Chesapeake Bay Vacation Packages 2025/2026 from $265

Chesapeake Bay flight + hotel vacation packages

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

Club Wyndham Kingsgate

$265

per person

Nov 3 - Nov 6

found 8 hours ago

Roundtrip flight included

Boston (BOS) 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

Save 100% on your flight

$290

per person

Nov 3 - Nov 6

found 8 hours 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.

The Colonies at Williamsburg

Save 100% on your flight

$323

per person

Nov 3 - Nov 6

found 8 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.

The Commonwealth

Downtown Richmond

Save 100% on your flight

$355

per person

Nov 3 - Nov 6

found 8 hours ago

Roundtrip flight included

Boston (BOS) 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.

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$268

per person

Nov 3 - Nov 6

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

Free water park access and an outdoor pool are featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like continental 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

$99 nightly

$115 total

Aug 22 - Aug 23

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

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$147 total

Aug 31 - Sep 1

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

The Henley Park Hotel

926 Massachusetts Ave NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$110 total

Aug 28 - Aug 29

Total includes taxes and fees

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. A lobby fireplace, express check-out, and luggage storage are also on offer.

Free WiFi

Restaurant

State Plaza Hotel

2116 E Street NW, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$115 total

Aug 24 - Aug 25

Total includes taxes and fees

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

Hotel Arboretum

1917 Bladensburg Rd, NE, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Sep 1 - Sep 2

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

Omni Shoreham Hotel

2500 Calvert St Nw, Washington, DC

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$149 total

Sep 3 - Sep 4

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

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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 $265. 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.