Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

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

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,264, price is now CA $1,084 per person
CA $1,084
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) 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 Water Country USA are located nearby.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was CA $1,313, price is now CA $1,107 per person
CA $1,107
per person
Jul 9 - Jul 12
found 21 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, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Kings Creek Plantation by TripForth

Kings Creek Plantation by TripForth

3.5 out of 5
Price was CA $1,993, price is now CA $1,687 per person
CA $1,687
per person
Jun 30 - Jul 5
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
Stay at this vacation home in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was CA $1,638, price is now CA $1,400 per person
CA $1,400
per person
Jul 9 - Jul 12
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Short Pump
Price was CA $1,340, price is now CA $1,147 per person
CA $1,147
per person
Jul 9 - Jul 12
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this spa hotel in Richmond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Short Pump Town Center and Elk's Lodge are located nearby.
Quirk Hotel Richmond

Quirk Hotel Richmond

4 out of 5
Downtown Richmond
Price was CA $1,347, price is now CA $1,167 per person
CA $1,167
per person
Jul 9 - Jul 12
found 21 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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway 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 $1,084. 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

Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
The price is CA $217 per night
CA $217
CA $610 total
May 17 - May 18
includes taxes & fees
Stay at this cottage in Eastville. Enjoy laundry facilities and air conditioning. Popular attractions Cape Charles Beach and Wilkins Beach are located nearby.
Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
4129 Lankford Hwy Exmore VA
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $149 total
May 24 - May 25
includes taxes & fees
Stay at this hotel in Exmore. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Northampton Shopping Center and Exmore Town Park are located nearby.
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $151 total
May 17 - May 18
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Pet-friendly
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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.