Annapolis Vacations from $335

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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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $483, price is now $335 per person
$335
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
The staff was outstanding—everyone from the front desk to the room cleaning & maintenance! The campus and environment was also very clean and outstanding. I’ll only stay at Kellogg on my visits to Washington DC!!

Reviewed on Nov 25, 2025

Kent Island Resort

Kent Island Resort

3.5 out of 5
Save 100% on your flight
Price was $567, price is now $356 per person
$356
per person
Jan 17 - Jan 21
found 16 hours ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
9.2/10 Wonderful! (124 reviews)
The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do.

Reviewed on Nov 15, 2025

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $1,187, price is now $804 per person
$804
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Miami (MIA) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
A lovely and comfortable hotel with pleasant staff! Would stay here again!

Reviewed on Dec 7, 2025

Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
Save 100% on your flight
Price was $997, price is now $696 per person
$696
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Baltimore (BWI)
8.4/10 Very Good! (462 reviews)
There was no shower curtain in my bathroom

Reviewed on Dec 8, 2025

Furnished Apartments

Furnished Apartments

3 out of 5
Ashton Heights
Save 100% on your flight
Price was $1,086, price is now $764 per person
$764
per person
Jan 14 - Jan 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
It was ok. Out of date appliances, could not adjust room temperature above 65 degrees. No outlet in bathroom to plug in hair dryer, peeling finish on bathroom fixtures. Clean though in a nice neighborhood.

Reviewed on Apr 23, 2023

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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

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 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

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
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
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

Costa Rica Rainforest Guided Tram Tour

AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó

$67
per adult
AERIAL TRAM TOUR - HALF DAY PASS Rainforest Adventures Jacó
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

$40
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Ashes and Apparitions of Annapolis Ghost Tour

$32
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
See all activities in Annapolis

Annapolis Hotel Deals

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
$76 nightly
The price is $87 total per night from Dec 28 to Dec 29
$87 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
Great

Reviewed on Dec 9, 2025

DoubleTree by Hilton Hotel 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
$164 nightly
The price is $187 total per night from Dec 16 to Dec 17
$187 total
Dec 16 - Dec 17
Total with taxes and fees
8.8/10 Excellent! (1,898 reviews)
Rooms are in the different buildings so we needed to check in to find out where we were staying. Parking is difficult so we chose to pay for valet. Loved the location and it was convenient for Midnight Madness shopping and to great restaurants.

Reviewed on Dec 6, 2025

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$97 nightly
The price is $111 total per night from Dec 15 to Dec 16
$111 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (1,017 reviews)
Mold on the fruit at Breakfast. Grapefruit dried out. Broken bathroom fixtures (toilet paper holder & magnifying mirror). No extra blanket in closet since husband and I like to sleep at different temperature. Moldy grout in bathroom.

Reviewed on Dec 2, 2025

Crowne Plaza Annapolis by IHG
See all 561 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.

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

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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 $335 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.

Explore a world of travel with Expedia

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