Chesapeake Bay Vacations 2025/2026 from CA $1,343

Chesapeake Bay flight + hotel packages

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

Barsala At Sphere Apartments

per person

Sep 16 - Sep 21

found 14 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

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

Warner Hall

per person

Oct 2 - Oct 9

found 4 hours 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.

The Commonwealth

Downtown Richmond

per person

Sep 16 - Sep 21

found 14 hours 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.

Graduate by Hilton Richmond

Downtown Richmond

per person

Sep 16 - Sep 21

found 14 hours 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 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.

Linden Row Inn

Downtown Richmond

per person

Sep 16 - Sep 21

found 14 hours 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.

Top Chesapeake Bay hotels deals

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $136

CA $158 total

Aug 4 - Aug 5

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 National Museum of African American History and Culture are located nearby.

Pool

Free WiFi

Omni Shoreham Hotel

2500 Calvert St Nw, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $169

CA $236 total

Aug 1 - Aug 2

includes taxes & fees

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 National Museum of African American History and Culture 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 $127

CA $189 total

Aug 4 - Aug 5

includes taxes & fees

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 National Museum of African American History and Culture are located nearby.

Free WiFi

Restaurant

Sheraton Pentagon City Hotel

900 S Orme St, Arlington, VA

Free cancellation

Reserve now, pay when you stay

CA $128

CA $146 total

Aug 22 - Aug 23

includes taxes & fees

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 Arlington National Cemetery and National Museum of African American History and Culture are located nearby.

Free airport shuttle

Pet-friendly

Crowne Plaza College Park - Washington DC by IHG

6400 Ivy Lane, Greenbelt, MD

Free cancellation

CA $114

CA $129 total

Aug 24 - Aug 25

includes taxes & fees

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

Get rates

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

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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

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

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 entertainment choices and acclaimed theater scene.

White House

Find out about the history of White House, one of the top monuments in Washington. Experience the area's fascinating museums 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 $1,343. 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.