Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was CA $1,091, price is now CA $947 per person
CA $947
per person
Jan 23 - Jan 29
found 22 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 an outdoor pool. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $2,356, price is now CA $1,529 per person
CA $1,529
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this luxury 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 Altria Theater are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was CA $1,943, price is now CA $1,496 per person
CA $1,496
per person
Dec 26 - Jan 2
found 17 hours 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 Merchants Square are located nearby.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,569, price is now CA $1,291 per person
CA $1,291
per person
Dec 26 - Dec 31
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this 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 Merchants Square are located nearby.
Rochambeau Williamsburg

Rochambeau Williamsburg

3 out of 5
Price was CA $1,852, price is now CA $1,567 per person
CA $1,567
per person
Dec 26 - Jan 2
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 free bicycles on site. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was CA $1,704, price is now CA $1,448 per person
CA $1,448
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Altria Theater 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 $947. 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

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

2.5 out of 5
3446 Lankford Hwy Exmore VA
Free cancellation
The price is CA $144 per night
CA $144
CA $161 total
Dec 4 - Dec 5
includes taxes & fees
Book a stay at this business-friendly hotel in Exmore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Northampton Shopping Center and Exmore Town Park are located nearby.
Pool
Breakfast included
Waterfront Oasis with Crabs, Oysters and Mother Nature

Waterfront Oasis with Crabs, Oysters and Mother Nature

Hacksneck VA
Book a stay at this beach vacation home in Hacksneck. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Eastern Shore Yacht and Country Club Golf Course and The Blue Crow Antique Mall are located nearby.
Kitchen
Washer
Beachfront Estate, Multi-Level Decks, Bay Creek

Beachfront Estate, Multi-Level Decks, Bay Creek

Cape Charles VA
Book a stay at this beach vacation home in Cape Charles. Enjoy a beach locale, a water park, and a fitness center. Popular attractions Bay Creek Golf Club and Cape Charles Harbor are located nearby.
Pool
Kitchen
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.