Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Patriots Inn
Price was $631, price is now $492 per person
$492
per person
Sep 10 - Sep 14
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly aparthotel 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.
Clean room. Nice pool! Kids loved the game room. Good location to Water Country and Busch Gardens.
Reviewed on Aug 10, 2026
Wedmore Place
Price was $1,009, price is now $692 per person
$692
per person
Oct 23 - Oct 28
found 19 hours 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 Williamsburg Winery are located nearby.
Kingsmill Resort
Price was $821, price is now $621 per person
$621
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Richmond (RIC)
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Winery are located nearby.
We did not use any of the amenities.
Only issue was no hair dryer in room
Reviewed on Aug 9, 2026
Super 8 by Wyndham Hull Street Midlothian / Richmond Area
Price was $899, price is now $691 per person
$691
per person
Sep 14 - Sep 18
found 24 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Midlothian. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rockwood Park and Bowl America Southwest are located nearby.
Staff was nice and patient
Reviewed on Aug 4, 2026
Super 8 by Wyndham Chester/Richmond Area
Price was $858, price is now $661 per person
$661
per person
Sep 14 - Sep 18
found 24 hours ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Parker's Battery Park and The Lazy Daisy are located nearby.
Bad
Reviewed on Aug 9, 2026
The Commonwealth
Price was $828, price is now $643 per person
$643
per person
Oct 16 - Oct 19
found 15 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
The Colonies at Williamsburg
Price was $920, price is now $718 per person
$718
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Beautiful for family fun!
Reviewed on Aug 9, 2026
Vaiden Inn
Price was $720, price is now $563 per person
$563
per person
Sep 17 - Sep 21
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Stay at this guesthouse in New Kent. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Heritage Public Library and Cumberland Marsh Natural Area Preserve are located nearby.
Chester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Aug 11 - Sun, Aug 16
MCO
Orlando Intl.
RIC
Richmond Intl.
$91 Roundtrip, found 4 days ago
$91
Roundtrip
found 4 days ago
Tue, Oct 6 - Tue, Oct 13
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$168 Roundtrip, found 9 hours ago
$168
Roundtrip
found 9 hours ago
Mon, Oct 5 - Mon, Oct 5
EWR
Newark Liberty Intl. Airport
RIC
Richmond Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Sat, Aug 22 - Wed, Aug 26
BOS
Logan Intl.
RIC
Richmond Intl.
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
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