Holidays to Chesapeake Bay

Choose two or more items and save on your trip:
Choose two or more items and save on your trip:

Hotels, flights, car hire & activities - all in one place! Bundle everything you need for your holiday to Chesapeake Bay and save

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

    4.5/5Wonderful!(156 area reviews)

    Art galleries, museums and theaters as well as vibrant entertainment, nightlife and shopping districts await in this city center neighborhood.

    Find hotels in Downtown Washington D.C.
  • Baltimore showing interior views and art

    Inner Harbor

    1 out of top 10 points of interest in this area

    The captivating waterfront views and popular shops are just a few highlights of Inner Harbor. Make a stop by Baltimore Inner Harbor Marina or National Aquarium in Baltimore while you're exploring the area.

    Find hotels in Inner Harbor
  • Georgetown which includes street scenes, heritage architecture and a house

    Georgetown

    4.5/5Wonderful!(14 area reviews)

    Discover some of Washington’s oldest buildings, upscale shops and vibrant nightlife in this elegant riverside suburb.

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  • Capitol Hill, Washington, District of Columbia, United States of America

    Capitol Hill

    4/5Very Good!(41 area reviews)

    Home to the emblematic U.S. Capitol Building, this central neighborhood is famous for its historic landmarks, markets, museums and nightlife.

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  • Downtown Baltimore, Baltimore, Maryland, United States of America

    Downtown Baltimore

    4/5Very Good!(24 area reviews)

    Business and financial trading blend with historical architecture, baseball, live music, museums and theaters in the energetic city center of Baltimore.

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Chesapeake Bay Hotel Deals

Washington Plaza
Washington Plaza
4 out of 5
10 Thomas Circle NW, Washington, DC, 20005
The price is £113 per night from 5 Sep to 6 Sep
Stay at this 4-star business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool and breakfast. Our guests praise the breakfast and the bar in their ...
4.3/5 Excellent! (2,086 reviews)
Friendly, convenient and had a nice pool.
"I was working nearby so it was very convenient. The staff was extremely friendly and helpful. I also enjoyed going to the pool when I was done work. The restaurant and bar in sight made it easy to grab a bite with little hassle. Overall it was a great stay."

Reviewed on 5 Aug 2022

Washington Plaza
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
3 out of 5
550 C St SW, Washington, DC, 20024
The price is £137 per night from 5 Sep to 6 Sep
Stay at this 3-star business-friendly aparthotel in Washington. Enjoy free WiFi, an outdoor pool and 2 restaurants. Our guests praise the helpful staff and the ...
4.1/5 Very Good! (2,368 reviews)
"Nice place to stay, was near a lot of things."

Reviewed on 8 Aug 2022

Holiday Inn Washington Capitol - Natl Mall, an IHG Hotel
The Madison Hotel
The Madison Hotel
4.5 out of 5
1177 15th Street NW, Washington, DC, 20005
The price is £156 per night from 20 Aug to 21 Aug
Stay at this 4.5-star luxury aparthotel in Washington. Enjoy free WiFi, breakfast and a 24-hour fitness centre. Our guests praise the helpful staff and the comfy ...
4.3/5 Excellent! (1,082 reviews)
"We had an excellent stay at the Madison hotel. The staff are extremely friendly, the rooms are clean and the beds are very comfortable. It is centrally located near with all the main attractions at walking distance."

Reviewed on 6 Aug 2022

The Madison Hotel
See all 8605 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 vacation package cost?
From as low as , you can build your own Chesapeake Bay vacation package. Simply combine flights, hotels and car rentals and we’ll reward you with discounts.
If I'm not able to travel, can I cancel my Chesapeake Bay vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For further information, check out our Customer Service Portal. But generally speaking, if you’ve made your booking in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
How do I get a cheap travel package to Chesapeake Bay?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we’ve got them all. Pick and choose the combination that suits you and save as much as . And of course, we do get that a travel package is never a one-size-fits-all. That’s why we offer more than 400 airlines and 1,000,000 properties around the globe, so you can build your very own custom-built Chesapeake Bay getaway.
When is the best time of year to visit Chesapeake Bay?
If saving money is your priority, is the best time to take a break in Chesapeake Bay. is usually the most expensive month, so you’ll need a bigger travel budget if you visit then. are the high season months and when this destination is often at its most exciting. Clear space in your calendar for if you’d prefer a quieter escape.
How far in advance should I book my Chesapeake Bay vacation?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to a year in advance. This is often the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Chesapeake Bay are still known to appear in the weeks leading up to departure.
What does an Expedia Chesapeake Bay travel package include?
You can choose from a combination of flights, hotels and rental cars. Once you’ve made your booking, you can add the fun stuff like tours and activities. Want to pick your fare class? That’s possible too. The choice is yours when it comes to arranging your dream Chesapeake Bay escape.
What should I know before booking a Chesapeake Bay travel package?
Booking all the parts of your getaway together is an excellent way to save. Combine your car rentals, airfares and hotels into a tidy little package. But it’s not just hotels. Expedia offers all kinds of properties, including vacation rentals like oceanfront condos and spacious residences. The list goes on!
Does Expedia offer Book Now, Pay Later Chesapeake Bay vacation packages?
If you’re itching to explore but aren’t able to cough up the dough, Expedia can lend a hand with a custom payment option. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your dream getaway today.
Can I choose my airline with a Chesapeake Bay Expedia vacation package?
Expedia offers access to more than 400 airline partners globally, so you certainly can. Simply select your preferred carrier and create the perfect Chesapeake Bay escape.
Can I travel to Chesapeake Bay right now?
Find information about Chesapeake Bay quarantine policies, travel restrictions and more by going to our Covid-19 Travel Advisor.

Popular places to visit in Chesapeake Bay

Image for Confederate Memorial Park

Confederate Memorial Park

Explore the great outdoors at Confederate Memorial Park, a lovely green space in Scotland. Wander the beautiful beaches in this relaxing area.

Confederate Memorial Park
Image for Slack Winery

Slack Winery

You can enjoy a tasting or tour at Slack Winery during your travels to Ridge. Wander the beautiful beaches in this relaxing area.

Slack Winery
Image for Elms Beach Park

Elms Beach Park

If a restful holiday is part of your travel plans, Elms Beach Park might be the perfect place to visit during your trip to Lexington Park. Visit the shops in this family-friendly area or simply enjoy its restaurants.

Elms Beach Park

Things to do

Image for Mount Vernon and Old Town Alexandria Day Trip from Washington DC

Mount Vernon and Old Town Alexandria Day Trip from Washington DC

£67
Per adult
88% of travellers recommend
Mount Vernon and Old Town Alexandria Day Trip from Washington DC
Image for DC at Dusk Night Tour

DC at Dusk Night Tour

£48
Per adult
94% of travellers recommend
DC at Dusk Night Tour
Image for Grand Tour of Washington DC with Arlington Cemetery Entry & Trolley Pass

Grand Tour of Washington DC with Arlington Cemetery Entry & Trolley Pass

£81
Per adult
Grand Tour of Washington DC with Arlington Cemetery Entry & Trolley Pass
See all activities in Chesapeake Bay