Chesapeake Bay Vacations 2025 from CA $699

Chesapeake Bay flight + hotel packages

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

Westgate Historic Williamsburg Resort

per person

Feb. 20 - Feb. 26

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3.5-star family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, 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.

Fort Magruder Historic Williamsburg, Trademark by Wyndham

per person

Jan. 30 - Feb. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3.5-star business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.

Bluegreen Vacations Patrick Henry Square, Ascend Resort

per person

Jan. 30 - Feb. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.

Kingsmill Resort

Kingsmill

per person

Jan. 30 - Feb. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Kingsmill Plantation Golf Course are located nearby.

Camp Cardinal Gloucester Point

per person

Jan. 30 - Feb. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this family-friendly cabin in Hayes. Enjoy free parking, an outdoor pool, and cable TV channels. Popular attractions Severn Yachting Center and Gloucester County Public Library 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 $156

CA $181 total

includes taxes & fees

1 Jan - 2 Jan 2025

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 Smithsonian Institution are located nearby.

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $171

CA $242 total

includes taxes & fees

1 Jan - 2 Jan 2025

Book a stay at this 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 Smithsonian Institution are located nearby.

Hotel Washington

515 15th Street, NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $274

CA $376 total

includes taxes & fees

1 Jan - 2 Jan 2025

Stay at this 4.5-star luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and National Mall are located nearby.

Hilton Garden Inn Reagan National Airport

2020 Richmond Highway, Arlington, VA

Free cancellation

Reserve now, pay when you stay

CA $134

CA $153 total

includes taxes & fees

2 Jan - 3 Jan 2025

Stay at this 3.5-star business-friendly hotel in Arlington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the bar and the helpful staff in our reviews. Popular attractions National Mall and Smithsonian Institution are located nearby.

Sheraton Pentagon City Hotel

900 S Orme St, Arlington, VA

Free cancellation

Reserve now, pay when you stay

CA $122

CA $139 total

includes taxes & fees

2 Jan - 3 Jan 2025

Stay at this 3.5-star business-friendly hotel in Arlington. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions White House and National Mall are located nearby.

citizenM Washington DC Capitol

550 School St SW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $156

CA $181 total

includes taxes & fees

1 Jan - 2 Jan 2025

Stay at this 4-star business-friendly hotel in Washington. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the bar in our reviews. Popular attractions National Mall and Smithsonian Institution 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

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 entertainment choices and great live music.

National Mall

4.5/5(198 reviews)

Explore the great outdoors with a trip to National Mall, a popular green space in Washington. Experience the area's fascinating museums and acclaimed theater scene.

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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible CA $699. 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.