Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Williamsburg

Wingate by Wyndham Williamsburg

2.5 out of 5
Price was CA $1,308, price is now CA $966 per person
CA $966
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Water Country USA are located nearby.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Price was CA $3,070, price is now CA $2,364 per person
CA $2,364
per person
Feb 28 - Mar 7
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this luxury hotel in Williamsburg. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was CA $1,920, price is now CA $1,495 per person
CA $1,495
per person
Feb 24 - Mar 3
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 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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was CA $1,964, price is now CA $1,540 per person
CA $1,540
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this 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.
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,433, price is now CA $1,158 per person
CA $1,158
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this 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.
Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club Greensprings Williamsburg

3 out of 5
Price was CA $1,303, price is now CA $1,054 per person
CA $1,054
per person
Apr 9 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jamestown Settlement and Williamsburg Premium Outlets 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 $966. 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

Perfect Cozy Vacation Rental on the Eastern Shore

Perfect Cozy Vacation Rental on the Eastern Shore

Cape Charles VA
Stay at this condo in Cape Charles. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cape Charles Museum & Welcome Center and Oyster Farm Marina are located nearby.
Kitchen
Washer
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
The price is CA $417 per night
CA $417
CA $465 total
Jan 19 - Jan 20
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
Coastal Bliss: Beach Front. Hot Tub. Firepit. Kayaks. 3500SQFT.

Coastal Bliss: Beach Front. Hot Tub. Firepit. Kayaks. 3500SQFT.

Cape Charles VA
Book a stay at this family-friendly vacation home in Cape Charles. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Kiptopeke State Park and Eastern Shore of Virginia National Wildlife Refuge are located nearby.
Hot tub
Kitchen
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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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