Exclusive Chesapeake Bay Vacation Deals

Chesapeake Bay vacation package deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Richmond I-64 Short Pump Area by IHG

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

2.5 out of 5
Price was $475, price is now $352 per person
$352
per person
Feb 13 - Feb 16
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $540, price is now $370 per person
$370
per person
Feb 7 - Feb 10
found 10 hours ago
Roundtrip flight included
Boston (BOS) 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.
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $569, price is now $424 per person
$424
per person
Feb 13 - Feb 16
found 2 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.
Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
Price was $485, price is now $364 per person
$364
per person
Feb 13 - Feb 16
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was $501, price is now $377 per person
$377
per person
Feb 13 - Feb 16
found 2 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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $723, price is now $544 per person
$544
per person
Feb 13 - Feb 16
found 2 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 $352. 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 8 - Jan 9
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
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.