Chesapeake Bay Vacations 2025/2026 from CA $685

Chesapeake Bay flight + hotel packages

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

Vacation Village At Williamsburg

CA $685

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3-star spa hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Jamestown Settlement are located nearby.

Linden Row Inn

Downtown Richmond

CA $1,087

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip 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.

Graduate by Hilton Richmond

Downtown Richmond

CA $1,115

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4-star business-friendly hotel in Richmond. Enjoy free WiFi, 2 restaurants, and a rooftop terrace. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Club Wyndham Kingsgate

CA $808

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3-star family-friendly resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.

Wingate by Wyndham Richmond Short Pump

Short Pump

CA $826

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip 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.

Top Chesapeake Bay hotels deals

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $172

CA $242 total

Sep 4 - Sep 5

includes taxes & fees

Stay at this 4-star business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $150

CA $174 total

Sep 7 - Sep 8

includes taxes & fees

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.

Hyatt Regency Baltimore Inner Harbor

300 Light Street, Baltimore, MD

Free cancellation

Reserve now, pay when you stay

CA $219

CA $258 total

Sep 4 - Sep 5

includes taxes & fees

Stay at this 4-star eco-certified hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions National Aquarium in Baltimore and Baltimore Inner Harbor Marina are located nearby.

Hotel Arboretum

1917 Bladensburg Rd, NE, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $113

CA $131 total

Sep 4 - Sep 5

includes taxes & fees

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 Capital One Arena and Smithsonian Institution are located nearby.

AC Hotel by Marriott Arlington National Landing

1999 Richmond Highway, Arlington, VA

Free cancellation

Reserve now, pay when you stay

CA $164

CA $187 total

Sep 19 - Sep 20

includes taxes & fees

Stay at this 4-star business-friendly hotel in Arlington. Enjoy breakfast (surcharge), 24-hour room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Arlington National Cemetery and National Mall are located nearby.

State Plaza Hotel

2116 E Street NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $150

CA $174 total

Sep 4 - Sep 5

includes taxes & fees

Stay at this 3.5-star business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and National Mall are located nearby.

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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.

National Mall

4.5/5(198 reviews)

National Mall is just one of the places to see in Washington, so why not enjoy the other things to explore during your travels? Experience the area's acclaimed art scene and fascinating museums.

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 theater scene and great live music.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible CA $685. 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.