Search Deals onChesapeake Bay Vacation Packages
Chesapeake Bay Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort
Save 100% on your flight
Price was $1,030, price is now $498 per person
$498
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Griffin Hotel, an official Colonial Williamsburg Hotel
Price was $1,203, price is now $984 per person
$984
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy 3 outdoor pools, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Wedmore Place
Price was $967, price is now $733 per person
$733
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Historic Jamestowne are located nearby.
Club Wyndham Governor’s Green
Price was $977, price is now $767 per person
$767
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, 2 outdoor pools, and 3 hot tubs. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
The Colonies at Williamsburg
Price was $674, price is now $531 per person
$531
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, and free water park access. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Bowlero Williamsburg are located nearby.
Holiday Inn Club Vacations Williamsburg Resort by IHG
Price was $799, price is now $649 per person
$649
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly resort in Williamsburg. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Popular attractions Williamsburg Premium Outlets and MagiQuest are located nearby.
The Commonwealth
Price was $1,216, price is now $1,003 per person
$1,003
per person
Oct 14 - Oct 19
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury hotel in Richmond. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Richmond Raceway and Richmond Old City Hall are located nearby.
Rochambeau Roadside Inn
Price was $833, price is now $689 per person
$689
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Williamsburg. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Vacation Village At Williamsburg
Price was $619, price is now $516 per person
$516
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa aparthotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Jamestown Settlement are located nearby.
Omni Richmond Hotel
Price was $1,040, price is now $869 per person
$869
per person
Oct 14 - Oct 19
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Richmond Raceway and Canal Walk are located nearby.
Stay-Over Suites
Price was $662, price is now $566 per person
$566
per person
Oct 14 - Oct 19
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this golf hotel in Hopewell. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions U.S. Army Women's Museum and U.S. Army Quartermaster Museum are located nearby.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Price was $662, price is now $567 per person
$567
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
3-4 Night Vacations in Chesapeake Bay
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Chesapeake Bay
Price found within the past 48 hours. Click for updated prices.
Chesapeake Bay Last Minute Hotel Deals
Hampton Inn & Suites Exmore - Eastern Shore
4129 Lankford Hwy Exmore VA
Stay at this hotel in Exmore. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
3446 Lankford Hwy Exmore VA
Book a stay at this business-friendly hotel in Exmore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Tides Inn
480 King Carter Dr Irvington VA
Book a stay at this beach hotel in Irvington. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Steamboat Era Museum and Historic ...
Shore Stay Suites
26406 Lankford Hwy Cape Charles VA
Stay at this hotel in Cape Charles. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. ...
Quality Inn & Suites
25297 Lankford Hwy Onley VA
Stay at this hotel in Onley. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
King’s Creek Resort by Spinnaker
191 Cottage Cove Lane Williamsburg VA
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and ...
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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