Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Price was $646, price is now $462 per person
$462
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $1,501, price is now $963 per person
$963
per person
Nov 24 - Nov 30
found 5 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.
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was $1,134, price is now $934 per person
$934
per person
Nov 24 - Nov 30
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features free WiFi in public areas, concierge services, and valet parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. A terrace, a computer station, and luggage storage are also on offer.
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $1,123, price is now $953 per person
$953
per person
Nov 24 - Nov 30
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Free WiFi in public areas, a terrace, and a garden are available at this hotel. A picnic area, express check-out, and luggage storage are also on offer.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $649, price is now $554 per person
$554
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $811, price is now $695 per person
$695
per person
Nov 24 - Nov 30
found 5 hours ago
Roundtrip flight included
Boston (BOS) 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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible $462. 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

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
$80 nightly
The price is $89 total per night
$89 total
Oct 16 - Oct 17
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
$95 nightly
The price is $106 total per night
$106 total
Oct 19 - Oct 20
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.
Pool
Breakfast included
Beachfront Estate, Multi-Level Decks, Bay Creek

Beachfront Estate, Multi-Level Decks, Bay Creek

Cape Charles VA
A water park and a gym are featured at this smoke-free vacation home. A garden, laundry facilities, and barbecue grills are also on offer.
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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.

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