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 $383, price is now $309 per person
$309
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game room and barbecue grills. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $2,113, price is now $1,592 per person
$1,592
per person
Mar 14 - Mar 20
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
A full-service spa, 2 restaurants, and 6 outdoor tennis courts are all featured at this luxury hotel. You'll appreciate the indoor pool, bar/lounge, and concierge services.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $1,081, price is now $815 per person
$815
per person
Mar 14 - Mar 20
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the express check-out and WiFi in public areas. You'll also find 6 outdoor tennis courts and an indoor pool.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,266, price is now $968 per person
$968
per person
Mar 14 - Mar 20
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
This boutique hotel features an attached winery, a full-service spa, and a restaurant. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.
The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was $512, price is now $399 per person
$399
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station are also on offer.
Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was $1,037, price is now $834 per person
$834
per person
Mar 14 - Mar 20
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. Bring the family and enjoy the free kid's club, bowling alley, and kid-friendly dining. Business travelers can take advantage of the business center.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible $309. 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
This condo features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
$294 nightly
The price is $328 total per night
$328 total
Jan 13 - Jan 14
Total with taxes and fees
This inn features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.
Breakfast included
Parking included
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway

Cape Charles VA
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
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.