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.
Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
per person
Jan. 17 - Jan. 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Stayed a few times never had any issues

Reviewed on Nov. 11, 2024

Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Jan. 17 - Jan. 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,001 reviews)
The hotel was clean, and everybody working was very friendly and helpful. The continental breakfast was so good, and I loved that they had coffee and tea out throughout the day. This was a great experience!

Reviewed on Nov. 16, 2024

Hampton Inn Towson Downtown

Hampton Inn Towson Downtown

2.5 out of 5
per person
Jan. 17 - Jan. 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (304 reviews)
This was my first time staying at a Hampton Inn and at this location (Towson,MD). The front desk ladies were very pleasant and helpful and made my check-in a breeze(thank you). Also, though I didn’t use the valet service, the young men were very professional and helpful as well! I booked a “corner” king bed room Saturday through Monday and the cleanliness was impeccable! Shout out to housekeeping!! I really enjoyed my stay. Plenty of places to eat/ shop in the area.. many in walking distance… I did notice their is a “younger” crowd that frequents the common areas surrounding the hotel, but that’s not unusual being as though it’s next to a mall. The only characteristic about this hotel that I didn’t like was the off site parking garage Which is about a 5 minute walk to your vehicle..that’s Also an extra cost. I usually stay at hotels where the garage or lot is attached to the hotel or part of the grounds. But other than that I would definitely recommend this place. And if in the area I’ll be staying again!

Reviewed on Nov. 9, 2024

Holiday Inn Columbia East-Jessup, an IHG Hotel

Holiday Inn Columbia East-Jessup, an IHG Hotel

3 out of 5
per person
Jan. 17 - Jan. 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (845 reviews)
Parking is not really safe. There was a car that got their tires stolen. They need a security

Reviewed on Nov. 10, 2024

The Inn at Henderson's Wharf, Ascend Hotel Collection

The Inn at Henderson's Wharf, Ascend Hotel Collection

3 out of 5
Fells Point
per person
Jan. 17 - Jan. 22
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (607 reviews)
The staff was very friendly and helpful.

Reviewed on Nov. 16, 2024

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 hotel + flight trips in Historic District

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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 $192 per night from Nov. 24 to Nov. 25
CA $192
CA $219 total
includes taxes & fees
Nov 24 - Nov 25
9.2/10 Wonderful! (1,000 reviews)
"Very smooth checkin. The property is in a great location and is very clean."

Reviewed on Nov. 3, 2024

Graduate by Hilton Annapolis
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 $178 per night from Nov. 24 to Nov. 25
CA $178
CA $250 total
includes taxes & fees
Nov 24 - Nov 25
8.8/10 Excellent! (1,694 reviews)
Great stay in downtown Annapolis
"Outstanding stay! Both buildings (had to move halfway through due to construction) were comfortable and well cared for. Staff were very pleasant and easy to work with."

Reviewed on Nov. 14, 2024

Historic Inns of 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 $161 per night from Dec. 4 to Dec. 5
CA $161
CA $183 total
includes taxes & fees
Dec 4 - Dec 5
8.6/10 Excellent! (1,002 reviews)
"I had a relaxing and enjoyable stay. The breakfast was delicious."

Reviewed on Nov. 15, 2024

Crowne Plaza Annapolis, an IHG Hotel
See all 552 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?
From just CA $761. Yes, you read that correctly. Our Annapolis vacation packages are a great way to make your budget last longer. Bundle your favorite flights, hotels and rental car and get out and see this fabulous destination.
How do I get a cheap travel package to Annapolis?
Lock in flights that fit in with your schedule, add a hotel room to your booking and see how much you save with an Annapolis vacation package. It’s that simple! From hotels and flights to rental cars and activities, Expedia makes traveling cheap and easy. And with over 550 airlines and 1,000,000 hotel options globally to pick from, you’ll never be short of choice.
Where should I stay in Annapolis?
An escape to Annapolis isn’t complete without spending some time in Historic District, so why not get a hotel in this popular neighborhood? That way, you’ll be handy to Maryland State House. If U.S. Naval Academy is high on your to-do list, stay in Naval Academy.
What are the top hotels in Annapolis?
Travelers journeying to Annapolis often stay in Historic District. Graduate Annapolis and Historic Inns of Annapolis are well-known options in this neighborhood. But it’s not the only happening place around town! Eastport is another fantastic area and where you’ll find Crowne Plaza Annapolis, an IHG Hotel and DoubleTree by Hilton Hotel Annapolis.
How far in advance should I book my Annapolis vacation?
While not all air carriers release tickets early, it’s usually possible to start comparing international fares on Expedia up to 12 months in advance. This is the time when you’ll nab some fantastic deals. If you’re booking last minute, there’s a chance you could get lucky. Low prices occasionally become available a few weeks prior to departure.
What does an Expedia Annapolis travel package include?
Flights, rental cars and hotels, or any combination of the three — you decide! Whether you’re venturing to Annapolis on a family road trip or enjoying a solo break, there’s a package to fit your budget and style. Once you’ve made your booking, why not add on one or two activities?
What should I know before booking an Annapolis travel package?
Our prices are always low. However, you’ll grab even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and tons of choice.
Can I choose my airline with an Annapolis Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to select from globally. With so much choice, finding the perfect carrier to get you to Annapolis will be a cinch.
If I'm not able to travel, can I cancel my Annapolis vacation package?
It’s hard to predict what tomorrow might bring, so it’s good to know that you can cancel or change your Annapolis vacation package. If you booked in the last 24 hours, you may be eligible for a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

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: Crabtown Boos and Booze Haunted Pub Crawl

CA $39
Per adult
Annapolis: Crabtown Boos and Booze Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

CA $106
Per adult
Historic Annapolis Food Tour
Phantoms of Annapolis Ghost Walking Tour

Phantoms of Annapolis Ghost Walking Tour

CA $36
Per adult
Phantoms of Annapolis Ghost Walking Tour
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.