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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 $916, price is now CA $797 per person
CA $797
per person
Aug 1 - Aug 4
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,756 reviews)
Make sure you’re not in and out and you have time to enjoy all the amenities around the property. A lot of things to do.
Reviewed on Jun 12, 2026

King’s Creek Resort by Spinnaker
Price was CA $1,428, price is now CA $1,208 per person
CA $1,208
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (175 reviews)
We had a small issue when we got to our first unit. Apparently housekeeping had reported the air conditioning wasn’t working, but we were still checked into the unit anyway and we were met by the maintenance tech when we were unpacking our car. We switched to a second unit which was perfect, except the phone in the unit didn’t work, so we had to call from ours cell phones, which wasn’t that big of a deal. The paper they gave us at check in with hours of the activity center (and on the QR code you scan in your unit) were incorrect, we walked in 10 min before 6 and the young lady told us, yeah we have been trying to communicate with them, but I’ve only been here 2 weeks.
All in all, this is the 2nd time I’ve stayed here and honestly haven’t had any true issues that won’t bring me back the next time I come to Williamsburg. Staff is super friendly, pools are clean, and the units are spacious. I will say, the pull out side beds need some kind of an update, my oldest wouldn’t even sleep on the bed part and just slept on the actual sofa for the few days we were there.
Reviewed on Jun 7, 2026

Whispering Pines by Hotel O Whitestone VA
Price was CA $1,044, price is now CA $899 per person
CA $899
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.2/10 (155 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

Wyndham Garden Williamsburg Busch Gardens Area
Price was CA $1,131, price is now CA $993 per person
CA $993
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
7/10 Good! (533 reviews)
Breakfast was out of some food by 0830 and no regular coffee. Televisions had few channels.
Reviewed on Jun 10, 2026

Kingsmill Resort
Kingsmill
Price was CA $1,515, price is now CA $1,337 per person
CA $1,337
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,009 reviews)
There was a pool adjacent to our room which was a huge bonus arriving on hot day!! Wish we could have stayed longer!!
Reviewed on Jun 7, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $145 per night from Jun 21 to Jun 22
CA $145
CA $162 total
Jun 21 - Jun 22
includes taxes & fees
7.2/10 Good! (707 reviews)
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."
Reviewed on Jun 9, 2026

Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Jun 28 to Jun 29
CA $156
CA $174 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (768 reviews)
"Everything was great. Everyone was polite."
Reviewed on Jun 11, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Jun 14 to Jun 15
CA $168
CA $207 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (2,495 reviews)
"Our stay was a great experience and we didn't have any issues. The staff we encountered were friendly and attentive. The apartment was spacious and suit d out family well. The only thing I would recommend would be a few updates and repairs (out of date appliances, chipped/loose tiles) as well as ..."
Reviewed on Jun 12, 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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