Chesapeake Bay Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 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

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 street scenes, night scenes and a city

Downtown Washington D.C.

1 out of top 10 points of interest in this area
4.5/5(156 area reviews)

Known for its fascinating museums and important monuments, there's plenty to explore in Downtown Washington D.C.. Check out top attractions like Franklin Square and National Museum of Women in the Arts, and jump on the metro at McPherson Sq. Station or Center Station to see more of the city.

Find hotels in Downtown Washington D.C.

Top hotels in Chesapeake Bay

Washington Plaza Hotel
Washington Plaza Hotel
4 out of 5
10 Thomas Circle NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is S$173 per night from 9 Jan to 10 Jan
S$173
includes taxes & fees
9 Jan - 10 Jan
8.6/10 Excellent! (3,977 reviews)
"Good location but expensive breakfast."

Reviewed on 2 Jan,2025

Washington Plaza Hotel
Hamilton Hotel Washington DC
Hamilton Hotel Washington DC
4 out of 5
1001 14th St NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 10 Jan to 11 Jan
S$247
includes taxes & fees
10 Jan - 11 Jan
8.6/10 Excellent! (2,063 reviews)
"The property is very beautiful and pleasant, clean and safe is also conveniently located. The only thing that did not convince me was the attention of the receptionists, even before arriving I called to ask about the parking lot and they answered me; I don't know I don't have a vehicle, a non-professional ..."

Reviewed on 2 Jan,2025

Hamilton Hotel Washington DC
Hotel Washington
Hotel Washington
5 out of 5
515 15th Street, NW, Washington, DC
Fully refundableReserve now, pay when you stay
The price is S$372 per night from 10 Jan to 11 Jan
S$372
includes taxes & fees
10 Jan - 11 Jan
8.8/10 Excellent! (2,203 reviews)
"At 1 am the lady on the front desk was absent for 30 minutes, she didn’t leave any note or sign, when she came back she was unprofessional and with bad manners."

Reviewed on 3 Jan,2025

Hotel Washington
See all 13,845 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.

Frequently asked questions

How much does a Chesapeake Bay holiday package cost?
Tailor make your Chesapeake Bay package from an affordable . Choose from any combination of hotels, flights and rental cars to build the trip of your dreams. Don’t forget to add on some tours and experiences!
How do I get a cheap travel package to Chesapeake Bay?
Crafting your own Chesapeake Bay holiday package with Expedia is a smart way to save. We have access to more than 550 airlines and 1,000,000 properties around the world. With such an awesome range to pick from, you’ll have no hassles putting together your dream escape.
Where should I stay in Chesapeake Bay?
To explore well-known attractions such as White House and Washington Monument, Washington is the place to be. Lots of travellers also adore Baltimore, home to National Aquarium in Baltimore and Oriole Park at Camden Yards. If time is on your side, why not visit both cities?
What are the top hotels in Chesapeake Bay?
For hotels in Ocean City with comfy beds and friendly service, you can’t go past Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel. If you’re visiting Washington as well, you’ll get a solid night’s sleep at Luxor Hotel and Casino or Circus Circus Hotel, Casino & Theme Park.
How far in advance should I book my Chesapeake Bay holiday?
Smart travellers often book early. You can normally start comparing international fares on Expedia up to 12 months before your intended flight. If you’re purchasing tickets last minute, there’s no need to worry. Budget prices occasionally appear just weeks prior to departure.
What does an Expedia Chesapeake Bay travel package include?
Rental cars, flights and hotels, or any combination of the three — it’s totally up to you. Whether you’re headed to Chesapeake Bay with the family or adventuring solo, there’s a bundle to suit every style and budget. Once you’ve made your booking, why not add on some tours as well?
What should I know before booking a Chesapeake Bay travel package?
You can save big by bundling your hotels, flights and rental cars. Once you’ve made your booking, you can add on things like activities or tours. Your next unforgettable adventure is only a few clicks away.
If I'm not able to travel, can I cancel my Chesapeake Bay holiday package?
You can. We get that even the best-laid plans can go awry, so we’re happy to help if you need to make changes to your Chesapeake Bay holiday package. It may be possible to change or cancel your itinerary at no cost if you’ve booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Popular places to visit

White House

White House

4/5(142 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
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
United States Capitol

United States Capitol

4.5/5(144 reviews)

Sitting on top of Capitol Hill is a Washington landmark that’s been the home of American democracy for more than 200 years.

United States Capitol

What to do in Chesapeake Bay

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

S$48
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

S$109
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Annapolis Ghost Tour: Phantoms of Annapolis

S$34
per adult
Annapolis Ghost Tour: Phantoms of Annapolis
See all activities in Chesapeake Bay

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.