Deals on vacations and trips to Chesapeake Bay

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Chesapeake Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Tourist Homes of Richmond Church Hill North

Tourist Homes of Richmond Church Hill North

4 out of 5
per person
Aug 29 - Aug 31
found 23 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Richmond (RIC)
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
per person
Aug 29 - Aug 31
found 22 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Richmond (RIC)
2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.
Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (MDW) to Richmond (RIC)
This aparthotel includes free WiFi in public areas and a virtual front desk.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
per person
Aug 29 - Aug 31
found 22 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Richmond (RIC)
A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Richmond (RIC)
This traditional hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
10 Thomas Circle NW, Washington, DC
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the 24-hour gym, poolside bar, and concierge services.
Pool
Free WiFi
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
2500 Calvert St Nw, Washington, DC
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Families will appreciate the children's pool and picnic area. Enjoy the outdoor pool and perks like free WiFi.
Pool
Hot Tub
Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
900 S Orme St, Arlington, VA
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, express check-in, and free airport shuttle. A free shopping center shuttle is offered as well.
Free airport shuttle
Pet friendly
Hotel Lombardy

Hotel Lombardy

4 out of 5
2019 Pennsylvania Ave Nw, Washington, DC
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
Free WiFi
Restaurant
Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

4 out of 5
202 E Pratt St, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and limo/town car service are also offered.
Pet friendly
Free WiFi
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
1001 14th St NW, Washington, DC
Free Cancellation
Reserve now, pay when you stay
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This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a terrace and multilingual staff can provide around-the-clock assistance.
Free WiFi
Restaurant
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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.

Popular places to visit

Christmastown at Busch Gardens, Williamsburg

Busch Gardens Williamsburg

4.5/5(1,024 reviews)

Enjoy the excitement at Busch Gardens Williamsburg and see why people love this amusement park in Williamsburg. Experience the entertainment choices or attend a sporting event in this family-friendly area.

Busch Gardens Williamsburg
White House which includes a city, an administrative buidling and heritage architecture

White House

4/5(5,961 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
National Mall which includes heritage architecture, an administrative buidling and a city

National Mall

4.5/5(4,017 reviews)

Inspiring architecture, magnificent museums and the icons of American history await on Washington’s famous two-mile (three-kilometer) strip.

National Mall

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible $395. With such huge savings, you’ll be saying hello to Chesapeake Bay before you know it.
Where can I get the best vacation package deals for Chesapeake Bay?
Travelocity has all you need to score an amazing Chesapeake Bay package deal. Select from as many as 400 air carriers and 1,000,000 hotels worldwide and craft a travel itinerary that’s suited to you. With this amount of choice, it’s time to start planning your next big adventure.
Why should I purchase my Chesapeake Bay vacation package with Travelocity?
Because we believe in crafting one-of-a-kind vacation experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our customer support team is available 24/7 to ensure you’ll never roam alone. We also have a Price Match Guarantee, so you can secure your trip knowing you’ve landed the best deal around. If you find a lower price, we’ll match it!
Will I save money on my Chesapeake Bay car rental if I book it with my hotel or flight?
You certainly can with our Chesapeake Bay vacation packages. With one of these, there are lots of ways to stretch your vacation budget further. Bundle any two or more car, flight, hotel and tour bookings and watch your savings start to pile up. With your own ride, all the popular attractions in and around Chesapeake Bay are an unforgettable road trip away.
Which airport is best for Chesapeake Bay?
The most popular airports for Chesapeake Bay are Norfolk Intl. Airport (ORF) and Newport News - Williamsburg Intl. Airport (PHF).
What is there to do in Chesapeake Bay?
Chesapeake Bay has hidden gems at every turn, but be sure you visit White House and United States Capitol while you’re in town. These attractions can’t be missed.

Photos of local treasures

Browse Chesapeake Bay vacation photos for more inspiration

USS Wisconsin BB-64 featuring a marina
Virginia featuring a garden, modern architecture and a city
Peabody Institute of the John Hopkins University
Norfolk Botanical Garden which includes a garden, landscape views and a pond
USS Wisconsin BB-64 which includes a bay or harbor and military items