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Chesapeake Bay Vacation Packages

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $653, price is now $544 per person
$544
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly aparthotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Price was $884, price is now $765 per person
$765
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Short Pump Town Center and Short Pump Village are located nearby.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
Price was $1,136, price is now $629 per person
$629
per person
Dec 10 - Dec 15
found 4 hours 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 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.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,174, price is now $863 per person
$863
per person
Nov 24 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Book a stay at this boutique hotel in Williamsburg. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Historic Jamestowne are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $732, price is now $583 per person
$583
per person
Dec 10 - Dec 15
found 4 hours 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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Price was $780, price is now $628 per person
$628
per person
Dec 10 - Dec 15
found 4 hours 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.
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $967, price is now $793 per person
$793
per person
Dec 10 - Dec 15
found 4 hours 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.
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was $829, price is now $698 per person
$698
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Price was $969, price is now $821 per person
$821
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was $880, price is now $752 per person
$752
per person
Dec 10 - Dec 15
found 4 hours 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.
Embassy Suites Williamsburg

Embassy Suites Williamsburg

3.5 out of 5
Price was $819, price is now $702 per person
$702
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Rochambeau Roadside Inn

Rochambeau Roadside Inn

3 out of 5
Price was $918, price is now $792 per person
$792
per person
Dec 10 - Dec 15
found 4 hours 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.

3-4 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Richmond North Glen Allen by IHG

Candlewood Suites Richmond North Glen Allen by IHG

2.5 out of 5
Price was $696, price is now $556 per person
$556
per person
Nov 15 - Nov 18
just found
Roundtrip flight included
New York (LGA) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $906, price is now $800 per person
$800
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $638, price is now $569 per person
$569
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Richmond (RIC)
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was $740, price is now $687 per person
$687
per person
Nov 21 - Nov 24
found 1 day ago
Roundtrip flight included
Houston (IAH) to Richmond (RIC)

5-7 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $732, price is now $583 per person
$583
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $1,136, price is now $629 per person
$629
per person
Dec 10 - Dec 15
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $1,394, price is now $916 per person
$916
per person
Nov 24 - Nov 30
found 16 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,174, price is now $863 per person
$863
per person
Nov 24 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)

Chesapeake Bay Last Minute Hotel Deals

Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore

2.5 out of 5
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. ...
Hampton Inn & Suites Exmore - Eastern Shore
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
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 ...
Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
Shore Stay Suites

Shore Stay Suites

2 out of 5
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 ...
Shore Stay Suites
Quality Inn & Suites

Quality Inn & Suites

2 out of 5
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. ...
Quality Inn & Suites
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Stay at this hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton Inn Gloucester
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
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 ...
King’s Creek Resort by Spinnaker
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
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 ...
Comfort Suites Airport
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Book a stay at this business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Inn & Suites Hampton near Coliseum
See all 6,852 properties in Chesapeake Bay
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.