Search Deals on
Chesapeake Bay Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

Chesapeake Bay
United States of America
North America
Hotwire.com

Chesapeake Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

A house full of steel balls and games

2.5 out of 5

Save 100% on your flight

Price was $263, price is now $177 per person

$177

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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 Broad Street are located nearby.

Westgate Historic Williamsburg Resort

3.5 out of 5

Save 100% on your flight

Price was $434, price is now $217 per person

$217

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 3.5-star family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, 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.

The Colonies at Williamsburg

3 out of 5

Save 100% on your flight

Price was $425, price is now $274 per person

$274

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 3-star 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 Bowlero Williamsburg are located nearby.

Barsala At Sphere Apartments

3.5 out of 5

Save 100% on your flight

Price was $786, price is now $507 per person

$507

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 3.5-star aparthotel in Richmond. Enjoy free WiFi, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Broad Street and Richmond Raceway are located nearby.

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5

Save 100% on your flight

Price was $886, price is now $583 per person

$583

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 5-star 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 Busch Gardens Williamsburg and Water Country USA are located nearby.

Linden Row Inn

3 out of 5

Save 100% on your flight

Price was $536, price is now $361 per person

$361

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 3-star 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.

Williamsburg Lodge, Autograph Collection

4 out of 5

Save 100% on your flight

Price was $405, price is now $275 per person

$275

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 4-star luxury hotel in Williamsburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5

Save 100% on your flight

Price was $355, price is now $243 per person

$243

per person

Sep 4 - Sep 7

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Stay at this 3-star spa hotel in Williamsburg. Enjoy 3 outdoor pools, a full-service spa, and a golf course. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.