
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.

Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA
Price was CA $961, price is now CA $867 per person
CA $867
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
7.6/10 Good! (178 reviews)
The staff was friendly and helpful, rooms are obviously older, not the cleanest we’ve stayed in. The hallways were hot, but rooms were thankfully cool. The elevator was incredibly slow, constantly beeping. Pool was ok, but water was pretty cloudy. Fine for a couple nights, but not what I expected for the price.
Reviewed on Jul 6, 2026

Kingsmill Resort
Kingsmill
Price was CA $1,675, price is now CA $1,285 per person
CA $1,285
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
This resort had everything you would need that was kid, friendly pool, food and history, all in one.
Reviewed on Jul 6, 2026

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort
Price was CA $1,358, price is now CA $1,108 per person
CA $1,108
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (457 reviews)
Fantastic stay for my family! Very comfortable.
Reviewed on Jun 30, 2026


King’s Creek Resort by Spinnaker
Price was CA $1,226, price is now CA $1,056 per person
CA $1,056
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (200 reviews)
⭐⭐⭐⭐⭐
We had a wonderful stay at this resort! The staff was incredibly friendly, welcoming, knowledgeable, and always willing to help with anything we needed. From check-in to check-out, everyone made us feel like valued guests.
Our accommodations were clean, spacious, and very comfortable. The property itself was well maintained, with multiple pools and playgrounds that were spotless and provided plenty of options for both relaxation and family fun.
The only downsides to our stay were being invited to what was described as a 90-minute presentation that ended up lasting about 2½ hours, and having an issue with our room door on the second day. The battery in the door lock needed to be replaced, which left us locked out of our room for about 45 minutes while it was being fixed.
Despite those inconveniences, the overall experience was excellent. The beautiful property, outstanding staff, and great amenities far outweighed the negatives. We would definitely stay here again and recommend this resort to others looking for a relaxing, family friendly and enjoyable vacation.
Reviewed on Jul 3, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $148 per night from Jul 19 to Jul 20
CA $148
CA $164 total
Jul 19 - Jul 20
includes taxes & fees
7.2/10 Good! (712 reviews)
"My room smelled of mold and mildew.. My bedding felt damp. Staff quickly exchanged linens, but next night, those linens felt damp also. Room smelled moldy the entire trip. Other then that it was fair."
Reviewed on Jul 6, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Aug 4 to Aug 5
CA $170
CA $210 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,582 reviews)
"Whenever my family and I visit the Williamsburg area, Vacation Village is always our first choice. We love how clean and well-maintained the apartments are, and the peaceful, quiet atmosphere makes it easy to relax.One of our favorite features is the swimming pool, along with all the other amenities ..."
Reviewed on Jul 7, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $132 per night from Jul 20 to Jul 21
CA $132
CA $190 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (3,572 reviews)
"Clean, quiet and beautiful place to relax and a perfect getaway. I would definitely come back."
Reviewed on Jul 6, 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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