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Chesapeake Bay Vacation Packages

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Ashland Studio Inn By OYO Richmond North near Kings Dominion

Ashland Studio Inn By OYO Richmond North near Kings Dominion

2.5 out of 5
Price was $499, price is now $448 per person
$448
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
Stay at this motel in Ashland. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Kings Dominion and Banks Tennis Center are located nearby.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $1,185, price is now $958 per person
$958
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $734, price is now $629 per person
$629
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Price was $1,002, price is now $884 per person
$884
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Broad Street and 1708 Gallery are located nearby.
Turnpike Motel Richmond VA by Hotel O US 60

Turnpike Motel Richmond VA by Hotel O US 60

2.5 out of 5
Price was $559, price is now $494 per person
$494
per person
Apr 25 - May 1
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Broad Street and Maymont Park are located nearby.
Eagle Inn by Hotel O Richmond Midlothian Turnpike

Eagle Inn by Hotel O Richmond Midlothian Turnpike

2.5 out of 5
Price was $572, price is now $507 per person
$507
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free WiFi, free parking, and room service. Popular attractions Broad Street and Maymont Park are located nearby.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Price was $830, price is now $742 per person
$742
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and The National are located nearby.
The Virginia Cliffe Inn

The Virginia Cliffe Inn

2.5 out of 5
Price was $1,179, price is now $1,054 per person
$1,054
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Stay at this B&B in Glen Allen. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Cultural Arts Center Glen Allen and Lavender Fields Herb Farm are located nearby.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Price was $1,249, price is now $1,137 per person
$1,137
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Embassy Suites by Hilton Richmond

Embassy Suites by Hilton Richmond

3.5 out of 5
Price was $907, price is now $827 per person
$827
per person
Apr 25 - May 1
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bowlero West End and Robins Center are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Price was $993, price is now $912 per person
$912
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) 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 Broad Street and Richmond Old City Hall are located nearby.
Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

3.5 out of 5
Price was $682, price is now $629 per person
$629
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesterfield Towne Center and Stony Point Fashion Park are located nearby.

3-4 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Ashland – Richmond North

Comfort Inn & Suites Ashland – Richmond North

2.5 out of 5
Price was $495, price is now $433 per person
$433
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Richmond (RIC)
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $956, price is now $813 per person
$813
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Richmond (RIC)
Ashland Studio Inn By OYO Richmond North near Kings Dominion

Ashland Studio Inn By OYO Richmond North near Kings Dominion

2.5 out of 5
Price was $499, price is now $448 per person
$448
per person
May 9 - May 13
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Richmond (RIC)
Country Inn & Suites by Radisson, Ashland - Hanover, VA

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

3 out of 5
Price was $549, price is now $479 per person
$479
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Richmond (RIC)

5-7 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $734, price is now $629 per person
$629
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $1,185, price is now $958 per person
$958
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was $1,279, price is now $1,067 per person
$1,067
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $1,067, price is now $917 per person
$917
per person
Apr 25 - May 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

Chesapeake Bay Last Minute Hotel Deals

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
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
Stay at this inn in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodville Park and White Marsh Shopping Center are located ...
Warner Hall
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
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff ...
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
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 condo in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water ...
King’s Creek Resort by Spinnaker
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Book a stay at this family-friendly hotel in Hampton. Enjoy free breakfast, room service, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Embassy Suites by Hilton Hampton Convention Center
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 6,867 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.