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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 $464, price is now $428 per person
$428
per person
Sep 24 - Sep 28
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Doswell. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Kings Dominion and Meadow Event Park 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 $679, price is now $560 per person
$560
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip non-stop 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 Maymont Park 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 $656, price is now $556 per person
$556
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop 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 Maymont Park are located nearby.
Delta Hotels by Marriott Richmond Downtown

Delta Hotels by Marriott Richmond Downtown

3.5 out of 5
Price was $1,077, price is now $946 per person
$946
per person
Oct 14 - Oct 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Maymont Park are located nearby.
Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
Price was $763, price is now $677 per person
$677
per person
Oct 14 - Oct 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Point of Rocks Park and Henricus Historical Park are located nearby.
Best Western PLUS Executive Hotel

Best Western PLUS Executive Hotel

2.5 out of 5
Price was $665, price is now $599 per person
$599
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip non-stop 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 Maymont Park and Richmond Raceway are located nearby.
Brentwood Inn Richmond South

Brentwood Inn Richmond South

2 out of 5
Price was $548, price is now $501 per person
$501
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Richmond (RIC)
Stay at this motel in Richmond. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions The Lazy Daisy and Henricus Historical Park are located nearby.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Price was $747, price is now $685 per person
$685
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly B&B in Richmond. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Richmond Raceway and Maymont Park are located nearby.
Candlewood Suites Richmond North Glen Allen by IHG

Candlewood Suites Richmond North Glen Allen by IHG

2.5 out of 5
Price was $606, price is now $559 per person
$559
per person
Oct 3 - Oct 10
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Glen Allen. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Richmond Raceway and The Crossings Golf Club are located nearby.
The Boulevard Inn

The Boulevard Inn

4 out of 5
Price was $1,265, price is now $1,170 per person
$1,170
per person
Oct 1 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Richmond (RIC)
Stay at this B&B in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,006, price is now $715 per person
$715
per person
Oct 13 - Oct 17
found 9 hours ago
Roundtrip flight included
Dallas (DFW) 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 Williamsburg Winery are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $740, price is now $550 per person
$550
per person
Oct 14 - Oct 19
found 18 hours 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.

3-4 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Turnpike Motel Richmond VA by Hotel O US 60

Turnpike Motel Richmond VA by Hotel O US 60

2.5 out of 5
Midlothian
Price was $598, price is now $540 per person
$540
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Richmond (RIC)
Quirk Hotel Richmond

Quirk Hotel Richmond

4 out of 5
Downtown Richmond
Price was $973, price is now $859 per person
$859
per person
Oct 13 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $820, price is now $724 per person
$724
per person
Oct 13 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
Price was $675, price is now $609 per person
$609
per person
Oct 13 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)

5-7 Night Vacations in Chesapeake Bay

Price found within the past 48 hours. Click for updated prices.
Eagle Inn by Hotel O Richmond Midlothian Turnpike

Eagle Inn by Hotel O Richmond Midlothian Turnpike

2.5 out of 5
Midlothian
Price was $656, price is now $556 per person
$556
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Turnpike Motel Richmond VA by Hotel O US 60

Turnpike Motel Richmond VA by Hotel O US 60

2.5 out of 5
Midlothian
Price was $679, price is now $560 per person
$560
per person
Oct 3 - Oct 10
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was $961, price is now $816 per person
$816
per person
Oct 14 - Oct 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was $946, price is now $830 per person
$830
per person
Oct 14 - Oct 19
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)

Chesapeake Bay Last Minute Hotel Deals

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
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
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
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. ...
Wyndham Virginia Beach Oceanfront
Quality Inn Kilmarnock

Quality Inn Kilmarnock

2.5 out of 5
599 N Main St Kilmarnock VA
Book a stay at this business-friendly hotel in Kilmarnock. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Kilmarnock
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
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.