Annapolis Vacations

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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.

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
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 hotel + flight trips in Historic District

Find the Best Annapolis Vacation Packages

Annapolis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
39,500
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

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 $159 per night from Nov 24 to Nov 25
$159
includes taxes & fees
$139 per night
Nov 24 - Nov 25
9.2/10 Wonderful! (1,001 reviews)
"Great property! Has easy parking and everything is within walkable distance, 5 min. Would definitely return!"

Reviewed on Oct 22, 2024

Graduate by Hilton Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is $167 per night from Nov 24 to Nov 25
$167
includes taxes & fees
$127 per night
Nov 24 - Nov 25
8.8/10 Excellent! (1,676 reviews)
Lovely historic inn
"Place was historic and lovely. Comfortable room. Felt some updating is needed though - in room coffee machine hardly worked, bathroom grout needed cleaning. Noisy hallway. Received no housekeeping services while there unless asked for it."

Reviewed on Oct 28, 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 $115 per night from Nov 25 to Nov 26
$115
includes taxes & fees
$101 per night
Nov 25 - Nov 26
8.6/10 Excellent! (1,008 reviews)
Enjoyed
"The stay was good"

Reviewed on Oct 26, 2024

Crowne Plaza Annapolis, an IHG Hotel
See all 549 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination 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?
Use Expedia’s handy filters to help you find some fabulous Annapolis package deals. When you start your search, just set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your break for midweek, or look for Annapolis package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
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 vacation, browse our last-minute deals that can be booked up to a week before you go. Don’t want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Annapolis?

  1. Pick your dates: The things you’d like to do in Annapolis and your favorite season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Annapolis.
  3. Discover Annapolis with Expedia’s trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Annapolis. You can also save your must-visit places, collaborate with your group and organize your plans in one place.
  4. Decide how long to go away for: Now that you’re up to speed on Annapolis, you can figure out the right length of your vacation. Put together a rough itinerary and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Annapolis vacation package.
  6. Book activities and experiences in advance: Whether it’s entrance to a big attraction or a day trip in nature, you won’t have to worry about missing out on the highlights of Annapolis. Find all the incredible things to do in Annapolis in Annapolis with our dedicated activity guide.

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.

Discover the most popular places to visit in Annapolis

Image for U.S. Naval Academy

U.S. Naval Academy

4.5/5(446 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
Image for Chesapeake Bay Bridge

Chesapeake Bay Bridge

4/5(270 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
Image for Sandy Point State Park

Sandy Point State Park

4.5/5(13 reviews)

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

Image for Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

$28
Per adult
Annapolis: Crabtown Boos and Booze Haunted Pub Crawl
Image for Historic Annapolis Food Tour

Historic Annapolis Food Tour

$76
Per adult
Historic Annapolis Food Tour
Image for Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

$25
Per adult
Phantoms of Annapolis Ghost Tour By US Ghost Adventures
See all activities in Annapolis

Other vacations you might like

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