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Chesapeake Bay Vacation Packages

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 $495, price is now $465 per person
$465
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 1 day 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.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Price was $821, price is now $732 per person
$732
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 4-star 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 Broad Street and Richmond Raceway are located nearby.
Quirk Hotel Richmond

Quirk Hotel Richmond

4 out of 5
Price was $921, price is now $861 per person
$861
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 4-star business-friendly hotel in Richmond. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway 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 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 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.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Price was $785, price is now $757 per person
$757
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 4-star 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 Richmond Raceway are located nearby.
Red Roof Inn Doswell - Kings Dominion

Red Roof Inn Doswell - Kings Dominion

2 out of 5
Price was $487, price is now $470 per person
$470
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.
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 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 breakfast, free WiFi, and a 24-hour fitness center. Popular attractions Broad Street and Richmond Raceway are located nearby.
Country Inn & Suites by Radisson, Ashland - Hanover, VA

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

3 out of 5
Price was $592, price is now $580 per person
$580
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 Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions James River Cellars Winery and Lavender Fields Herb Farm are located nearby.
Richmond Marriott

Richmond Marriott

3.5 out of 5
Price was $762, price is now $749 per person
$749
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this 3.5-star business-friendly hotel in Richmond. Enjoy free WiFi, 2 bars/lounges, 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.
Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

2.5 out of 5
Price was $591, price is now $591 per person
$591
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 business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kings Dominion and Banks Tennis Center are located nearby.
Courtyard by Marriott Richmond Downtown

Courtyard by Marriott Richmond Downtown

3 out of 5
Price was $767, price is now $767 per person
$767
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 in our reviews. 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.
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 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 $746, price is now $648 per person
$648
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Williamsburg Lodge, Autograph Collection

Williamsburg Lodge, Autograph Collection

4 out of 5
Colonial Williamsburg
Price was $1,335, price is now $1,134 per person
$1,134
per person
Dec 6 - Dec 9
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was $1,020, price is now $868 per person
$868
per person
Dec 6 - Dec 9
found 18 hours 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 1 day 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 1 day 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 1 day 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 1 day 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 6,690 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.