Annapolis Vacations from $303

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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.
Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Mount Vernon
Price was $416, price is now $303 per person
$303
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,000 reviews)
I had such a great experience during my stay! The hotel was clean, comfortable, and conveniently located, but what truly made it special was the incredible customer service. Tyjuan checked us in and went above and beyond to make sure we were taken care of the entire time. He was friendly, professional, and genuinely helpful — from check-in to checkout. It’s rare to come across someone who clearly takes pride in what they do, and his positive attitude made a big difference in our trip. Thank you, Tyjuan, and the rest of the team for making our stay so pleasant — we’ll definitely be back!

Reviewed on Oct 20, 2025

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
Price was $919, price is now $580 per person
$580
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,004 reviews)
Such a beautiful hotel in a great location. No lack of bars or restaurants in Fells Point.

Reviewed on Oct 13, 2025

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 out of 5
Nottingham
Save 100% on your flight
Price was $589, price is now $429 per person
$429
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
7.8/10 Good! (1,008 reviews)
It was exactly what I wanted.

Reviewed on Oct 12, 2025

DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
Price was $464, price is now $338 per person
$338
per person
Dec 25 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (1,004 reviews)
Very Clean & Comfortable

Reviewed on Oct 21, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Price was $411, price is now $306 per person
$306
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (786 reviews)
This place was amazing

Reviewed on Oct 22, 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

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
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
$145 nightly
The price is $166 total per night from Nov 2 to Nov 3
$166 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,868 reviews)
Loved everything. Perfect location right on the main drag

Reviewed on Oct 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
$150 nightly
The price is $171 total per night from Nov 23 to Nov 24
$171 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,015 reviews)
Family wedding
Wonderfully. We were pleasantly surprised at the hotel. Very nice. Well decorated. Convenient and walkable location.

Reviewed on Oct 20, 2025

Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
$100 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
The room was very clean but the mattress not so great. I found hair on the sheets

Reviewed on Oct 15, 2025

Crowne Plaza Annapolis by IHG
See all 585 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 $303 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.