020
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (2,009 reviews)

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Price was CA $1,160, price is now CA $964 per person
CA $964
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,134 reviews)
Lost my phone charger and went to buy one from the little hotel shop. They wanted $16 for a cheap wall plug that didn't even come with a cord.

Reviewed on Oct 29, 2026

The Quincy, an Ascend Collection Hotel

The Quincy, an Ascend Collection Hotel

2.5 out of 5
Downtown Washington D.C.
Price was CA $1,775, price is now CA $1,482 per person
CA $1,482
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (1,161 reviews)
the TV channels were lacking & didn't always work based on satellite connection... but other than that - great!

Reviewed on Oct 29, 2026

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Price was CA $1,582, price is now CA $1,325 per person
CA $1,325
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.8/10 Excellent! (1,185 reviews)
Room, although small, was very nice. Appeared to be a balcony w/no access. Shower was different but great water pressure. Nice river view. Great whiskey bar. Not thrilled w/our meal @ Kingbird. Will likely return in summer to utilize Top of the Gate.

Reviewed on Oct 27, 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 $139 per night from Nov 30 to Dec 1
CA $139
CA $206 total
Nov 30 - Dec 1
includes taxes & fees
Historic Inns of 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 CA $141 per night from Nov 10 to Nov 11
CA $141
CA $161 total
Nov 10 - Nov 11
includes taxes & fees
Crowne Plaza Annapolis by IHG
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 $125 per night from Nov 10 to Nov 11
CA $125
CA $142 total
Nov 10 - Nov 11
includes taxes & fees
8.8/10 Excellent! (1,263 reviews)
"The staff friendliness was the best part of this trip! My bed was just as terrific. The building has certainly been around for years, so some wear and tear visible, but the team made every effort to make sure I was taken care of. I can't recommend the staff enough."

Reviewed on Oct 29, 2026

DoubleTree by Hilton Hotel Annapolis
See all 557 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Annapolis attractions

A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".

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: Annapolis Harbor and U.S. Naval Academy Cruise

Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise

CA $48
per adult
90% of travellers recommend
Annapolis: Annapolis Harbor and U.S. Naval Academy Cruise
Annapolis Harbor and U.S. Naval Academy Cruise

Annapolis Harbor and U.S. Naval Academy Cruise

CA $48
per adult
Annapolis Harbor and U.S. Naval Academy Cruise
Scenic Spa Creek Cruise of Annapolis

Scenic Spa Creek Cruise of Annapolis

CA $48
per adult
Scenic Spa Creek Cruise of Annapolis
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $596 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.

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