Gloucester Vacation Packages
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Your Gloucester Vacation
From its coastal scenery to its rich history and beyond, there's loads to like about Gloucester. Discover the wonders of this captivating city with a Gloucester vacation package that's made for you. Eager to do a bit of sightseeing? A trip to Gloucester isn't complete without checking out Middle Peninsula State Park, Gloucester Museum of History and other major attractions. Your Gloucester vacation is clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
Top Gloucester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Whispering Pines by Hotel O Whitestone VA
Price was CA $1,198, price is now CA $981 per person
CA $981
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.2/10 (154 reviews)
Not bad for a mid century motel. Room was small but I would call it european. Bathroom dated but clean. Needed a light bulb in shower, lampshade for table lamp, and smoke detector hooked up. When we checked in we had to air it out because of the sanitation smell but other than that I would stay again.
Reviewed on Oct 13, 2025
Kingsmill Resort
Kingsmill
Price was CA $1,798, price is now CA $1,358 per person
CA $1,358
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
Beautiful resort. The Marina was beautiful and our room was incredible.
Reviewed on May 12, 2026
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,313, price is now CA $1,107 per person
CA $1,107
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,001 reviews)
Breakfast was delicious, the rooms were clean, the beds were extremely comfortable, the we really enjoyed the restaurant for a light meal
Reviewed on May 17, 2026
Kings Creek Plantation by TripForth
Price was CA $1,993, price is now CA $1,687 per person
CA $1,687
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (42 reviews)
This was probably the best property that I've stayed at, maybe ever. I had a family of 8 and the two apartments that we shared were perfect. I will be staying here again
Reviewed on Jul 13, 2025
Holiday Inn Express Williamsbrg Busch Gardens Area by IHG
Price was CA $1,725, price is now CA $1,461 per person
CA $1,461
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,251 reviews)
Property was very clean with a large room and comfortable bed. Very friendly staff and good free breakfast. In a nice area and accessible to many restaurants and attractions.
Reviewed on May 14, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (696 reviews)
They didn't clean the room every day.
Reviewed on May 8, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from May 31 to Jun 1
CA $109
CA $140 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (2,402 reviews)
There was no hot water in my unit and it took hours before i could shower
Reviewed on May 17, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 29 to May 30
CA $127
CA $184 total
May 29 - May 30
includes taxes & fees
9/10 Wonderful! (3,469 reviews)
Nothing
Reviewed on May 17, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
