Chesapeake Bay Vacation Packages 2025 from $308

Chesapeake Bay flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Historic Williamsburg Resort

Save 100% on your flight

per person

Sep 6 - Sep 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.

The Colonies at Williamsburg

Save 100% on your flight

per person

Sep 6 - Sep 10

found 13 hours ago

Roundtrip flight included

Boston (BOS) 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.

Vacation Village At Williamsburg

Save 100% on your flight

per person

Sep 6 - Sep 10

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

Save 100% on your flight

per person

Sep 6 - Sep 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the express check-out and WiFi in public areas. You'll also find 6 outdoor tennis courts and an indoor pool.

Barsala At Sphere Apartments

Save 100% on your flight

per person

Sep 6 - Sep 10

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This aparthotel includes free WiFi in public areas and a virtual front desk.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free Cancellation

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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

2500 Calvert St Nw, Washington, DC

Free Cancellation

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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

Hotel Lombardy

2019 Pennsylvania Ave Nw, Washington, DC

Free Cancellation

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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

202 E Pratt St, Baltimore, MD

Free Cancellation

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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.

Sheraton Pentagon City Hotel

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

Hamilton Hotel Washington DC

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible $308. 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.