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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 $408, price is now $349 per person
$349
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $966, price is now $815 per person
$815
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Jamestown Settlement are located nearby.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $996, price is now $850 per person
$850
per person
May 27 - May 31
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
OYO Palm Leaf Motel

OYO Palm Leaf Motel

2.5 out of 5
Price was $530, price is now $452 per person
$452
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Ashland. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Kings Dominion and Banks Tennis Center are located nearby.
Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Price was $715, price is now $633 per person
$633
per person
May 28 - Jun 1
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Richmond. Enjoy free WiFi, a full-service spa, and 2 restaurants. 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.
Woodspring Suites Ashland - Richmond North

Woodspring Suites Ashland - Richmond North

2.5 out of 5
Price was $439, price is now $390 per person
$390
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions James River Cellars Winery and Lavender Fields Herb Farm are located nearby.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Price was $618, price is now $477 per person
$477
per person
Jun 4 - Jun 8
found 14 hours 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 Elk's Lodge are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Price was $743, price is now $596 per person
$596
per person
Jun 4 - Jun 8
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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 Raceway are located nearby.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Price was $726, price is now $586 per person
$586
per person
Jun 4 - Jun 8
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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 Richmond Raceway 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 $474, price is now $390 per person
$390
per person
Jun 4 - Jun 8
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free WiFi, free parking, and room service. Popular attractions Broad Street and Putt-Putt Fun Center 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 $466, price is now $385 per person
$385
per person
Jun 4 - Jun 8
found 14 hours ago
Roundtrip flight included
Boston (BOS) 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 South of the James Market are located nearby.
Linden Row Inn

Linden Row Inn

3 out of 5
Price was $890, price is now $739 per person
$739
per person
Jun 4 - Jun 8
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this historic hotel in Richmond. Enjoy free WiFi, a 24-hour front desk, and 2 meeting rooms. Our guests praise the helpful staff and the clean rooms 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.
Richmond Marriott Short Pump

Richmond Marriott Short Pump

3 out of 5
Price was $731, price is now $547 per person
$547
per person
Jun 11 - Jun 14
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $1,692, price is now $1,184 per person
$1,184
per person
Jun 11 - Jun 14
found 18 hours ago
Roundtrip flight included
Boston (BOS) 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 $752, price is now $548 per person
$548
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was $873, price is now $647 per person
$647
per person
Jun 11 - Jun 14
found 13 hours ago
Roundtrip 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 $530, price is now $514 per person
$514
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $916, price is now $734 per person
$734
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $851, price is now $707 per person
$707
per person
Jun 7 - Jun 12
found 21 hours ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $682, price is now $604 per person
$604
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 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 restaurant and the helpful staff ...
Wyndham Virginia Beach Oceanfront
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
Hyatt Place Virginia Beach / Oceanfront
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 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
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
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
See all 6,924 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.