Chesapeake Bay Vacation Packages 2025/2026 from $323

Chesapeake Bay flight + hotel vacation packages

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

Super 8 by Wyndham Williamsburg/Historic Area

per person

Aug 26 - Aug 31

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. WiFi in public areas is free. The front desk is staffed around-the-clock and barbecue grills are on offer.

Kingsmill Resort

Kingsmill

Save 100% on your flight

per person

Aug 26 - Aug 31

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.

Warner Hall

Save 100% on your flight

per person

Aug 26 - Aug 31

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

This inn features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.

Wyndham Garden Williamsburg Busch Gardens Area

per person

Aug 26 - Aug 31

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

This hotel features a 24-hour gym and a seasonal outdoor pool. 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.

Days Inn & Suites by Wyndham Williamsburg Colonial

per person

Aug 26 - Aug 31

found 22 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and onsite conference space. A computer station, laundry facilities, and free newspapers are also on offer.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Get rates

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

Omni Shoreham Hotel

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

900 S Orme St, Arlington, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

2019 Pennsylvania Ave Nw, Washington, DC

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, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.

Free WiFi

Restaurant

Crowne Plaza College Park - Washington DC by IHG

6400 Ivy Lane, Greenbelt, MD

Free Cancellation

Get rates

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-in are also offered.

Pet friendly

Parking included

Don't see what you're looking for?

See all available properties in Chesapeake Bay

View all properties

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

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.

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.

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 $323. 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.