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Annapolis Vacation Packages

Choose two or more items and save on your trip:

Annapolis Vacation: Coronavirus Information

Most Annapolis hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Annapolis trip, please visit our Coronavirus Information page (opens in new window).

Top Annapolis Flight + Hotel Deals

Hotel Zena
The Ritz-Carlton, Tysons Corner
Tysons Corner Marriott
The Watergate Hotel
The Westin Washington Dulles Airport
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2021 Annapolis vacation deals

Thompson Washington D.C.
Morrison House Old Town Alexandria, Autograph Collection
Sheraton Baltimore North Hotel
Hyatt Regency Bethesda
Hilton Baltimore Inner Harbor
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See all available trips from Ashburn to Annapolis

Top Hotels in Annapolis

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $85 per night from Nov 1 to Nov 2
4.5/5Wonderful! (937 reviews)

"Loved the Inn! Room very nice and staff super friendly!"…"

Reviewed on Oct 15, 2020

Historic Inns of Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $110 per night from Oct 22 to Oct 23
4.3/5Excellent! (836 reviews)

"Staff very helpful and professional; very clean; enjoyed convenience of Starbucks"…"

Reviewed on Oct 18, 2020

The Westin Annapolis
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
3.5 out of 5
210 Holiday Court, Annapolis, MD
Free CancellationReserve now, pay when you stay
The price is $88 per night from Nov 3 to Nov 4
4.2/5Very Good! (972 reviews)

"I always stay at this Doubletree whenever I am in MD. It’s super clean and usually very quiet. Unfortunately this trip I was placed in a room by the highway and on my second night a huge multi room family came in and proceeded to slam doors and scream to the top of their lungs back and forth to communicate ..."…"

Reviewed on Sep 27, 2020

DoubleTree by Hilton Hotel 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.

Top things to do in Annapolis

Historic Annapolis Food Tour
Image for Historic Annapolis Food Tour

Historic Annapolis Food Tour

Per adult
100% of travellers recommend
Annapolis Scavenger Hunt: Red Bricks & Blue Views
Image for Annapolis Scavenger Hunt: Red Bricks & Blue Views

Annapolis Scavenger Hunt: Red Bricks & Blue Views

Per adult
DC Hop On-Off Tour + Arlington Cemetery Tour + Water Taxi
Image for DC Hop On-Off Tour + Arlington Cemetery Tour + Water Taxi

DC Hop On-Off Tour + Arlington Cemetery Tour + Water Taxi

Per adult
86% of travellers recommend

What are the advantages of a road trip to Annapolis?

There’s nothing quite like a Annapolis road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Annapolis or bundle your hotels with car rentals to save even more. With our Annapolis packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Annapolis?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Annapolis and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Annapolis?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Annapolis. You can book all the road trip activities on your Annapolis wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Annapolis. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does an Annapolis vacation package cost?
We make it simple to travel somewhere new, with Annapolis packages starting from as low as $257. You’ll have the flexibility to bundle your favorite airlines, hotels and car rental. For the ultimate escape, why not add some tours and activities to your itinerary?
If I'm not able to travel, can I cancel my Annapolis vacation package?
You sure can, and we’ll help you every step of the way. You may be able to amend or cancel your Annapolis vacation package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances suddenly change, take a look at our Customer Service Portal for more information.
How do I get a cheap travel package to Annapolis?
Booking an Annapolis vacation package with Expedia is a great way to save. Lock in your trip now and you can save up to $583 — it’s really that easy! We offer access to over 550 partner airlines and 1,000,000 properties globally. With such an awesome range to choose from, you’ll have no issues pulling together your perfect escape.
Where should I stay in Annapolis?
An escape to Annapolis isn’t complete without taking in the atmosphere in Historic District, so why not secure a hotel room in this happening neighborhood? That way, you’ll be just moments from Maryland State House. If Six Flags America is on your must-see list, stay in the Bowie area.
What are the top hotels in Annapolis?
Crowne Plaza Annapolis and Best Western Annapolis are both sought-after options in the neighborhood of Parole. If you’d rather stay in the Historic District area, consider locking in a room at Historic Inns of Annapolis or Annapolis Waterfront Hotel, Autograph Collection.
When is the best time of year to visit Annapolis?
Anytime is an excellent time of the year to vacation in Annapolis, but you’ll generally pick up the best deals in . Prices tend to increase in , so expect to pay top dollar for your flights and hotel. Love sightseeing but don’t like huge crowds? Lock in your Annapolis escape for . Typically, it’s much quieter than in .
How far in advance should I book my Annapolis vacation?
To bag cheap prices, book as soon as you can. Airlines typically start selling tickets, along with some of the lowest fares, up to a year ahead of time. Hotels, car rental and experiences should also be booked well in advance so you can have the pick of the bunch. If you’ve decided on a last-minute getaway to Annapolis, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Annapolis travel package include?
That depends on what you’re after. If you’re traveling solo, you might decide to combine hotels and flights. Taking the whole crew to Annapolis? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking an Annapolis travel package?
Locking in all the parts of your trip together is a terrific way to save. Combine your car rentals, airfares and hotels into a tidy little package. But your options don’t end at hotels. Expedia offers all sorts of properties, including vacation rentals like beach villas and spacious residences. The list goes on!
Does Expedia offer Book Now, Pay Later Annapolis vacation packages?
If you’re eager to see the world but aren’t able to pay full price, Expedia can help with an easy payment plan. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your vacation today.
Can I choose my airline with an Annapolis Expedia vacation package?
Yes, of course. We have more than 550 airline partners globally, so go with the carrier that best fits your travel needs.