Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was CA $1,007, price is now CA $945 per person
CA $945
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
Book a stay at this family-friendly B&B in Richmond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Richmond Raceway and Maymont Park 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 $1,467, price is now CA $1,152 per person
CA $1,152
per person
Oct 23 - Oct 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Merchants Square are located nearby.
Rochambeau Roadside Inn

Rochambeau Roadside Inn

2 out of 5
Price was CA $2,147, price is now CA $1,852 per person
CA $1,852
per person
Oct 23 - Oct 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Water Country USA are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,388, price is now CA $1,222 per person
CA $1,222
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 Richmond Raceway are located nearby.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was CA $1,612, price is now CA $1,462 per person
CA $1,462
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 Maymont Park 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 $1,389, price is now CA $1,280 per person
CA $1,280
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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 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 $945. 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 $244 per night
CA $244
CA $648 total
Sep 7 - Sep 8
includes taxes & fees
Stay at this cottage in Eastville. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Cape Charles Beach and Wilkins Beach are located nearby.
Hot tub
Kitchen
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 $153 per night
CA $153
CA $170 total
Aug 13 - Aug 14
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
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 $147 per night
CA $147
CA $164 total
Sep 6 - Sep 7
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.
Pool
Breakfast included
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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.