Search Deals on
Gwynn 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

A pier extending into calm waters at sunset with a clear sky.

Gwynn
Virginia
United States of America
North America
Hotwire.com

Gwynn Flight + Hotel Packages

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

Wingate by Wyndham Richmond Short Pump

3 out of 5

Price was $539, price is now $439 per person

$439

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Islip (ISP) 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 Short Pump Village are located nearby.

The Colonies at Williamsburg

3 out of 5

Price was $655, price is now $521 per person

$521

per person

Dec 24 - Dec 27

found 4 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Had a great time with my family because it was so clean and cozy.

Reviewed on Nov 8, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5

Price was $808, price is now $651 per person

$651

per person

Dec 24 - Dec 27

found 4 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Okay but not great.

Reviewed on Nov 4, 2026

Hyatt Select Richmond/Chester

3 out of 5

Price was $795, price is now $649 per person

$649

per person

Jan 31 - Feb 6

found 19 hours ago

Roundtrip flight included

New York (JFK) 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.

Club Wyndham Governor’s Green

3 out of 5

Price was $776, price is now $659 per person

$659

per person

Dec 24 - Dec 27

found 4 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Excellent resort. Plenty of amenities in a great location!

Reviewed on Nov 9, 2026

Wedmore Place

3.5 out of 5

Price was $812, price is now $694 per person

$694

per person

Dec 24 - Dec 27

found 4 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

Book a stay at this boutique hotel in Williamsburg. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.

Included breakfast is a continental breakfast.

Reviewed on Nov 9, 2026

Holiday Inn Express Hotel & Suites Richmond North Ashland by IHG

2.5 out of 5

Price was $672, price is now $574 per person

$574

per person

Jan 31 - Feb 6

found 19 hours ago

Roundtrip flight included

New York (JFK) to Richmond (RIC)

Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Kings Dominion and Banks Tennis Center are located nearby.

The Commonwealth

4 out of 5

Price was $750, price is now $642 per person

$642

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip flight included

Islip (ISP) 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 Altria Theater are located nearby.

Reviewed on Nov 9, 2026