
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 Commonwealth
Downtown Richmond
Price was CA $1,190, price is now CA $1,053 per person
CA $1,053
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
8.8/10 Excellent! (1,358 reviews)
Great location. You're an easy drive or walk to anything you want to do in Richmond. The suites are enormous and worked perfectly for our family of 3.
Staff is friendly and easy to deal with.
Valet parking is convenient and the overall stay was excellent.
Will definitely stay here again
Thanks!
Reviewed on Jun 5, 2026

Kingsmill Resort
Kingsmill
Price was CA $1,716, price is now CA $1,421 per person
CA $1,421
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (1,003 reviews)
Beautiful and peaceful gem! The water view is amazing. We loved everything about our stay there. Will definitely go back soon!
Reviewed on May 31, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,237, price is now CA $1,054 per person
CA $1,054
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (1,737 reviews)
Very close to everything.
Reviewed on Jun 8, 2026

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG
Price was CA $1,302, price is now CA $1,149 per person
CA $1,149
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
9.2/10 Wonderful! (1,228 reviews)
The room was comfortable and clean with a very comfortable bed. The breakfast and coffee were great! The staff was so friendly and accommodating, and it is very convenient to the historical triangle.
Reviewed on Jun 5, 2026

King’s Creek Resort by Spinnaker
Price was CA $1,301, price is now CA $1,156 per person
CA $1,156
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (169 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
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $139 per night from Jul 7 to Jul 8
CA $139
CA $155 total
Jul 7 - Jul 8
includes taxes & fees
7.2/10 Good! (706 reviews)
"There was no running water when we checked in. We were told it would be fixed in 3 hours. We left for a few hours to have dinner. When we returned, there was cold water only. We called the desk. Someone said the hot water would be repaired the next day. So no showers for us, and no one ..."
Reviewed on Jun 3, 2026

Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 8 to Jul 9
CA $162
CA $180 total
Jul 8 - Jul 9
includes taxes & fees
9.2/10 Wonderful! (766 reviews)
"The rooms were very nice and I really enjoyed my stay."
Reviewed on May 27, 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 11 to Jun 12
CA $168
CA $207 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (2,468 reviews)
"Room was clean. Some lights didn't work. Hot tub was broken and according to others has been for years. The arcade , change machine was out of order so the kids were disappointed. Be prepared for a wait at check in . Staff is friendly when you finally reach the counter in all honesty felt they were ..."
Reviewed on Jun 8, 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.







