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.
The Colonies at Williamsburg
Price was CA $1,099, price is now CA $831 per person
CA $831
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,023 reviews)
This is a beautiful resort. There is a lot to do and plenty of space. The location is close to theme parks and historical sites. We recommend 100%!
Reviewed on Jun 11, 2026
Westgate Historic Williamsburg Resort
Midtown
Price was CA $1,373, price is now CA $904 per person
CA $904
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,000 reviews)
Overall the property seemed well kept visually. Our room was clean and exactly as pictured. The reason I'm not leaving a 5-star review has to do with the fact that there were lots of maintenance issues during our stay. Upon arrival, the computers were down making for a much slower check in. The staff was doing their best to accommodate despite the issue. The second day we were there the elevator was out of service, and was still out of service upon our departure the following day. The last day we were there the ice machine was out of service also. If it was just one issue or another, I would have said - things happen but it seemed like a lot of issues that weren't immediately addressed for being the middle of summer and their busy season.
Reviewed on Jun 15, 2026
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,186, price is now CA $960 per person
CA $960
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (822 reviews)
This property was a unique combination of old and new. The location in "old" Williamsburg helped us to feel like we were back in time. The property itself had great bones and was as clean as daily housekeeping could keep it. The rooms are tired however, needing carpets cleaned, furniture changed and repaired and fresh paint on the inside. Loved the vintage feel, just fine to freshen it up. The AC was great, deck and views were beautiful and the beds comfortable. Easy access because we were on the main floor and the check in process at the Williamsburg Inn was refined and made me feel very welcome!
Reviewed on Jun 12, 2026
Club Wyndham Governor’s Green
Price was CA $1,424, price is now CA $1,195 per person
CA $1,195
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (251 reviews)
Had an adult only pool totally separate from the "family" pool, which was greatly appreciated.
Did not appreciate the sales pitch upon arrival after a 6 hour drive, LOL,
Reviewed on Jun 15, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $146 per night from Jun 29 to Jun 30
CA $146
CA $162 total
Jun 29 - Jun 30
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
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 1 to Jul 2
CA $169
CA $208 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (2,514 reviews)
"Great place"
Reviewed on Jun 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 $131 per night from Jun 22 to Jun 23
CA $131
CA $189 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (3,539 reviews)
"It's a really nice property. We had a room with one king and two twin beds. The beds were comfortable, the furniture was sturdy, and there was plenty of room for two teens and two adults. Everything was nice and clean. Check in/out was quick and easy."
Reviewed on Jun 18, 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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