Chesapeake Bay Vacations 2025 from CA $1,163

Chesapeake Bay flight + hotel packages

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

Westgate Historic Williamsburg Resort

per person

Jul 6 - Jul 12

found 1 day 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.

Warner Hall

per person

Jul 6 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3-star inn in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodville Park and White Marsh Shopping Center are located nearby.

Patriots Inn

per person

Jul 6 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Book a stay at this business-friendly motel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.

Vacation Village At Williamsburg

per person

Jul 6 - Jul 12

found 1 day ago

Roundtrip non-stop 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.

The Colonies at Williamsburg

per person

Jul 6 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3-star family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, and free water park access. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Bowlero Williamsburg 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 $178

CA $207 total

includes taxes & fees

May 30 - May 31

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.

Pool

Free WiFi

Omni Shoreham Hotel

2500 Calvert St Nw, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $185

CA $255 total

includes taxes & fees

Jun 13 - Jun 14

Stay at this 4-star family-friendly hotel in Washington. Enjoy an outdoor pool, 2 bars/lounges, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Smithsonian's National Zoo and White House are located nearby.

Pool

Hot tub

Hamilton Hotel Washington DC

1001 14th St NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $177

CA $248 total

includes taxes & fees

Jun 29 - Jun 30

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 Capital One Arena are located nearby.

Free WiFi

Restaurant

citizenM Washington DC NoMa

1222 1ST STREET NE, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $199

CA $231 total

includes taxes & fees

Jun 29 - Jun 30

Stay at this 4-star business-friendly hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Free WiFi

Restaurant

Generator Hotel Washington DC

1900 Connecticut Ave NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $154

CA $219 total

includes taxes & fees

Jun 28 - Jun 29

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 Smithsonian's National Zoo and White House are located nearby.

Pool

Pet-friendly

Vacation Village At Williamsburg

4870 Longhill Road, Williamsburg, VA

Free cancellation

Reserve now, pay when you stay

CA $131

CA $165 total

includes taxes & fees

Jun 11 - Jun 12

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.

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

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 theater scene and fascinating museums.

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 theater scene and entertainment choices.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible CA $1,163. 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.