Chesapeake Bay Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chesapeake Bay Holiday

Set off on a thrilling adventure with a holiday package to Chesapeake Bay. This destination's history are just one of the things that make this place a visitor favourite. Kick off your trip to Chesapeake Bay with a couple of days in Washington visiting popular attractions like National Mall and White House. Baltimore is another top city that draws crowds from near and far. National Aquarium in Baltimore and Oriole Park at Camden Yards are two of the top places to see in this destination. When it's time to stop dreaming and start discovering, Expedia will help turn your Chesapeake Bay holiday into a reality.

Our guide on where to stay in Chesapeake Bay

Find the best Chesapeake Bay areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake Bay
Downtown Washington D.C. showing a city, night scenes and street scenes

Downtown Washington D.C.

1 out of top 10 points of interest in this area
4.5/5(95 area reviews)

Shopping, fine dining and museums aplenty: Downtown really is where the business happens.

Find hotels in Downtown Washington D.C.

Chesapeake Bay Holiday

Chesapeake Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Ronald Reagan Washington National Airport (DCA)
Top Sights
National Mall, Deep Creek Lake and National Aquarium in Baltimore

Our pick of the best Chesapeake Bay Hotel Deals

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW, Washington, DC
The price is AU$191 per night from 5 Oct to 6 Oct
AU$191
5 Oct - 6 Oct
includes taxes & fees
8.6/10 Excellent! (4,718 reviews)
A Great Find
"Really appreciated the extra touches offered by the hotel. The staff was friendly and helpful, offering assistance at every turn. We are an older couple who had never used Uber. They instructed us on how to use the App and gave us confidence that it was safe and reliable. The hotel itself was attractive, ..."

Reviewed on 30 Sept 2025

Washington Plaza Hotel
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
1001 14th St NW, Washington, DC
The price is AU$261 per night from 31 Oct to 1 Nov
AU$261
31 Oct - 1 Nov
includes taxes & fees
8.6/10 Excellent! (2,824 reviews)
"Front desk persons very friendly, helpful, welcoming and professional! They will make us come back! Room was very clean and pressure of the water in the shower was great! Balcony view was great specially in the morning we saw Dolphins…beautiful! So far our best experience in Panama City Beach!"

Reviewed on 30 Sept 2025

Hamilton Hotel Washington DC
citizenM Washington DC Capitol

citizenM Washington DC Capitol

4 out of 5
550 School St SW, Washington, DC
The price is AU$226 per night from 31 Oct to 1 Nov
AU$226
31 Oct - 1 Nov
includes taxes & fees
8.8/10 Excellent! (2,841 reviews)
"Cabin was very small but also exactly as described and pictured, failed to realize the room was 'cabin-size". Only a tiny bit larger than a cruise ship cabin. Would have been great for just me but was getting cramped after 2 days with my wife. Lime scooters all around nearby and St. Dominic's cathedral/church ..."

Reviewed on 1 Oct 2025

citizenM Washington DC Capitol
See all 15,234 properties in Chesapeake Bay
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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Chesapeake Bay

Busch Gardens Williamsburg

Busch Gardens Williamsburg

Have a fun-filled day at Busch Gardens Williamsburg and find out why this is a popular theme park in Williamsburg. Experience the entertainment choices or attend a sporting event in this family-friendly area.

Busch Gardens Williamsburg
National Mall showing an administrative building, heritage architecture and a city

National Mall

4.5/5(22 reviews)

Washington’s famous strip is teeming with American history in each and every monument and museum that you’ll see.

National Mall
White House

White House

4/5(84 reviews)

Explore the home and workplace of the president of the United States. See entertainment areas and state rooms and learn about the history of this famous building.

White House

What to do in Chesapeake Bay

Washington DC National Monuments by Moonlight Trolley Tour

Washington DC Monuments by Moonlight Night Trolley Tour

AU$72
per adult
92% of travellers recommend
Washington DC Monuments by Moonlight Night Trolley Tour
Capitol Building in Washington DC

One day tour Washington & Philadelphia from New York

AU$143
per adult
88% of travellers recommend
One day tour Washington & Philadelphia from New York
Cruise boat with Capitol Building in the background in Washington DC

Spirit of Washington D.C. Signature Lunch Cruise

AU$112
per adult
78% of travellers recommend
Spirit of Washington D.C. Signature Lunch Cruise
See all activities in Chesapeake Bay

Frequently asked questions

Can I cancel my flight booking to Chesapeake Bay due to COVID-19?
Many airlines now offer more flexibility due to COVID-19. Our convenient Customer Service Portal will help answer most questions about changes to your flight. It's also worth checking the terms and conditions of your chosen carrier — preferably before booking!
What's the best way to find cheap flights to Chesapeake Bay that have flexible change policies?
At Expedia, we've been channeling our inner yogi to bring you the most flexible airfares around. Simply check the "No change fee" box directly underneath the filter subheading "Flexible change policies" to find your perfect flight to Chesapeake Bay.
What are some of the general tips for travellers to Chesapeake Bay during the COVID-19 outbreak?
COVID-19 may have changed how we travel, but it hasn't stifled our passion for exploring. Here are some tips on how to cope with travel's new challenges:
  • Before locking in your flight, find out if any travel bans or restrictions apply — in both your origin and destination. Get up-to-date information by checking government and travel websites.
  • Requirements state you must wear a face mask throughout your travel experience, even at screening checkpoints. You should be prepared to lower your mask to verify your identity when asked by a TSA employee.
  • Rather than handing a TSA officer your boarding pass, place it straight on the reader yourself. After that, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be removed for screening.
  • Remove personal items from your pocket, such as your wallet, coins and keys, and put them in your carry-on rather than the bins. This will reduce handling during screening.
  • Transport your food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on means it's less likely a TSA officer will need to open and touch your bag for inspection.

Which airlines fly to Chesapeake Bay?
American Airlines is a leading airline servicing Chesapeake Bay. Search for airfares to Salisbury - Ocean City Wicomico Regional Airport (SBY) and you'll have 178 American Airlines flights every month to choose from.
How can I find cheap tickets to Chesapeake Bay?
A useful strategy for finding cheap tickets is to be flexible with your travel dates. Start by searching for your flight to Chesapeake Bay, then click on the "flexible dates" box to compare prices for nearby days. Want another good tip? Book well ahead of time. To give you an idea of fares, was the lowest price for a flight to Chesapeake Bay in the last seven days.
How much is a flight to Chesapeake Bay?
One-way trips departing from () sold for as little as in the last seven days. During this period, the cost of a return airfare to Chesapeake Bay varied between and . If you find a fantastic deal, grab it quickly — these fares don't hang around for long.
What are the most popular airports to fly into in Chesapeake Bay?
Zip up your suitcase and fly into Salisbury - Ocean City Wicomico Regional Airport (SBY), Chesapeake Bay's leading flight hub. Book a seat on one of the 178 flights that touch down at this awesome destination each month.
When is the cheapest time to fly to Chesapeake Bay?
Fly out on a Tuesday to improve your chances of picking up the cheapest deal to Chesapeake Bay. Mondays are usually the next most affordable day to take off. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Chesapeake Bay?
In the last seven days, tickets to Chesapeake Bay ranged between and . Prices rise as your travel date nears, so snap up a top deal today.
Which airlines with flights to Chesapeake Bay employ COVID-19 cleanliness policies?
While travelling during an ongoing pandemic can be challenging, airlines have worked around the clock to protect the well-being of passengers and crew. These are a few carriers that have introduced changes:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

Explore a world of travel with Expedia

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