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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $868, price is now CA $755 per person
CA $755
per person
Aug 27 - Aug 30
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,780 reviews)
I had a very pleasant stay at this hotel. The room was clean, comfortable, and well-maintained throughout my visit. The staff were courteous, professional, and always willing to help with any questions or requests. Their friendly attitude made the experience even more enjoyable.
Reviewed on Jun 20, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,190, price is now CA $1,021 per person
CA $1,021
per person
Aug 27 - Aug 30
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,009 reviews)
Loves the lazy river and the promptness of the drivers on the property to take you places.
Reviewed on Jun 16, 2026
King’s Creek Resort by Spinnaker
Price was CA $965, price is now CA $835 per person
CA $835
per person
Aug 27 - Aug 30
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (181 reviews)
Very spacious cottages and close walking distance to all the amenities. Easy parking and safe location.
Reviewed on Jun 18, 2026
Whispering Pines by Hotel O Whitestone VA
Price was CA $972, price is now CA $856 per person
CA $856
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6.2/10 (157 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
Holiday Inn Express Williamsbrg Busch Gardens Area by IHG
Price was CA $1,161, price is now CA $1,049 per person
CA $1,049
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,245 reviews)
Room was nice. Wish the breakfast had Oj seems they were out. Other than that had a good stay.
Reviewed on Jun 19, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $142 per night from Jul 22 to Jul 23
CA $142
CA $158 total
Jul 22 - Jul 23
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"
Reviewed on Jun 20, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 5 to Jul 6
CA $174
CA $214 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,506 reviews)
"We enjoyed this property so much we tried to extend our stay but they were booked! We'll be back."
Reviewed on Jun 20, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jun 29 to Jun 30
CA $131
CA $189 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (3,499 reviews)
"Great stay"
Reviewed on Jun 20, 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.
