Chesapeake Bay Vacations 2025 from CA $720

Chesapeake Bay flight + hotel packages

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

A house full of steel balls and games

Dumbarton

per person

May 27 - Jun. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this family-friendly B&B in Richmond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Carytown and Richmond Raceway are located nearby.

Linden Row Inn

Downtown Richmond

Save 100% on your flight

per person

May 27 - Jun. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3-star historic hotel in Richmond. Enjoy free WiFi, a 24-hour front desk, and 2 meeting rooms. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

The Commonwealth

Downtown Richmond

Save 100% on your flight

per person

May 27 - Jun. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Wingate by Wyndham Richmond Short Pump

Short Pump

per person

May 27 - Jun. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Short Pump Town Center and Elk's Lodge are located nearby.

Virginia Crossings Hotel, Tapestry Collection by Hilton

per person

May 27 - Jun. 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3.5-star golf hotel in Glen Allen. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Richmond Raceway and The Crossings Golf Club are located nearby.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $168

CA $195 total

includes taxes & fees

16 Mar - 17 Mar

Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Holiday Inn Washington Capitol - Natl Mall by IHG

550 C St SW, Washington, DC

Free cancellation

CA $261

CA $303 total

includes taxes & fees

23 Mar - 24 Mar

Stay at this 3-star business-friendly hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Smithsonian Institution and Capital One Arena are located nearby.

Pool

Pet-friendly

Arlo Washington DC

333 G St NW, Washington, DC

Free cancellation

CA $240

CA $337 total

includes taxes & fees

16 Mar - 17 Mar

Stay at this 4-star hotel in Washington. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Popular attractions Capital One Arena and Union Station Shopping Center are located nearby.

Pool

Pet-friendly

Crowne Plaza College Park - Washington DC by IHG

6400 Ivy Lane, Greenbelt, MD

Free cancellation

CA $126

CA $143 total

includes taxes & fees

21 Mar - 22 Mar

Stay at this 3.5-star business-friendly hotel in Greenbelt. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbelt Park and NASA Visitor Center are located nearby.

Pet-friendly

Parking included

Hotel Arboretum

1917 Bladensburg Rd, NE, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $292

CA $338 total

includes taxes & fees

17 Mar - 18 Mar

Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Breakfast included

Free WiFi

Generator Hotel Washington DC

1900 Connecticut Ave NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $176

CA $246 total

includes taxes & fees

13 Apr - 14 Apr

Stay at this hotel in Washington. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

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

5/5(3 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.

White House

4/5(388 reviews)

Find out about the history of White House, one of the top monuments in Washington. Experience the area's acclaimed art scene and great live music.

Virginia Beach Boardwalk

5/5(49 reviews)

Virginia Beach Boardwalk is just one of the places to see in Virginia Beach, so why not enjoy the other things to explore during your travels? Wander the beautiful beaches and seaside in this family-friendly area.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible CA $720. 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.