Chesapeake Bay Vacation Packages 2025 from $496

Chesapeake Bay flight + hotel vacation packages

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

Wingate by Wyndham Richmond Short Pump

Short Pump

per person

Jun 2 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Barsala At Sphere Apartments

Save 100% on your flight

per person

Jun 2 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Richmond (RIC)

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

Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

per person

Jun 2 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Richmond (RIC)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.

The Commonwealth

Downtown Richmond

per person

Jun 2 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Richmond (RIC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.

The Berkeley Hotel

Downtown Richmond

per person

Jun 2 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Richmond (RIC)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station 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

$126

includes taxes & fees

$109 per night

Apr 20 - Apr 21

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

Hilton Garden Inn Reagan National Airport

2020 Richmond Highway, Arlington, VA

Free Cancellation

Reserve now, pay when you stay

$144

includes taxes & fees

$126 per night

Apr 26 - Apr 27

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

Free airport shuttle

Pet friendly

Omni Shoreham Hotel

2500 Calvert St Nw, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$193

includes taxes & fees

$166 per night

Apr 20 - Apr 21

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

State Plaza Hotel

2116 E Street NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$173

includes taxes & fees

$149 per night

Apr 20 - Apr 21

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

Generator Hotel Washington DC

1900 Connecticut Ave NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$170

includes taxes & fees

$146 per night

May 4 - May 5

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a coffee shop, and a terrace are also offered.

Pool

Pet friendly

Hotel Nell - Union Market

411 New York Ave NE, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$147

includes taxes & fees

$127 per night

Apr 27 - Apr 28

This smoke-free hotel features 2 restaurants and 2 bars/lounges. Enjoy the a rooftop terrace and perks like free WiFi. Self parking, a coffee shop, and dry cleaning are also offered.

Pet friendly

Free WiFi

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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.

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.

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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible $496. 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.