Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Save 100% on your flight
Price was $530, price is now $353 per person
$353
per person
Jan 5 - Jan 12
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $707, price is now $426 per person
$426
per person
Jan 5 - Jan 12
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.
The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $572, price is now $367 per person
$367
per person
Jan 22 - Jan 26
found 21 hours ago
Roundtrip flight included
Boston (BOS) 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.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Save 100% on your flight
Price was $686, price is now $453 per person
$453
per person
Jan 5 - Jan 12
found 22 hours ago
Roundtrip 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.
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Save 100% on your flight
Price was $626, price is now $414 per person
$414
per person
Jan 5 - Jan 12
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features an indoor pool and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $694, price is now $462 per person
$462
per person
Jan 22 - Jan 26
found 21 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.

Frequently asked questions

How much are vacation packages to Chesapeake Bay?
Travelocity offers flight and hotel vacation packages starting at an incredible $353. 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

Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
$368 nightly
The price is $410 total per night
$410 total
Nov 30 - Dec 1
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
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $95 total per night
$95 total
Dec 7 - Dec 8
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Crown Inn Motel

Crown Inn Motel

2 out of 5
7833 George Washington Memorial Highway Yorktown VA
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $68 total per night
$68 total
Nov 30 - Dec 1
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, dry cleaning, and laundry facilities are also on offer.
Parking included
Free WiFi
Don't see what you're looking for?
See all available properties in Chesapeake Bay
View all properties
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.