Chesapeake Bay Vacations 2025 from CA $1,100

Chesapeake Bay flight + hotel packages

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

Quirk Hotel Richmond

Downtown Richmond

per person

Jun. 1 - Jun. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4-star business-friendly hotel in Richmond. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Barsala At Sphere Apartments

Save 100% on your flight

per person

Jun. 1 - Jun. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 3.5-star aparthotel in Richmond. Enjoy free WiFi, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Broad Street and Richmond Raceway are located nearby.

Graduate by Hilton Richmond

Downtown Richmond

per person

Jun. 1 - Jun. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4-star business-friendly hotel in Richmond. Enjoy free WiFi, an outdoor pool, 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.

Hilton Richmond Downtown

Downtown Richmond

per person

Jun. 1 - Jun. 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4-star business-friendly hotel in Richmond. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Vacation Village At Williamsburg

per person

May 29 - Jun. 5

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.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $159

CA $185 total

includes taxes & fees

Apr 20 - Apr 21

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

Apr 17 - Apr 18

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 White House and Capital One Arena are located nearby.

Pool

Hot tub

Hilton Garden Inn Reagan National Airport

2020 Richmond Highway, Arlington, VA

Free cancellation

Reserve now, pay when you stay

CA $154

CA $176 total

includes taxes & fees

Apr 18 - Apr 19

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 Arlington National Cemetery and National Mall are located nearby.

Free airport shuttle

Pet-friendly

State Plaza Hotel

2116 E Street NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $184

CA $213 total

includes taxes & fees

Apr 13 - Apr 14

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.

Free WiFi

Restaurant

Generator Hotel Washington DC

1900 Connecticut Ave NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $165

CA $232 total

includes taxes & fees

Apr 18 - Apr 19

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

Hotel Nell - Union Market

411 New York Ave NE, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $191

CA $221 total

includes taxes & fees

Apr 18 - Apr 19

Stay at this 3-star hotel in Washington. Enjoy 2 restaurants, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Union Station Shopping Center and Capital One Arena are located nearby.

Pet-friendly

Free WiFi

Don't see what you're looking for?

See all available properties in Chesapeake Bay

View all properties

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 entertainment choices.

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 great live music and acclaimed art scene.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?

Travelocity offers flight and hotel vacation packages starting at an incredible CA $1,100. 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.