Annapolis Vacations from ¥338,656

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The Latest Annapolis Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Baltimore North - Pikesville
Pendry Baltimore
Live! Casino & Hotel Maryland
Sheraton Baltimore North Hotel
The Ivy Hotel

Where to stay in Annapolis

Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis

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

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
The price is ¥17,429 per night from Jun 8 to Jun 9
¥17,429
¥25,317 total
Jun 8 - Jun 9
includes taxes & fees
9/10 Wonderful! (1,850 reviews)
"Great hotel..will definitely be back"

Reviewed on May 29, 2026

Historic Inns of Annapolis
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
The price is ¥18,316 per night from May 31 to Jun 1
¥18,316
¥20,880 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"This property is old and they are working on improving it; however, we paid a premium price for a good brand that was not up to the standards of its name. We will not be staying there again."

Reviewed on May 28, 2026

DoubleTree by Hilton Hotel Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ¥44,436 per night from Jun 4 to Jun 5
¥44,436
¥50,657 total
Jun 4 - Jun 5
includes taxes & fees
8.8/10 Excellent! (931 reviews)
"Valet was full had to park garage pretty far away as well as a poor check in experience"

Reviewed on May 29, 2026

Annapolis Waterfront Hotel, Autograph Collection
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.