Search Deals onGloucester Vacation Packages
Gloucester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Turnpike Motel Richmond VA by Hotel O US 60
Price was $613, price is now $498 per person
$498
per person
Oct 23 - Oct 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Maymont Park and Broad Street are located nearby.
Wedmore Place
Save 100% on your flight
Price was $1,043, price is now $695 per person
$695
per person
Oct 23 - Oct 28
found 1 day 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.
The help was extremely friendly and helpful. Pool is not fancy but at the perfect temperature. Floors are old and creaky but add to the overall atmosphere of the place. Daily breakfast was more than enough to start the day.
Reviewed on Aug 15, 2026
Kingsmill Resort
Price was $1,075, price is now $746 per person
$746
per person
Oct 18 - Oct 23
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 Williamsburg Winery are located nearby.
Great experience
Reviewed on Aug 17, 2026
Griffin Hotel, an official Colonial Williamsburg Hotel
Save 100% on your flight
Price was $1,227, price is now $852 per person
$852
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Water Country USA are located nearby.
Club Wyndham Governor’s Green
Price was $1,004, price is now $786 per person
$786
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Richmond Marriott Short Pump
Price was $1,009, price is now $835 per person
$835
per person
Oct 23 - Oct 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Glen Allen. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Short Pump Town Center and Elk's Lodge are located nearby.
King’s Creek Resort by Spinnaker
Price was $639, price is now $534 per person
$534
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
It was amazing g I had a great time.the only that was not working was the garbage disposal
Reviewed on Aug 18, 2026
A house full of steel balls and games
Price was $596, price is now $501 per person
$501
per person
Oct 23 - Oct 28
found 1 hour ago
Roundtrip flight included
Boston (BOS) 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 Maymont Park are located nearby.
Thanks so much for the wonderful stay!
Reviewed on Aug 6, 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.
Tue, Sep 15 - Thu, Sep 17
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$75 Roundtrip, found 16 hours ago
$75
Roundtrip
found 16 hours ago
Wed, Oct 28 - Sat, Nov 7
MCO
Orlando Intl.
ORF
Norfolk Intl.
$113 Roundtrip, found 16 hours ago
$113
Roundtrip
found 16 hours ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
RIC
Richmond Intl.
$126 Roundtrip, found 2 days ago
$126
Roundtrip
found 2 days ago
Sat, Oct 24 - Sat, Oct 31
LGA
LaGuardia
ORF
Norfolk Intl.
$174 Roundtrip, found 16 hours ago
$174
Roundtrip
found 16 hours ago
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