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Chesapeake Bay Vacation Packages

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Williamsburg

Wingate by Wyndham Williamsburg

3 out of 5
Price was $548, price is now $470 per person
$470
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Merchants Square are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,075, price is now $805 per person
$805
per person
Aug 29 - Sep 4
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 Merchants Square are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $928, price is now $702 per person
$702
per person
Aug 29 - Sep 4
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.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $882, price is now $669 per person
$669
per person
Aug 29 - Sep 4
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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $742, price is now $584 per person
$584
per person
Aug 29 - Sep 4
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 Busch Gardens Williamsburg and Merchants Square are located nearby.
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $1,209, price is now $986 per person
$986
per person
Aug 29 - Sep 4
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 Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Embassy Suites Williamsburg

Embassy Suites Williamsburg

3.5 out of 5
Price was $695, price is now $569 per person
$569
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.
The Commonwealth

The Commonwealth

4 out of 5
Price was $776, price is now $638 per person
$638
per person
Aug 31 - Sep 4
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 Richmond Raceway are located nearby.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $788, price is now $661 per person
$661
per person
Aug 29 - Sep 4
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 Busch Gardens Williamsburg and Merchants Square are located nearby.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Price was $675, price is now $570 per person
$570
per person
Aug 29 - Sep 4
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.
Comfort Inn Williamsburg Gateway

Comfort Inn Williamsburg Gateway

2.5 out of 5
Price was $630, price is now $546 per person
$546
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was $729, price is now $632 per person
$632
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Merchants Square are located nearby.

3-4 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 $642, price is now $459 per person
$459
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $822, price is now $542 per person
$542
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $806, price is now $614 per person
$614
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was $641, price is now $492 per person
$492
per person
Sep 17 - Sep 21
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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $742, price is now $584 per person
$584
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,075, price is now $805 per person
$805
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $928, price is now $702 per person
$702
per person
Aug 29 - Sep 4
found 1 day 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 $882, price is now $669 per person
$669
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)

Chesapeake Bay Last Minute Hotel Deals

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
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
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 6,854 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.