Chesapeake Bay Vacation Packages 2025/2026 from $420

Chesapeake Bay flight + hotel vacation packages

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

Tourist Homes of Richmond Church Hill North

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

Barsala At Sphere Apartments

Save 100% on your flight

per person

Aug 27 - Sep 1

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A virtual front desk are provided for your convenience.

The Commonwealth

Downtown Richmond

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Hilton Richmond Downtown

Downtown Richmond

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) 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.

Linden Row Inn

Downtown Richmond

per person

Sep 26 - Sep 29

found 1 day ago

Roundtrip non-stop flight included

Houston (IAH) to Richmond (RIC)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage 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

$109 nightly

$126 total

Aug 3 - Aug 4

Total includes taxes and fees

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

Reserve now, pay when you stay

$152 nightly

$176 total

Aug 17 - Aug 18

Total includes taxes and fees

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

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$157 total

Aug 4 - Aug 5

Total includes taxes and fees

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

Sheraton Pentagon City Hotel

900 S Orme St, Arlington, VA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$106 total

Jul 26 - Jul 27

Total includes taxes and fees

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

Crowne Plaza College Park - Washington DC by IHG

6400 Ivy Lane, Greenbelt, MD

Free Cancellation

$83 nightly

$94 total

Aug 10 - Aug 11

Total includes taxes and fees

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

Hotel Arboretum

1917 Bladensburg Rd, NE, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$117 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.

Breakfast included

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

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 $420. 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.