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.
Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
per person
Apr. 2 - Apr. 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (654 reviews)
Second time staying here and look forward to staying here again.

Reviewed on Jan. 22, 2025

Atlantic Sands Hotel & Conference Center

Atlantic Sands Hotel & Conference Center

3.5 out of 5
North Rehoboth
per person
Mar. 15 - Mar. 22
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
8.4/10 Very Good! (1,325 reviews)
Clean and convenient

Reviewed on Jan. 21, 2025

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
per person
Mar. 28 - Apr. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very Good! (1,414 reviews)
Very close to Bwi and able to shuttle early for our flight. Nice having a bar as well on property

Reviewed on Jan. 21, 2025

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Mar. 28 - Apr. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.6/10 Excellent! (1,002 reviews)
The staff were amazing! From security to check in and out all dealings with staff exceeded expectations. Property was very clean! My only stay issues were not the hotel or the staffs issues. Loud room neighbors and parking prices were my only complaints. The prices were on par with the area so again not their fault at all.

Reviewed on Jan. 21, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
per person
Mar. 6 - Mar. 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Every thing is so beautiful

Reviewed on Jan. 19, 2025

Where to stay in Annapolis

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

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

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 $196 per night from Feb. 3 to Feb. 4
CA $196
CA $224 total
includes taxes & fees
Feb 3 - Feb 4
9.2/10 Wonderful! (1,004 reviews)
"Dog friendly"

Reviewed on Jan. 20, 2025

Graduate by Hilton 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 $145 per night from Feb. 9 to Feb. 10
CA $145
CA $165 total
includes taxes & fees
Feb 9 - Feb 10
8.4/10 Very Good! (1,001 reviews)
"amazing"

Reviewed on Jan. 7, 2025

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is CA $157 per night from Jan. 27 to Jan. 28
CA $157
CA $179 total
includes taxes & fees
Jan 27 - Jan 28
8.6/10 Excellent! (1,002 reviews)
Hotel is awesome but the noise is too much!
"I decided to give this hotel a second chance since I love its location and everything from the hotel but the noise is insane. The first time I stayed, kids were running up and down the hallway and knocking on doors and laughing at 6am. Then room service kept on hitting the vacuum on the walls and ..."

Reviewed on Jan. 13, 2025

Crowne Plaza Annapolis, an IHG Hotel
See all 564 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

Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination from CA $546 on Expedia. However, how much your vacation 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 vacation packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis vacations 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 neighborhoods 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 vacation package to Annapolis?
Popular for its history, culture and watersports, an Annapolis vacation 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 vacation as a package?
Expedia vacation 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 vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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, favorite 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 vacation package that brings all your bookings together.

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

4.5/5(8 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.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

4.5/5(2 reviews)

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

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

CA $56
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

CA $115
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Annapolis Ghost Tour: Phantoms of Annapolis

CA $49
per adult
Annapolis Ghost Tour: Phantoms of Annapolis
See all activities in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.