Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was CA $1,207, price is now CA $994 per person
CA $994
per person
Jan 14 - Jan 20
found 8 hours 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 Water Country USA are located nearby.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,347, price is now CA $1,066 per person
CA $1,066
per person
Dec 30 - Jan 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was CA $1,414, price is now CA $1,144 per person
CA $1,144
per person
Feb 6 - Feb 12
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Jamestown Settlement are located nearby.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was CA $1,223, price is now CA $1,015 per person
CA $1,015
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this 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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was CA $1,429, price is now CA $1,197 per person
CA $1,197
per person
Dec 30 - Jan 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this 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.
Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was CA $1,295, price is now CA $1,094 per person
CA $1,094
per person
Dec 30 - Jan 4
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this family-friendly resort in Williamsburg. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Popular attractions Williamsburg Premium Outlets and MagiQuest are located nearby.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible CA $994. 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.

Top Chesapeake Bay hotel deals

Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
The price is CA $514 per night
CA $514
CA $573 total
Dec 1 - Dec 2
includes taxes & fees
Stay at this inn in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodville Park and White Marsh Shopping Center are located nearby.
Breakfast included
Parking included
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $133 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hampton Coliseum and Peninsula Town Center are located nearby.
Pool
Breakfast included
Crown Inn Motel

Crown Inn Motel

2 out of 5
7833 George Washington Memorial Highway Yorktown VA
Free cancellation
Reserve now, pay when you stay
The price is CA $81 per night
CA $81
CA $95 total
Dec 1 - Dec 2
includes taxes & fees
Stay at this motel in Yorktown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions York Village and Hampton Roads Harley-Davidson are located nearby.
Parking 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.

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