Search Deals on
Chesapeake Bay Vacation Packages

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Price was $688, price is now $526 per person
$526
per person
Aug 28 - Sep 3
found 1 day 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 Merchants Square are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Save 100% on your flight
Price was $1,054, price is now $693 per person
$693
per person
Aug 19 - Aug 26
found 1 day 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 Maymont Park are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $992, price is now $659 per person
$659
per person
Aug 28 - Sep 3
found 1 day 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 Merchants Square are located nearby.
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $1,316, price is now $983 per person
$983
per person
Aug 28 - Sep 3
found 1 day 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 Water Country USA and Busch Gardens Williamsburg are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,126, price is now $846 per person
$846
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Water Country USA are located nearby.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Price was $1,889, price is now $1,452 per person
$1,452
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury hotel in Williamsburg. Enjoy an outdoor pool, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Water Country USA and Busch Gardens Williamsburg are located nearby.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $779, price is now $604 per person
$604
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly motel 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 Water Country USA and Busch Gardens Williamsburg are located nearby.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $842, price is now $660 per person
$660
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Merchants Square are located nearby.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Price was $804, price is now $632 per person
$632
per person
Aug 19 - Aug 26
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 Elk's Lodge are located nearby.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Price was $960, price is now $756 per person
$756
per person
Aug 19 - Aug 26
found 1 day 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 Maymont Park are located nearby.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $862, price is now $680 per person
$680
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this 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 Water Country USA and Busch Gardens Williamsburg are located nearby.

3-4 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Motel 6 Sandston, VA - Richmond, Va

Motel 6 Sandston, VA - Richmond, Va

2 out of 5
Price was $435, price is now $423 per person
$423
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $707, price is now $595 per person
$595
per person
Aug 12 - Aug 16
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Fairfield Inn By Marriott Richmond Chester

Fairfield Inn By Marriott Richmond Chester

3 out of 5
Price was $543, price is now $533 per person
$533
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Short Pump
Price was $889, price is now $874 per person
$874
per person
Aug 12 - Aug 16
found 23 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.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $992, price is now $659 per person
$659
per person
Aug 28 - Sep 3
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 $1,054, price is now $693 per person
$693
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $1,316, price is now $983 per person
$983
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,126, price is now $846 per person
$846
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Quality Inn & Suites Exmore - Eastern Shore

Quality Inn & Suites Exmore - Eastern Shore

2.5 out of 5
2543 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 helpful staff and the clean rooms ...
Quality Inn & Suites Exmore - Eastern Shore
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
Cape Charles Milestone Lodge

Cape Charles Milestone Lodge

23054 Lankford Hwy. Cape Charles VA
Stay at this motel in Cape Charles. Enjoy free WiFi, free parking, and concierge services. Popular attractions Cape Charles Beach and Cape Charles Museum & Welcome ...
Cape Charles Milestone Lodge
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
Book a stay at this beach hotel in Irvington. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Steamboat Era Museum and Historic ...
The Tides Inn
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
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
See all 6,874 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.