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.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Price was CA $1,837, price is now CA $1,410 per person
CA $1,410
per person
Jun 25 - Jul 2
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,001 reviews)
Everything was very nice
Reviewed on May 22, 2026
Club Wyndham Kingsgate
Price was CA $1,941, price is now CA $1,535 per person
CA $1,535
per person
Jun 25 - Jul 2
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
Bed was comfy with lots of pillows. We stayed in a “standard one bedroom” cottage-like reservation, while other part of family stayed in a two bedroom. There was a huge difference in accommodations —- theirs was so much nicer and also had a balcony.
Pretty setting convenient by car to William & Mary and historic Williamsburg.
Staff was NOT overbearing in pushing us to commit to an appointment to hear sales pitch. Personnel were courteous and helpful. We did not use amenities; there for graduation.
Reviewed on May 18, 2026
Kingsmill Resort
Kingsmill
Price was CA $1,612, price is now CA $1,336 per person
CA $1,336
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,008 reviews)
What a lovely place! The property is gorgeous, rooms were clean. My toddler had the time of her life at the river pool and collecting shells at the beach. The fitness center was nice. Staff were exceptionally helpful! The only thing I didn't love were the food options - fine for a night but next time we will bring food or explore Williamsburg for better veggies, proteins and healthy options. Overall we had so much fun we booked our next stay before we left!
Reviewed on May 22, 2026
Kings Creek Plantation by TripForth
Price was CA $2,049, price is now CA $1,754 per person
CA $1,754
per person
Jul 25 - Jul 31
just found
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (42 reviews)
This was probably the best property that I've stayed at, maybe ever. I had a family of 8 and the two apartments that we shared were perfect. I will be staying here again
Reviewed on Jul 13, 2025
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $144 per night from May 31 to Jun 1
CA $144
CA $160 total
May 31 - Jun 1
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 $118 per night from Jun 7 to Jun 8
CA $118
CA $150 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (2,419 reviews)
"Room was so clean and spacious. And so much to do around the area. Will definitely be back."
Reviewed on May 22, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from May 26 to May 27
CA $128
CA $185 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (3,459 reviews)
"Great value for the money. It was cold and rainy all weekend, but we could find plenty for our kids to do indoors on the property: game rooms, arts & crafts, indoor pool, and scheduled activities. It’s a big property, but not a far distance from suites to activities (there was also basketball, volleyball, ..."
Reviewed on May 23, 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.
