Search Deals onGloucester Vacation Packages
Gloucester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Richmond Short Pump
Price was $279, price is now $237 per person
$237
per person
Dec 4 - Dec 6
found 2 hours ago
Roundtrip flight included
Hartford (BDL) 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.
Checkin staff was great. Couldn't use A/C in room because of noise it made. Glad it was cool outside and fan worked. One Elevator didn't work. The one that did was very dirty. Halls and doors need freshening up. Parking great. Location good.
Reviewed on Oct 19, 2026
The Commonwealth
Price was $800, price is now $550 per person
$550
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Overall impression was an old bldg made newish Narrow halls, tiny elevators, street in front blocked off, no free guest parking and nice, helpful extremely weird looking staff at check- out Beds were comfortable and 2 flat screen tvs were a Plus Probably would not stay there again!
Reviewed on Oct 19, 2026
Kingsmill Resort
Price was $843, price is now $680 per person
$680
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Water Country USA are located nearby.
Nice room, good restaurants and pools.
Reviewed on Oct 18, 2026
Club Wyndham Governor’s Green
Price was $936, price is now $775 per person
$775
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Club Wyndham Kingsgate
Price was $774, price is now $655 per person
$655
per person
Nov 28 - Dec 3
found 12 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Book a stay at this family-friendly resort in Williamsburg. Enjoy free WiFi, free parking, 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.
Kings Creek Plantation by TripForth
Price was $1,261, price is now $1,079 per person
$1,079
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this vacation home in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Beautiful property!!
Reviewed on Aug 2, 2026
Omni Richmond Hotel
Price was $357, price is now $311 per person
$311
per person
Dec 4 - Dec 6
found 2 hours ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Wedmore Place
Price was $911, price is now $801 per person
$801
per person
Nov 27 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Islip (ISP) 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 Historic Jamestowne are located nearby.
Great place to stay while visiting Williamsburg and the rest of the area. Williamsburg Winery on site was great. Room was nice as well. The decor was cool. Bathroom and TV were a little dated but we never used the TV. Bathroom in our particular room could use some updating, but nothing that took away from the overall experience. It has the feel of a place that could be really awesome with some freshening.
Reviewed on Oct 20, 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.
$48 Roundtrip, just found
$48
Roundtrip
just found
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
ORF
Norfolk Intl.
$119 Roundtrip, found 5 hours ago
$119
Roundtrip
found 5 hours ago
Tue, Nov 17 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Wed, Dec 9 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
RIC
Richmond Intl.
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
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