Annapolis Holidays from £1,063

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Your Annapolis Holiday

When you book a holiday package to Annapolis, you can relax and enjoy your getaway knowing your travel plans have been made in advance. Uncover the many gems of this city while staying in a neighbourhood like Historic District, which is great for history. Every trip to Annapolis needs a well-planned itinerary. Fill yours with famous sights like U.S. Naval Academy, Maryland State House and William Paca House. Stop dreaming and start travelling. Check out the range of options on Expedia today and put your Annapolis holiday plans into action!

The Latest Annapolis Holiday Deals

Prices and availability subject to change. Additional terms may apply.
Comfort Inn College Park North

Comfort Inn College Park North

2.5 out of 5
per person
15 Jul - 18 Jul
Return flight included
London (LON) to Baltimore (BWI)
7/10 Good! (942 reviews)
I liked everything about the property and all the people on the property were great

Reviewed on 16 Apr 2024

Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

2 out of 5
North Laurel
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Baltimore (BWI)
7/10 Good! (1,003 reviews)
Property had some age. One part has the doors inside and one part has the doors outside. Checked in after 10 pm due to traveling it was easy and simple.

Reviewed on 13 Apr 2024

Super 8 by Wyndham Laurel

Super 8 by Wyndham Laurel

2 out of 5
North Laurel
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Baltimore (BWI)
6.8/10 (650 reviews)
There was no breakfast; only coffee, orange jus and a cinnamon roll.

Reviewed on 1 Apr 2024

Holiday Inn Columbia East-Jessup, an IHG Hotel

Holiday Inn Columbia East-Jessup, an IHG Hotel

3 out of 5
per person
15 Jul - 18 Jul
Return flight included
London (LON) to Baltimore (BWI)
8.6/10 Excellent! (760 reviews)
The webpage said they have a shuttle to BWI airport and is not true.

Reviewed on 13 Mar 2024

Fairfield Inn By Marriott Laurel

Fairfield Inn By Marriott Laurel

2.5 out of 5
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Baltimore (BWI)
8.4/10 Very Good! (810 reviews)
Friendly staff and the breakfast offered lots of tasty choices.

Reviewed on 24 Apr 2024

Americas Best Value Inn Laurel

Americas Best Value Inn Laurel

2.5 out of 5
North Laurel
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Baltimore (BWI)
6.8/10 (139 reviews)
Easy check in easy check out.. I over sleep each morning so I never got to see what the breakfast options were but that’s on me. Overall nice stay.

Reviewed on 16 Mar 2024

Annapolis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
39,500
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

Our guide on where to stay in Annapolis

Check out a few of the areas and neighbourhoods we love in Annapolis Learn more about Annapolis
Annapolis featuring a city and street scenes as well as a small group of people

Historic District

2 out of top 10 points of interest in this area

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

Find hotels in Historic District

Our pick of the best Annapolis Hotel Deals

DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4 out of 5
210 Holiday Court, Annapolis, MD
Stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking and breakfast. Our guests praise the restaurant and the helpful staff in their ...
8.6/10 Excellent! (999 reviews)
Nice hotel
"One night stay while on our way north. Very clean, comfortable! Just what we needed! Great restaurant in the hotel!!"

Reviewed on 15 Apr 2024

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Stay at this historic hotel in Annapolis. Enjoy free WiFi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,603 reviews)
"Lovely historic Inn, excellent help, excellent valet."

Reviewed on 24 Apr 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast and a 24-hour fitness centre. Our guests praise the restaurant and the bar in their ...
9.2/10 Wonderful! (1,065 reviews)
"Complementary Valet parking"

Reviewed on 23 Apr 2024

Graduate Annapolis
See all 553 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Annapolis holiday with Expedia?
With top-value airfares, car hire and hotel options all in one convenient place, Expedia makes arranging your Annapolis break hassle-free. Moreover, we can help you bundle your bookings into a package holiday so you can save even more. Choose from fantastic properties, add flights and/or a car hire (and maybe also some exciting activities!) and land unbeatable prices. Need to change plans? Expedia offers a flexible cancellation policy for many bookings. To learn more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Annapolis?
Annapolis is busy in March, July and August, so if you want to steer clear of the crowds, visit in January, October and December. To give you an idea of what type of weather to expect, the daytime average temperature in January, the coolest month in Annapolis, is 1ºC. The warmest period here is July, when temperatures hit an average of 25ºC.
What are the top hotels for my holiday in Annapolis?
If you’d like to stay in the Historic District neighbourhood, Hilton Garden Inn Annapolis Downtown and Graduate Annapolis are in-demand options. Eastport is another well-known Annapolis area. We recommend Historic Inns of Annapolis or Crowne Plaza Annapolis, an IHG Hotel if you choose this end of town.
How do I get a cheap holiday to Annapolis?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you a few pounds too. An Annapolis holiday makes it simple to organise the perfect trip. With more than 400 airlines across the world to pick from, finding flights that fit your busy schedule won’t be an issue. In addition to that, we’ve got over 321,000 properties globally to choose from. Now that’s what you call choice. No matter who you are, Expedia puts the world within your reach. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Annapolis holiday?
Make sure your next holiday in Annapolis is one to remember by visiting its well-known attractions. U.S. Naval Academy, Maryland State House, William Paca House and Chesapeake Bay Bridge are just a few of the things we recommend seeing while you’re in the area.
What are the best neighbourhoods to stay in when on holiday in Annapolis?
There are many places to book a hotel in Annapolis, but one of the most in-demand is Historic District. There’s plenty here to keep you on the go, including Maryland State House. Alternatively, make Naval Academy your base. U.S. Naval Academy is among this neighbourhood’s famous attractions.
Do I need a visa for my Annapolis holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and reason for visiting, whether it be for work or holidays, will determine if you need a visa for Annapolis. Also ensure your passport is up to date and has a minimum of six months validity remaining after your return date. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Annapolis holiday?
Do some research into the types of things people in Annapolis wear, and maybe even check out fashion pages on social media for inspiration. You’ll want to create a versatile travel wardrobe full of pieces that work for your destination and showcase your unique style. Pack with confidence by monitoring the forecast in Annapolis. July brings the warmest temperatures, with daytime averages of 25ºC, while January days average 1ºC, making it the coolest time of year.
What does an Expedia Annapolis holiday include?
Select from a combination of hire cars, flights and hotels. Once you’ve made your booking, add some tours and experiences. Want to pick your airfare class? That’s easy to do too. The choice is all yours when it comes to crafting your dream Annapolis trip. Expedia features different types of properties, with the most sought after in Annapolis including private holiday homes and apartments. With Expedia, you’ll always enjoy the flexibility and freedom to tailor-make your holiday however you like.
Does Expedia offer Book Now, Pay Later Annapolis holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that work for all budget sizes, so you can lock in that well-deserved holiday sooner.
  • No-deposit holidays: When you see an awesome deal but don’t have the full amount yet, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with an Annapolis Expedia holiday?
Yes — and it’s simple too. Expedia has access to more than 400 partner airlines worldwide. Our holiday packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.

Discover the most popular places to visit in Annapolis

Image for U.S. Naval Academy

U.S. Naval Academy

4.5/5(5 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
Image for Chesapeake Bay Bridge

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Image for Sandy Point State Park

Sandy Point State Park

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

Unmissable things to do in Annapolis

Image for Phantoms of Annapolis Ghost Tour By US Ghost Adventures

Phantoms of Annapolis Ghost Tour By US Ghost Adventures

£24
Per adult
Phantoms of Annapolis Ghost Tour By US Ghost Adventures
Image for Phantoms of Annapolis Ghost Walking Tour

Phantoms of Annapolis Ghost Walking Tour

£20
Per adult
Phantoms of Annapolis Ghost Walking Tour
Image for Walking Ghost Tour of Historic Annapolis by Annapolis Ghost Tours

Walking Ghost Tour of Historic Annapolis by Annapolis Ghost Tours

£21
Per adult
Walking Ghost Tour of Historic Annapolis by Annapolis Ghost Tours
See all activities in Annapolis

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.