Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $521, price is now $368 per person
$368
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the express check-out, laundry service, and conference space. You'll also find 6 outdoor tennis courts and an indoor pool.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $919, price is now $453 per person
$453
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was $825, price is now $599 per person
$599
per person
Sep 24 - Sep 27
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Save 100% on your flight
Price was $632, price is now $465 per person
$465
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
2 outdoor pools, 3 hot tubs, and an indoor pool are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the picnic area. Enjoy the gym and perks like free self parking and free WiFi.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $737, price is now $544 per person
$544
per person
Sep 24 - Sep 27
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Save 100% on your flight
Price was $655, price is now $488 per person
$488
per person
Oct 6 - Oct 11
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible $368. 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
$431 nightly
The price is $500 total per night
$500 total
Aug 9 - Aug 10
Total with taxes and fees
This cottage features a gym and a hot tub. Laundry facilities are provided for your convenience.
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
$98 nightly
The price is $110 total per night
$110 total
Aug 10 - Aug 11
Total with taxes and fees
This hotel features an outdoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, dry cleaning, and laundry facilities are also on offer.
Pool
Breakfast included
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
$106 nightly
The price is $118 total per night
$118 total
Jul 20 - Jul 21
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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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.