
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.

Whispering Pines by Hotel O Whitestone VA
Price was CA $1,443, price is now CA $1,110 per person
CA $1,110
per person
Jun 26 - Jul 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.2/10 (154 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 $1,819, price is now CA $1,519 per person
CA $1,519
per person
Jun 26 - Jul 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,251 reviews)
Clean room, breakfast is ok.
Reviewed on May 17, 2026

King’s Creek Resort by Spinnaker
Price was CA $1,734, price is now CA $1,454 per person
CA $1,454
per person
Jun 26 - Jul 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (160 reviews)
Very clean cottage. Staff was great and the amenities. A major plus, a Target Department store is within a quarter mile of the entrance.
Reviewed on May 19, 2026

Wyndham Garden Williamsburg Busch Gardens Area
Price was CA $1,357, price is now CA $1,183 per person
CA $1,183
per person
Jun 26 - Jul 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
7/10 Good! (507 reviews)
Outstanding customer service and breakfast menu.
Reviewed on May 15, 2026

Warner Hall
Price was CA $2,351, price is now CA $2,060 per person
CA $2,060
per person
Jun 26 - Jul 3
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
10/10 Exceptional! (28 reviews)
I can’t say enough good things about The Inn At Warner Hall. The staff, the rooms, the food, the scenery - we spent 3 nights for a getaway and didn’t want to leave. We’re already trying to find the next time we can go for a night!
Reviewed on Apr 23, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (698 reviews)
"The room was clean and quiet and the bed was comfortable. The breakfast was satisfactory and staff was friendly."
Reviewed on May 20, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Jun 2 to Jun 3
CA $117
CA $150 total
Jun 2 - Jun 3
includes taxes & fees
8.8/10 Excellent! (2,421 reviews)
"We went the property early and got checked in early, the staff was very nice"
Reviewed on May 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 $127 per night from May 27 to May 28
CA $127
CA $184 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (3,488 reviews)
"This location has a lot of potential. Outside it’s beautiful inside and on the premises there’s just no amenities other than the pool. A lot of things were under renovation. Our condo was really out of date all the way around cabinets were falling apart at the hinges weird handles, and cheap fixtures. ..."
Reviewed on May 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.







