Gloucester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Kingsmill Resort
Kingsmill
Price was CA $2,068, price is now CA $1,682 per person
CA $1,682
per person
Jul 31 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
This is top of the line, first-class resort. My jaw dropped and I fell in love. What a great campus, facilities, and rooms.
Reviewed on Jun 28, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,334, price is now CA $1,089 per person
CA $1,089
per person
Jul 31 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
Loved the location. Bearing able to walk to everything. Staff was friendly and helpful. The rooms were very clean. The breakfast wasn’t much and the staff in there wasn’t as good as the rest of the hotel. The hotel overall just needs some updates and upkeep. Starting to look run down, but so was the visitor center.
Reviewed on Jun 27, 2026
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort
Price was CA $1,241, price is now CA $1,112 per person
CA $1,112
per person
Aug 10 - Aug 14
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (454 reviews)
Absolutely pleasantly surprised by how great the property, room, and staff was. Front desk was incredibly helpful, our room was very spacious and comfortable. Outdoor area was great for relaxing and comfortable.
Location couldn’t have been better. 1 mile to both downtown Williamsburg and to the nearest grocery store.
Would recommend to families, our 10 + 7YO were very impressed
Reviewed on Jun 22, 2026
Days Inn & Suites by Wyndham Williamsburg Colonial
Price was CA $1,021, price is now CA $915 per person
CA $915
per person
Aug 20 - Aug 27
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6.2/10 (1,010 reviews)
Avoid room 151 it looks like a crime scene that they didn't bother cleaning up .If your looking for a peaceful place to sleep forget about it people out here blasting there music in the middle of the night.
Reviewed on Jun 26, 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 12 to Jul 13
CA $148
CA $164 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"
Reviewed on Jun 20, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jul 13 to Jul 14
CA $180
CA $220 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (2,544 reviews)
"Friendly staff great space"
Reviewed on Jun 29, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 13 to Jul 14
CA $132
CA $190 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (3,529 reviews)
"It’s perfect for families, has everything you need to do in one place."
Reviewed on Jun 29, 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.
Stay near popular Gloucester attractions
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
