Search Deals on
Chesapeake Bay Vacation Packages

Build your package with 2 more options

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Kings Dominion/Doswell

Days Inn by Wyndham Kings Dominion/Doswell

2 out of 5
Price was $532, price is now $499 per person
$499
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Doswell. Enjoy an outdoor pool, a 24-hour front desk, and a business center. Popular attractions Kings Dominion and Meadow Event Park are located nearby.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $868, price is now $643 per person
$643
per person
Nov 27 - Dec 1
found 15 hours ago
Roundtrip non-stop 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.
Candlewood Suites Chester Richmond by IHG

Candlewood Suites Chester Richmond by IHG

2.5 out of 5
Price was $668, price is now $599 per person
$599
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Chester. Enjoy parking (surcharge) and a 24-hour front desk. Popular attractions Point of Rocks Park and Henricus Historical Park are located nearby.
Aloft Richmond West Short Pump

Aloft Richmond West Short Pump

3 out of 5
Price was $706, price is now $660 per person
$660
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star business-friendly hotel in Richmond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Short Pump Town Center and Elk's Lodge are located nearby.
Extended Stay America Suites Colonial Heights Fort Lee

Extended Stay America Suites Colonial Heights Fort Lee

2.5 out of 5
Price was $606, price is now $569 per person
$569
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Colonial Heights. Enjoy free parking, a 24-hour front desk, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Southpark Mall and Keystone Antique Truck and Tractor Museum are located nearby.
Courtyard by Marriott Richmond Scott’s Addition

Courtyard by Marriott Richmond Scott’s Addition

3 out of 5
Price was $818, price is now $774 per person
$774
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star business-friendly hotel in Richmond. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Moxy Richmond Downtown

Moxy Richmond Downtown

2.5 out of 5
Price was $686, price is now $655 per person
$655
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly 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 Raceway are located nearby.
MainStay Suites Prince George - Fort Gregg

MainStay Suites Prince George - Fort Gregg

2.5 out of 5
Price was $553, price is now $529 per person
$529
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Prince George. Enjoy free WiFi, free parking, and housekeeping. Popular attractions U.S. Army Women's Museum and U.S. Army Quartermaster Museum are located nearby.
Country Inn & Suites by Radisson, Richmond West at I-64, VA

Country Inn & Suites by Radisson, Richmond West at I-64, VA

3 out of 5
Price was $593, price is now $571 per person
$571
per person
Nov 27 - Dec 1
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Short Pump Town Center and Regency Square Mall are located nearby.
Red Roof Inn Doswell - Kings Dominion

Red Roof Inn Doswell - Kings Dominion

2 out of 5
Price was $524, price is now $505 per person
$505
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Doswell. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kings Dominion and Meadow Event Park are located nearby.
Courtyard by Marriott Richmond Northwest

Courtyard by Marriott Richmond Northwest

3 out of 5
Price was $687, price is now $664 per person
$664
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star hotel in Richmond. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Short Pump Town Center and Elk's Lodge are located nearby.
Residence Inn by Marriott Richmond Downtown

Residence Inn by Marriott Richmond Downtown

3 out of 5
Price was $789, price is now $774 per person
$774
per person
Nov 27 - Dec 1
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3-star business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions Broad Street and Richmond Raceway are located nearby.

3-4 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $829, price is now $606 per person
$606
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $868, price is now $643 per person
$643
per person
Nov 27 - Dec 1
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $798, price is now $644 per person
$644
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
Price was $783, price is now $637 per person
$637
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)

5-7 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
Price was $803, price is now $576 per person
$576
per person
Nov 28 - Dec 5
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $997, price is now $684 per person
$684
per person
Nov 28 - Dec 5
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
Price was $875, price is now $628 per person
$628
per person
Nov 28 - Dec 5
found 18 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 $1,061, price is now $765 per person
$765
per person
Nov 28 - Dec 5
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)

Chesapeake Bay Last Minute Hotel Deals

Onley Inn

Onley Inn

2 out of 5
25297 Lankford Hwy, Onley, VA
Stay at this hotel in Onley. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Onley Inn
Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
2800 Shore Drive, Virginia Beach, VA
Stay at this 4-star business-friendly hotel in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the restaurant and the ...
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Crown Inn Motel

Crown Inn Motel

2 out of 5
7833 George Washington Memorial Highway, Yorktown, VA
Stay at this motel in Yorktown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hampton Roads Harley-Davidson and Chisman Creek ...
Crown Inn Motel
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Stay at this 3-star 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
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Book a stay at this business-friendly hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn Newport News - Hampton I-64
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
Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

3 out of 5
401 Butler Farm Rd, Hampton, VA
Book a stay at this business-friendly hotel in Hampton. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Sonesta Simply Suites Hampton
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
191 Cottage Cove Lane, Williamsburg, VA
Stay at this 4.5-star 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
See all 6,712 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.