Annapolis Holidays from £713
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Your Annapolis Holiday
Book a custom holiday package to Annapolis and get ready to experience this fascinating city how you like. Consider spending time in the neighbourhood of Historic District, which is good for history and tons more. If a sightseeing tour is part of the programme during your trip to Annapolis, stop by leading attractions like U.S. Naval Academy, Maryland State House and William Paca House. Check out Expedia's wide range of travel options and book your ideal holiday to Annapolis now.
Top Annapolis Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Fairmont Washington, D.C., Georgetown
Northwest
£1,004
per person
25 Nov - 2 Dec
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.6/10 Exceptional! (1,003 reviews)
One of the best customer service hotels I’ve stayed in a very long time, highly recommend. Fantastic property.
Reviewed on 18 Sept 2026
Where to stay in Annapolis
Find the best Annapolis areas and neighborhoods for the activities you enjoy most. Learn more about Annapolis
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.
Eastport
While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.
Murray Hill
If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.
Hillsmere
While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.
Admiral Heights
If you're looking for some top things to see and do in Admiral Heights and surrounding area, you can visit Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts.
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 |
Top hotels in Annapolis
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
£71
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,187 reviews)
"Housekeeping did not change the bedding is was dried blood in the bed"
Reviewed on 18 Sept 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
£110
12 Oct - 13 Oct
includes taxes & fees
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
£94
27 Sept - 28 Sept
includes taxes & fees
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
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.
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.
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.
Navy-Marine Corps Memorial Stadium
9.2/10 (287 reviews)
Home to the Navy Midshipmen teams, this stadium honours 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.
Westfield Annapolis Mall
8.8/10 (394 reviews)
Westfield Annapolis offers over 200 stores, from luxury boutiques to popular department stores. Explore high-end fashion, dine at diverse restaurants, or catch a film at the state-of-the-art theatre.
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.
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 theatre.
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.
What to do in Annapolis
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
£7
per traveller
80% of travellers recommend
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
£22
per adult
Tipsy History Tour: 300+ Years of Annapolis Drinking History
£29
per adult
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.
Explore a world of travel with Expedia
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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. Flight-inclusive packages are ATOL protected.
