Chesapeake Bay Vacation Packages 2025/2026 from $241

Chesapeake Bay flight + hotel vacation packages

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

Vacation Village At Williamsburg

Save 100% on your flight

$241

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) 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.

Club Wyndham Kingsgate

Save 100% on your flight

$263

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Richmond (RIC)

This Colonial resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the mini golf, children's pool, and arcade/game room. Enjoy the indoor pool and perks like free self parking and free WiFi.

Holiday Inn Club Vacations Williamsburg Resort by IHG

Save 100% on your flight

$446

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Richmond (RIC)

This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. There's fun for all ages with a free kid's club and a bowling alley, and families will appreciate the convenience store. Business travelers can take advantage of the business center.

The Colonies at Williamsburg

Save 100% on your flight

$300

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) 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.

Wingate by Wyndham Richmond Short Pump

Short Pump

Save 100% on your flight

$309

per person

Nov 6 - Nov 10

found 14 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Richmond (RIC)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$126 total

per night

Oct 5 - Oct 6

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

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$188 total

per night

Oct 31 - Nov 1

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

citizenM Washington DC Capitol

550 School St SW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$150 total

per night

Oct 31 - Nov 1

This hotel features 2 restaurants and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A communal living room, express check-in, and express check-out are also on offer.

Free WiFi

Restaurant

Renaissance Baltimore Harborplace Hotel

202 E Pratt St, Baltimore, MD

$189 total

per night

Oct 19 - Oct 20

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and laundry facilities and concierge services are also offered.

Pool

Pet friendly

State Plaza Hotel

2116 E Street NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$167 total

per night

Nov 1 - Nov 2

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a garden are also offered.

Free WiFi

Restaurant

YOTEL Washington DC

415 New Jersey Ave Nw, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$188 total

per night

Oct 19 - Oct 20

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Pool

Pet friendly

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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

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.

National Mall

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

White House

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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible $241. 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.