A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

Annapolis Holidays from £793

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Top Annapolis flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 24 Sept - 29 Sept

    Hotel Indigo Old Town Alexandria by IHG + Flight

    Old Town Alexandria
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,006 reviews)
    "Awesome!"
    Reviewed August 3, 2026
    Return London (LON) - Baltimore (BWI)
    LHR - IADDirect IAD - LHRDirect
    £1,115
    £793
    per traveller
    found 1 day ago
    Hotel Indigo Old Town Alexandria by IHG
  • 24 Sept - 29 Sept

    Willard InterContinental Washington by IHG + Flight

    Downtown Washington D.C.
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,002 reviews)
    Return London (LON) - Baltimore (BWI)
    LHR - IADDirect IAD - LHRDirect
    Save 100% on your flight
    £3,244
    £2,424
    per traveller
    found 1 day ago
    Willard InterContinental Washington by IHG
  • 24 Sept - 29 Sept

    The Hay-Adams + Flight

    Downtown Washington D.C.
    5 nights
    5.0 star property
    9.6/10 - Exceptional (906 reviews)
    Return London (LON) - Baltimore (BWI)
    LHR - IADDirect IAD - LHRDirect
    £2,055
    £1,604
    per traveller
    found 1 day ago
    The Hay-Adams
  • 9 Sept - 14 Sept

    Sofitel Washington DC Lafayette Square + Flight

    Downtown Washington D.C.
    5 nights
    5.0 star property
    9.0/10 - Wonderful (1,235 reviews)
    Return Birmingham (BHX) - Baltimore (BWI)
    BHX - IAD1 stop IAD - BHX1 stop
    £1,369
    £1,073
    per traveller
    found 1 day ago
    Sofitel Washington DC Lafayette Square
  • 9 Sept - 14 Sept

    Hotel Washington + Flight

    Downtown Washington D.C.
    5 nights
    5.0 star property
    9.0/10 - Wonderful (2,453 reviews)
    Return Birmingham (BHX) - Baltimore (BWI)
    BHX - IAD1 stop IAD - BHX1 stop
    £1,352
    £1,062
    per traveller
    found 1 day ago
    Hotel Washington

Where to stay in Annapolis

Find the best Annapolis areas for the activities you enjoy most.

Historic District

Step back in time as you wander through Annapolis's Historic District. Cobblestone streets wind past America's oldest working state capitol and brick townhouses dating to the 1700s. The majestic US Naval Academy grounds offer a glimpse into military tradition. City Dock buzzes with maritime activity where tall ships dock against a colonial backdrop. Explore waterfront restaurants serving fresh Chesapeake seafood and boutique shops housed in centuries-old buildings. History buffs will appreciate the William Paca House and Thurgood Marshall Memorial.

Eastport

Across the bridge from city centre Annapolis lies maritime Eastport, a charming peninsula defined by its waterfront character. Historic homes and converted maritime buildings line quiet streets that lead to scenic walks along the Severn River and Back Creek. The Annapolis Maritime Museum showcases the area's nautical heritage and working waterfront past. "Restaurant Row" on Severn Avenue buzzes with waterfront dining where fresh Chesapeake Bay seafood takes centre stage. Local marinas display classic workboats alongside modern yachts. The neighborhood's walkable streets and waterfront promenades offer peaceful spaces to enjoy salt air and harbour views.

West Annapolis

West Annapolis offers a peaceful slice of Maryland living with tree-lined streets and well-maintained homes. This charming residential area sits near the Severn River and College Creek, providing scenic water views. Visitors can enjoy uncrowded pavements perfect for contemplative morning strolls among mature trees. The area serves as a quiet gateway to nearby attractions. Navy-Marine Corps Memorial Stadium and Thurgood Marshall Memorial are just outside its boundaries. City centre Annapolis with its historic sites is a short drive away. Morning bird songs and fresh Chesapeake Bay breezes create a refreshing retreat from busier tourist areas.

Murray Hill

Murray Hill offers a charming retreat just steps from Annapolis's historic centre. Colonial-era homes line quiet streets where mature oaks create peaceful canopies. The area balances residential calm with easy access to maritime attractions along the Chesapeake Bay. Visitors can stroll to city centre shops and restaurants in minutes. Ballet Theatre of Maryland and Spa Creek provide cultural and natural highlights. History lovers will appreciate the authentic architecture while enjoying a genuine local experience away from tourist crowds.

Hillsmere

Hillsmere offers a peaceful retreat on Annapolis's outskirts where tree-lined streets lead to community waterfront access. This family-friendly area balances suburban comfort with natural beauty along the South River and Chesapeake Bay. Maryland Quiet Waters Park provides scenic trails for outdoor enthusiasts. Visitors can explore the local Great Frogs Winery or take a quick 15-minute drive to city centre Annapolis attractions. The neighborhood's small marina welcomes kayakers and boaters seeking authentic waterfront living without tourist crowds.

Discover the most popular places to visit in Annapolis

What to do in Annapolis

Annapolis Hotel Deals

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.

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.