Search Deals onGloucester Vacation Packages
Gloucester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Kings Dominion/Doswell
Price was $618, price is now $544 per person
$544
per person
Dec 27 - Jan 3
found 4 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Wingate by Wyndham Richmond Short Pump
Price was $952, price is now $739 per person
$739
per person
Dec 19 - Dec 26
found 16 hours ago
Roundtrip non-stop 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.
Kingsmill Resort
Price was $655, price is now $573 per person
$573
per person
Dec 27 - Dec 30
found 18 hours ago
Roundtrip flight included
New York (NYC) 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 Merchants Square are located nearby.
Hyatt Select Richmond/Chester
Price was $987, price is now $866 per person
$866
per person
Dec 19 - Dec 26
found 16 hours ago
Roundtrip non-stop flight included
Islip (ISP) 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.
Hyatt House Richmond / Short Pump
Price was $998, price is now $893 per person
$893
per person
Dec 19 - Dec 26
found 16 hours ago
Roundtrip non-stop 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.
Holiday Inn Express Hopewell - Fort Lee by IHG
Price was $913, price is now $819 per person
$819
per person
Dec 19 - Dec 26
found 16 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Richmond (RIC)
Stay at this hotel in Hopewell. Enjoy free breakfast, free WiFi, and a health club. Our guests praise the helpful staff in our reviews. Popular attractions U.S. Army Women's Museum and U.S. Army Quartermaster Museum are located nearby.
Hyatt Place Richmond/Arboretum
Price was $935, price is now $842 per person
$842
per person
Dec 19 - Dec 26
found 16 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesterfield Towne Center and Rockwood Park are located nearby.
Country Inn & Suites by Radisson, Ashland - Hanover, VA
Price was $863, price is now $777 per person
$777
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 James River Cellars Winery and Lavender Fields Herb Farm are located nearby.
The staff is very helpful and friendly. Our room, and the entire property, was very clean and well maintained. Will definitely stay here again.
Reviewed on Nov 12, 2026
Gloucester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Gloucester 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.
Wed, Dec 2 - Wed, Dec 16
MCO
Orlando Intl.
RIC
Richmond Intl.
$88 Roundtrip, found 15 hours ago
$88
Roundtrip
found 15 hours ago
Fri, Dec 11 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$149 Roundtrip, just found
$149
Roundtrip
just found
Thu, Jan 7 - Tue, Jan 12
MCO
Orlando Intl.
ORF
Norfolk Intl.
$201 Roundtrip, found 1 hour ago
$201
Roundtrip
found 1 hour ago
Wed, Dec 2 - Wed, Dec 16
LGA
LaGuardia
RIC
Richmond Intl.
$208 Roundtrip, found 6 hours ago
$208
Roundtrip
found 6 hours ago
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