Title: Gloucester Vacation Packages & Trips 2026 from CA $1,060 | Expedia.ca [Hotels in Gloucester](https://expedia.ca/Gloucester-Hotels.d55727.Travel-Guide-Hotels)[Vacation Rentals in Gloucester](https://expedia.ca/Gloucester-Vacation-Rentals.d55727.Travel-Guide-VacationRentals)[Flights to Gloucester](https://expedia.ca/Cheap-Flights-To-Gloucester.d55727.Travel-Guide-Flights)[Gloucester Car Rentals](https://expedia.ca/Car-Rentals-In-Gloucester.d55727.Car-Rental-Guide) ![](https://images.trvl-media.com/place/55727/f083fad9-9365-4975-b407-029a614e0e8e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Gloucester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.ca/Middle-Peninsula-State-Park-Gloucester.d637192221073133568.Vacation-Attraction), [Gloucester Museum of History](https://www.expedia.ca/Gloucester-Museum-Of-History-Gloucester.d553248621561864467.Vacation-Attraction) 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. ![Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort](https://images.trvl-media.com/lodging/5000000/4170000/4161600/4161536/5bfda8e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort CA $1,060 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 9.4/10 Exceptional! (310 reviews) Spacious, clean, except under the night tables beside the bed. Reviewed on Jan 13, 2026 ![Griffin Hotel, an official Colonial Williamsburg Hotel](https://images.trvl-media.com/lodging/14000000/13500000/13499000/13498945/56adda1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Griffin Hotel, an official Colonial Williamsburg Hotel Colonial Williamsburg CA $1,275 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (765 reviews) Great hotel, bathroom was was out dated Reviewed on Feb 2, 2026 ![Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort](https://images.trvl-media.com/lodging/1000000/10000/5200/5105/223b911c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort CA $1,159 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (427 reviews) The layout of our room was great for a family vacation. The location is ideal for access to Colonial Williamsburg. My daughter loved the kid friendly amenities like the game room, pool and access to board games through the front desk. Most importantly, though, the staff was so welcoming and helpful. Every person we had contact with from house keeping to the front desk treated us with warmth and kindness. Reviewed on Dec 29, 2025 ![Wedmore Place](https://images.trvl-media.com/lodging/2000000/1630000/1620700/1620663/76dd9569_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wedmore Place CA $1,302 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 9.4/10 Exceptional! (1,002 reviews) Beautiful place inside and out! Reviewed on Feb 3, 2026 ![The Colonies at Williamsburg](https://images.trvl-media.com/lodging/6000000/5090000/5084500/5084488/307a5f35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Colonies at Williamsburg CA $1,121 per person Apr 22 - Apr 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 9/10 Wonderful! (1,000 reviews) I wish we could’ve enjoyed the pool while there. We didn’t pack our swim wear, and when we informed the staff that we would like to go to a local store and purchase swim wear to use their indoor pool facilities, we were informed that being we checked out of our room, we couldn’t come back to the property and use the pool. Felt that being that we had just checked out and were going to come right back and use the pool, im addition, we’ve frequently been to this particular property over the years, they would allow us to use the pool facility for about an hour. That was a little disappointing about the visit. Reviewed on Jan 27, 2026 ## Ready to book your vacation to Gloucester? Choose your dates ## Gloucester Hotel Deals ![Holiday Inn Express Gloucester by IHG](https://images.trvl-media.com/lodging/1000000/470000/462100/462015/fd1da4fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Gloucester by IHG 6639 Forest Hill Ave Gloucester VA Fully refundable CA $124 CA $139 total Feb 11 - Feb 12 includes taxes & fees 7.2/10 Good! (671 reviews) Check in was smooth and courteous. Room was clean and neat. I will stay there next time I'm in the area. Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=462015&PinnedHotelID=462015&HadPinnedHotel=true®ionId=55727) ![Hampton Inn Gloucester](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916863/24cbd909_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Gloucester 6638 Forest Hill Ave Gloucester VA Fully refundableReserve now, pay when you stay CA $133 CA $149 total Feb 22 - Feb 23 includes taxes & fees 9/10 Wonderful! (739 reviews) Room was very spacious and clean. Front desk staff friendly and helpful. Would definitely stay here again. Reviewed on Dec 16, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1916863&PinnedHotelID=1916863&HadPinnedHotel=true®ionId=55727) ![Warner Hall](https://images.trvl-media.com/lodging/113000000/112650000/112645400/112645371/36c9488e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Warner Hall 4750 Warner Hall Road Gloucester VA CA $410 CA $457 total Feb 9 - Feb 10 includes taxes & fees 10/10 Exceptional! (24 reviews) Great room, nice fireplace! Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=112645371&PinnedHotelID=112645371&HadPinnedHotel=true®ionId=55727) [See all 1,907 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=55727) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. 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