Annapolis Vacations from $288

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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.

The Latest Annapolis vacation packages

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
Save 100% on your flight
Price was $508, price is now $288 per person
$288
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Nonsmoking room smells like pot

Reviewed on Aug 20, 2025

Tru By Hilton Baltimore Harbor East, MD

Tru By Hilton Baltimore Harbor East, MD

2.5 out of 5
Little Italy
Save 100% on your flight
Price was $600, price is now $366 per person
$366
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,006 reviews)
Great location for Little Italy

Reviewed on Aug 22, 2025

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
Save 100% on your flight
Price was $1,149, price is now $711 per person
$711
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,007 reviews)
Very convenient for an Orioles game!

Reviewed on Aug 20, 2025

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

4.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $599, price is now $397 per person
$397
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (102 reviews)
This hotel is amazing. Very friendly, in a great location, and had no problems. My dog came with me and they did not give me a hard time or make me feel judged like other hotels have. Great walking distance, had complimentary wine hour and tea/coffee. 10/10 stay all around. We will be returning upon ventures in Bmore area!

Reviewed on Aug 18, 2025

Holiday Inn Express Hunt Valley by IHG

Holiday Inn Express Hunt Valley by IHG

2.5 out of 5
Save 100% on your flight
Price was $543, price is now $363 per person
$363
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
This hotel was ok. Most of the staff was friendly and the hotel was in a convenient location.

Reviewed on Aug 19, 2025

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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

1 out of top 10 points of interest in this area
5/5(83 area reviews)

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

Discover the most popular places to visit in Annapolis

U.S. Naval Academy which includes 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

$80
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

$26
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

$40
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Annapolis

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
$143 nightly
The price is $163 total per night from Sep 8 to Sep 9
$163 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,836 reviews)
"There were no ghosts!"

Reviewed on Aug 20, 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
$161 nightly
The price is $183 total per night from Sep 2 to Sep 3
$183 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
"Very good"

Reviewed on Aug 20, 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
$101 nightly
The price is $115 total per night from Sep 1 to Sep 2
$115 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"It was good."

Reviewed on Aug 19, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 582 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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Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination from $288 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?
January, October and December are the best times to search for cheap Annapolis vacation packages. Opting to travel in quieter months means you can typically find lower prices on accommodations and flights.
How many days is enough for Annapolis?
With around 2 days, you'll have enough time to experience popular neighborhoods such as Parole and Historic District during your Annapolis vacation. Be sure to also add Bay Ridge Beach and Annapolis Bowl to your must-do list. Looking for more adventures? Consider exploring outside of Annapolis on day trips and tours.
Is it worth booking a vacation package to Annapolis?
Well known for its culture, watersports and festivals, an Annapolis vacation is a hit with all kinds of travelers. Be sure to check out leading sights like William Paca House and Navy-Marine Corps Memorial Stadium, and consider renting a car for day trips to experience 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 best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Annapolis.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will likely be the biggest expense during your trip to Annapolis.
  3. Explore Annapolis using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Annapolis. You can also save your favorite places, collaborate with family and friends and manage your plans in one place.
  4. Decide how long to go away for: Now that you're more familiar with Annapolis, you can work out the right length of your break. Pull together a rough plan and allocate enough time to cover everything you want to see.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose an Annapolis vacation package that brings all your bookings together.
  6. Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Browse some of the incredible things to do in Annapolis and reserve your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Annapolis vacation packages?
Set off on your dream getaway to Annapolis with help from our Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.