Annapolis Vacation Packages 2025/2026 from $364

Annapolis flight + hotel vacation packages

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Hampton Inn & Suites Annapolis

Save 100% on your flight

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Baltimore (BWI)

This hotel features a gym and a seasonal outdoor pool. Families will appreciate the arcade/game room and onsite laundry facilities. Guests will appreciate free perks like buffet breakfast and WiFi in public areas.

Historic Inns of Annapolis

Historic District

Save 100% on your flight

per person

Sep 4 - Sep 7

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to Baltimore (BWI)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.

Sagamore Pendry Baltimore

Fells Point

Save 100% on your flight

per person

Sep 5 - Sep 8

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Baltimore (BWI)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Graduate by Hilton Annapolis

Save 100% on your flight

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Budget Plaza Motel

Brooklyn

Save 100% on your flight

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Baltimore (BWI)

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.

Top Annapolis hotels deals

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

Free Cancellation

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This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.

Pet friendly

Free WiFi

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court, Annapolis, MD

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.

Pet friendly

Parking included

Hilton Garden Inn Annapolis Downtown

174 West Street, Annapolis, MD

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and dry cleaning are also offered.

Pet friendly

Free WiFi

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St, Annapolis, MD

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.

Pet friendly

Free WiFi

Best Western Annapolis

2520 Riva Rd, Annapolis, MD

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Country Inn & Suites by Radisson, Annapolis, MD

2600 Housley Road, Annapolis, MD

Free Cancellation

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This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

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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.

Popular places to visit

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.

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.

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.

Annapolis Vacations

Annapolis, Maryland is a city that full of historic homes, beautiful gardens, and impressive architecture. Go there to learn more about the history of the city, and by extension the United States, and indulge in the fine wines and delicious food along the way. Vacation packages in Annapolis through Travelocity make it possible to affordably visit this vibrant city while still saving some cash for souvenirs.

Major Attractions

After arriving at one of the hotels in Annapolis, drop off your bags and head straight for the walking tour of the Naval Academy. You will learn the history of the institution and see the impressive grounds. Visit St. Anne's Church, which was finished in 1704, and then walk over to the William Paca House and Garden. Paca, one of the signers of the Declaration of Independence, was Maryland's third governor. The grounds and home, built in the 1760s, play host to events throughout the year, and give you a real peek into life in the mid-18th century. Book one of the Annapolis rental cars available through Travelocity and drive down to see the Maryland World War II Memorial off of Ritchie Highway before wrapping up with a State House tour.

Recurring Festivals and Events

In November, history buffs rejoice at the annual Annapolis by Candlelight tour. Privately owned historic homes open their doors to you so that you can learn more about the cultural and architectural significance of the properties, as well as the city. If you are in town on one of the package deals to Annapolis for Mother's Day weekend, join the incredibly popular plant event inside the William Paca Garden, where you can learn about and buy hundreds of different varieties of plant life. Fourth of July celebrations bring you back to the Paca estate, where you can watch reenactments and speeches surrounding the signing of the Declaration of Independence.

Ready to set off for this intriguing East Coast city? Get mobile exclusive deals on vacations in Annapolis through the Travelocity app and start planning for your exciting Maryland escape.

Tours and Activities in Annapolis

Some getaway experiences can be so amazing that they utterly bowl us over. They become precious moments to recount for years to come. Are you ready to create some outstanding new memories?

Traveling to Annapolis? Snap up an a Small-Group Original Annapolis Seafood Crawl or a Small-Group Explore the Heart of Annapolis Tour while you're over there — they'll be among the highlights of your trip!

Frequently asked questions

How much are vacation packages to Annapolis?

With vacation packages available from just $364, it's not necessary to wipe out your bank balance for your visit to Annapolis. Travelocity can help. Bundle flights, hotels and tours into a convenient package and land serious discounts. The more you book, the more you save.

How long should my Annapolis vacation be?

If you're looking for some guidance, most visitors spend about 2 nights in Annapolis. But to discover the true essence of this destination, stay a few extra nights. That way you can cross off more attractions and really take in the local culture.

Where can I get the best vacation package deals for Annapolis?

It's hard to top Travelocity when it comes to putting together your Annapolis package deal. There are at least 400 air carriers and 1,000,000 worldwide properties to choose from. Secure your trip now and get ready to cross another exciting destination off your list.

Why should I purchase my Annapolis vacation bundle with Travelocity?

You'll not only save loads, but you can also access our 24/7 customer support, top-notch service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover hidden gems and forge long-lasting memories --- we'll take care of the little details.

Can I save money on my Annapolis car rental if I combine it with a hotel or flight?

With an Annapolis vacation package, you can bundle your hotel, flight and car bookings and save tons. If you can't wait to see the best of this exciting destination, why not make tracks to Liberty Bell Center? This famous attraction is 100 mi from Annapolis. With a rental car, you'll be there belong long.

Which airport is best for Annapolis?

Ronald Reagan Washington National Airport (DCA) is popular. It's located approximately 30 mi west of Annapolis. Other options worth considering are Washington Dulles Intl. Airport (IAD) (50 mi away from central Annapolis) and Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (17 mi away from central Annapolis).

What is there to do in Annapolis?

You'll sense an undeniable magic as you stroll through the streets of Annapolis. U.S. Naval Academy and Chesapeake Bay Bridge are just two landmarks that make this city so popular, so put them at the top of your to-do list.

Where should I stay when visiting Annapolis?

Many people choose to spend their nights at the Historic Inns of Annapolis. It's sure to be a great base for your Annapolis escape.

Where to stay in Annapolis: Best areas for travelers

Historic District: Full of ambiance and atmosphere, this is a perfect match if you love being in the heart of the action. Select a room at the Historic Inns of Annapolis, the Historic District - 1 Block to Naval Academy & State House or the Historic Downtown Annapolis Home for Rent- Steps to Naval Academy. Then, you'll be well positioned to explore this neighborhood's biggest attractions, like Maryland State House and William Paca House.
Parole: Attractions like Annapolis Bowl make this an enticing area for families. Once the kids have had their fun, spend your nights in a comfortable hotel like the Country Inn & Suites by Radisson, Annapolis, MD or the Red Roof Inn Annapolis. Need more options? The DoubleTree by Hilton Hotel Annapolis is another place to sleep off all those adventures.
Stevensville: If you're looking for someplace to stay in this neighborhood, check out the rates at the Perfect Getaway, Waterfront Townhouse on Chesepeake Bay, Kent Island, Maryland and The Waterfront Historic Kent Manor Inn. Whichever one you choose, you'll be in a good position to venture out and explore the local sights.