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.
DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
I really enjoyed my stay. Staff was excellent. It was quite and very comfortable

Reviewed on Jul. 27, 2025

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (910 reviews)
The site was very clean and comfortable

Reviewed on Aug. 3, 2025

Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
Great hotel & friendly staff. Clean & comfortable bed.

Reviewed on Aug. 7, 2025

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

4.5 out of 5
Downtown Baltimore
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (93 reviews)
I love the feel of this hotel. The valet and security staff were amazing.

Reviewed on Aug. 3, 2025

Hilton Garden Inn BWI Airport

Hilton Garden Inn BWI Airport

3 out of 5
per person
Oct 8 - Oct 12
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very Good! (1,002 reviews)
We had a great stay and the staff were amazing. The strong smell of chlorine however was all throughout the hotel and was nauseating. The pool was out of order so this may have been why it was so pungent. I believe it to be a one off kind of thing.

Reviewed on Aug. 4, 2025

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
Annapolis showing street scenes and a city as well as a small group of people

Historic District

1 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 $140 per night from Aug 17 to Aug 18
CA $140
CA $207 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,813 reviews)
"The close proximity to the town was great and convenient."

Reviewed on Aug. 6, 2025

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 CA $213 per night from Aug 17 to Aug 18
CA $213
CA $243 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."

Reviewed on Aug. 7, 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is CA $133 per night from Aug 17 to Aug 18
CA $133
CA $152 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Ashley at the main desk was very helpful and pleasant."

Reviewed on Aug. 5, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 583 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
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Discover the most popular places to visit in Annapolis

U.S. Naval Academy featuring military items, interior views and heritage architecture

U.S. Naval Academy

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.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Sandy Point State Park

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Sandy Point State Park

What to do in Annapolis

Food Tour Plate

Historic Annapolis Food Tour

CA $109
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

CA $36
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $41
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You'll find cheap prices from CA $592 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.