Annapolis Vacations from ¥394,688

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Darcy Hotel

The Darcy Hotel

Downtown Washington D.C.
¥394,688
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.2/10 Wonderful! (1,716 reviews)
Lyle Washington D.C.

Lyle Washington D.C.

Northwest
¥431,064
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.4/10 Exceptional! (1,645 reviews)
Bed comfortable. Brighter room than most nearby hotels. Restaurant very good but very noisy while we were there. Young people seem to be the dominant group.

Reviewed on Oct 9, 2026

Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

Northwest
¥405,280
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
8.8/10 Excellent! (3,282 reviews)
The River Inn

The River Inn

Northwest
¥411,725
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9.4/10 Exceptional! (2,157 reviews)
Excellent service and comfortable atmosphere Great location

Reviewed on Oct 9, 2026

Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.
¥410,340
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Baltimore (BWI)
9/10 Wonderful! (2,093 reviews)

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

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.

A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Spa Creek and Ballet Theater of Maryland.

A grassy area with two Adirondack chairs near a waterfront, a large tree, and a distant view of the sea.

Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

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Admiral Heights

Admiral Heights might not have many top sights, but Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts are two attractions nearby that you can check out.

Find the Best Annapolis Vacation Packages

Things to do in and around Annapolis

Shopping

For a delightful shopping experience in Annapolis, visit Westfield Annapolis Mall, which offers a vibrant mix of business and entertainment. If you're up for a drive, head to Marlborough Village Center, located 29.0km away, for a charming family-friendly atmosphere. Don't miss the Wild Bird Center for unique gifts.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere for sports enthusiasts looking to engage in recreational activities. Nearby, Bay Hills Golf Club provides a tranquil outdoor golfing experience, perfect for relaxation. Meanwhile, the Ballet Theater of Maryland invites you to immerse yourself in cultural performances, combining entertainment with a touch of romance.

Adventure

Experience thrilling fun at Annapolis Bowl, an arcadeAdventureZone brimming with family-friendly games. Dive into the excitement at Annapolis Sailing School, where you can master water sports amidst beautiful scenery. For tennis enthusiasts, Tose Family Tennis Center offers a vibrant atmosphere for adventurous play.

Nightlife

Annapolis offers a vibrant nightlife with charming bars and live music. Visit Rams Head Tavern for local bands and great food. For a relaxed vibe, check out The Federal House, where you can enjoy craft cocktails. Don't miss the scenic views along the waterfront while you explore.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Annapolis

Annapolis, Maryland, is perfect for family vacations and outdoor adventures, featuring urban parks, historic houses, and marinas. Visitors can enjoy a mix of culture and family experiences at local attractions such as the haunted sites of Annapolis, the scenic Annapolis Harbor, and the informative Annapolis Maritime Museum. Exploring historic Annapolis offers a glimpse into the city’s rich heritage, making it an ideal destination for all types of travelers.

  • U.S. Naval Academy: Immerse yourself in American naval history at the U.S. Naval Academy, where stunning architecture meets rich traditions. Explore the beautifully landscaped grounds, visit the Naval Academy Museum, and witness the impressive Chapel, making it a unique experience filled with historical significance.
  • Chesapeake Bay Bridge: Experience breathtaking views from the Chesapeake Bay Bridge, an engineering marvel that connects Maryland's eastern and western shores. Walk or drive across this iconic bridge to enjoy panoramic vistas of the Chesapeake Bay, an unforgettable urban experience.
  • Sandy Point State Park: Discover the natural beauty of Sandy Point State Park, a haven for outdoor enthusiasts. With picturesque beaches, hiking trails, and picnic areas, it's perfect for adventure seekers looking to relax and enjoy the scenery by the bay.

Best time to go to Annapolis

The best time to visit Annapolis is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnySlightly LowSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnySlightly LowSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyAverageSlightly High
June73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
July78.4°F (25.8°C)Light RainMostly SunnySlightly HighAverage
August76.8°F (24.9°C)Light RainMostly SunnySlightly HighAverage
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnySlightly HighAverage
November48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Annapolis

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Annapolis.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Annapolis.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Annapolis Hotel Deals

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
¥23,177
¥26,421 total
Oct 26 - Oct 27
includes taxes & fees
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
¥16,703
¥19,042 total
Oct 11 - Oct 12
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD
Fully refundable
¥18,316
¥20,881 total
Oct 18 - Oct 19
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"The only suggestion is there should be complimentary coffee in the lobby in the morning"

Reviewed on Oct 9, 2026

Crowne Plaza Annapolis by IHG
See all 557 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.

Stay near popular Annapolis attractions

A large suspension bridge over a body of water with a sandy beach in the foreground.

Chesapeake Bay Bridge

8.8/10 (1,066 reviews)
This 4.3-mile engineering marvel connects Maryland's shores while offering spectacular panoramic bay views. Drive across at sunrise to witness the Chesapeake's shimmering waters dotted with sailboats below.
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A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.

Sandy Point State Park

8.6/10 (221 reviews)
Sandy Point State Park offers pristine Chesapeake Bay beachfront beneath the towering Bay Bridge. Visitors can launch boats, fish for striped bass, or attend the renowned Maryland Seafood Festival.
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A town with historic buildings, a prominent church steeple, and a weather vane atop a building.

Maryland State House

9.0/10 (433 reviews)
Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.
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Navy-Marine Corps Memorial Stadium

9.2/10 (287 reviews)
Home to the Navy Midshipmen teams, this stadium honors naval service members with its impressive Memorial Plaza. Catch the vibrant atmosphere of a fall football game or the annual Annapolis Crab Feast in August.
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Maryland Renaissance Festival

10.0/10 (1 review)
Step back in time at this sprawling 16th-century English village recreation with over 200 performers. Watch jousting tournaments, sample period foods like turkey legs, and browse 140 artisan craft shops.
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Annapolis Mall Shopping Center

9.0/10 (23 reviews)
Annapolis Mall offers over 140 stores including Macy's and Nordstrom in a spacious, well-maintained environment. Visit weekday mornings for a relaxed shopping experience, then catch a film at the 11-screen AMC theater.
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Sandy Point Beach

9.6/10 (10 reviews)
Sandy Point State Park features a mile-long beach with Bay Bridge views on the Chesapeake. Enjoy swimming in calm waters, launch a boat from the marina, or experience the September Seafood Festival.
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Annapolis Harbor Center Shopping Center

9.2/10 (24 reviews)
This shopping hub features the Pennsylvania Dutch Farmers Market, offering fresh local produce and handcrafted goods. Browse unique shops, enjoy diverse dining options, or catch a film at the on-site theater.
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What to do in Annapolis

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

¥4,706
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

¥1,513
per traveler
80% of travellers recommend
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

¥4,079
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
See all activities in Annapolis

Frequently asked questions

How much does an Annapolis vacation package cost?
You can snap up a vacation package to this popular destination from ¥394,688 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?
You're likely to find lower prices and greater availability in January, February and March. Take a look at our cheap Annapolis vacation packages and you could land some excellent off-season deals.
How many days is enough for Annapolis?
Annapolis vacations come in various shapes and sizes, but to get a real feel for this destination, we think 2 days is a good ballpark. In this timeframe, you can visit major attractions like Bay Ridge Beach and Annapolis Bowl along with lesser-known gems. Don't forget to explore neighborhoods such as Parole and Historic District either. If you're smart with your time, you can even schedule a day trip from Annapolis too.
Is it worth booking a vacation package to Annapolis?
Popular for its history, culture and watersports, an Annapolis vacation has something for everyone. Be sure to check out main sights like Annapolis City Dock and Westfield Annapolis Mall, and consider renting some wheels for day trips to explore 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 perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Annapolis.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to put aside for your trip to Annapolis. Then, choose a property that matches your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to get to in Annapolis. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick an Annapolis vacation package that brings all your bookings together.

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