Chesapeake Bay Vacations 2025/2026 from CA $1,136

Chesapeake Bay flight + hotel packages

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

Club Wyndham Patriots’ Place

CA $1,136

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this hotel in Williamsburg. Enjoy free WiFi, free parking, and a 24-hour fitness center. 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.

Warner Hall

CA $1,964

per person

Nov 4 - Nov 11

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.

King’s Creek Resort by Spinnaker

CA $1,175

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4.5-star luxury condo in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

Club Wyndham Kingsgate

CA $1,212

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop 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.

Kingsmill Resort

Kingsmill

CA $1,546

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

Stay at this 4-star 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 Water Country USA 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 $211

CA $287 total

Sep 21 - Sep 22

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.

Free WiFi

Restaurant

Washington Plaza Hotel

10 Thomas Circle NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $151

CA $175 total

Sep 21 - Sep 22

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.

Pool

Free WiFi

Hyatt Regency Baltimore Inner Harbor

300 Light Street, Baltimore, MD

Free cancellation

Reserve now, pay when you stay

CA $234

CA $275 total

Sep 28 - Sep 29

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.

Pool

Pet-friendly

Holiday Inn Express Washington DC Downtown by IHG

317 K St NW, Washington, DC

Free cancellation

CA $156

CA $181 total

Sep 21 - Sep 22

includes taxes & fees

Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Capital One Arena and Smithsonian Institution are located nearby.

Breakfast included

Pet-friendly

Hotel Arboretum

1917 Bladensburg Rd, NE, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $144

CA $167 total

Sep 21 - Sep 22

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.

Breakfast included

Free WiFi

State Plaza Hotel

2116 E Street NW, Washington, DC

Free cancellation

Reserve now, pay when you stay

CA $151

CA $175 total

Sep 21 - Sep 22

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.

Free WiFi

Restaurant

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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 fascinating museums 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 $1,136. 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.