Title: Gloucester Vacation Packages & Trips 2026 from CA $698 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?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. ![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Vacation Club The Historic Powhatan Williamsburg CA $698 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 9/10 Wonderful! (3,188 reviews) One of the soap dispensers was off the wall in the bathtub. Not something the staff should have missed. Reviewed on Dec 15, 2025 ![Patriots Inn](https://images.trvl-media.com/lodging/22000000/21100000/21095900/21095830/1a70f003_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Patriots Inn CA $791 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 9.4/10 Exceptional! (1,007 reviews) Room was very clean. Staff was welcoming. Reviewed on Dec 10, 2025 ![Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel](https://images.trvl-media.com/lodging/1000000/810000/806400/806310/165fc5e4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel Colonial Williamsburg CA $1,328 per person Feb 28 - Mar 7 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (1,608 reviews) Our room was lovely, clean and so convenient with a nice continental breakfast. Check in staff so helpful and friendly. Just a total great experience. Reviewed on Dec 16, 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 $1,246 per person Feb 28 - Mar 7 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 9.4/10 Exceptional! (1,002 reviews) Wonder experience! The staff were friendly and made the experience amazing; you can tell they love their work. A beautiful hotel in a great vineyard setting. The winery and tasting room and the onsite tavern (restaurant) were exceptional-be sure to make advance reservations, Reviewed on Dec 12, 2025 ![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 $893 per person Jan 20 - Jan 27 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 9.4/10 Exceptional! (310 reviews) Room was somewhat clean. Bathrooms were a little dirty. Good amenities. Reviewed on Nov 23, 2025 ## Ready to book your vacation to Gloucester? Choose your dates ## Gloucester Hotel Deals ![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 $131 CA $146 total Jan 4 - Jan 5, 2026 includes taxes & fees 9/10 Wonderful! (731 reviews) The hotel was clean and nicely decorated. Staff was attentive and courteous. Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=1916863&PinnedHotelID=1916863&HadPinnedHotel=true®ionId=55727) ![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Vacation Club The Historic Powhatan Williamsburg 3601 Ironbound Rd Williamsburg VA CA $92 CA $145 total Jan 2 - Jan 3, 2026 includes taxes & fees 9/10 Wonderful! (3,238 reviews) I did not eat breakfast there. Reviewed on Dec 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F01%2F2026&endDate=03%2F01%2F2026&selected=864071&PinnedHotelID=864071&HadPinnedHotel=true®ionId=55727) ![Vacation Village At Williamsburg](https://images.trvl-media.com/lodging/1000000/1000000/994900/994848/cfc6b534_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village At Williamsburg 4870 Longhill Road Williamsburg VA CA $115 CA $147 total Jan 12 - Jan 13, 2026 includes taxes & fees 8.6/10 Excellent! (1,989 reviews) The carpet was fresh & looked liked it had been recently shampooed. The beds were very comfortable especially with the quality linens. My only concern was with the handicap Accessible shower. It was fine for a wheelchair, but for an individual with mobility problems, it needed to have some type nonslip ... Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=994848&PinnedHotelID=994848&HadPinnedHotel=true®ionId=55727) [See all 2,043 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®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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