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
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3.5-star 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.
Delta Hotels by Marriott Richmond Downtown
per person
May 29 - Jun 2
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3.5-star business-friendly hotel in Richmond. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Vacation Village At Williamsburg
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star spa hotel 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.
Holiday Inn Club Vacations Williamsburg Resort by IHG
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3.5-star 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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star 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.
Club Wyndham Governor’s Green
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star 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
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star 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.
Club Wyndham Kingsgate
per person
Jun 19 - Jun 22
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star family-friendly resort in Williamsburg. Enjoy free WiFi, free parking, 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.
Chesapeake Bay Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chesapeake Bay Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, May 7 - Sat, May 10
MCO
Orlando Intl.
RIC
Richmond Intl.
$73 Roundtrip, found 2 days ago
$73
Roundtrip
found 2 days ago
Thu, May 1 - Wed, May 7
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$78 Roundtrip, found 13 hours ago
$78
Roundtrip
found 13 hours ago
Wed, Jul 30 - Sat, Aug 2
MCO
Orlando Intl.
ORF
Norfolk Intl.
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Fri, May 16 - Mon, May 19
MIA
Miami Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 6 hours ago
$88
Roundtrip
found 6 hours ago
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