Title: Gloucester Vacation Packages & Trips 2026 from CA $937 | 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. ![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/e6a3cc9b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Vacation Club The Historic Powhatan Williamsburg CA $937 per person May 9 - May 15 found 1 day ago Roundtrip flight included Calgary (YYC) to Richmond (RIC) 9/10 Wonderful! (3,396 reviews) It was a good stay! Reviewed on Mar 3, 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 $1,572 per person Apr 19 - Apr 23 found 17 hours ago Roundtrip flight included Calgary (YYC) to Richmond (RIC) 8.8/10 Excellent! (765 reviews) Nice location and setting. Reviewed on Mar 2, 2026 ![Club Wyndham Governor’s Green](https://images.trvl-media.com/lodging/2000000/1210000/1203100/1203014/0a67bd1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Club Wyndham Governor’s Green CA $1,170 per person May 9 - May 15 found 1 day ago Roundtrip flight included Calgary (YYC) to Richmond (RIC) 9.2/10 Wonderful! (229 reviews) Love that the rooms are so clean and well maintained. Reviewed on Feb 9, 2026 ![Club Wyndham Kingsgate](https://images.trvl-media.com/lodging/1000000/430000/425200/425163/c1ddc325_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Club Wyndham Kingsgate CA $1,090 per person May 9 - May 15 found 1 day ago Roundtrip flight included Calgary (YYC) to Richmond (RIC) 8.8/10 Excellent! (1,000 reviews) We stayed in a newly remodeled room. With the exception of the painting still in progress, the room/condo and amenities of the resort were amazing. Reviewed on Feb 22, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_55727) ## Ready to book your vacation to Gloucester? Choose your dates ## Gloucester Hotel Deals ![Warner Hall](https://images.trvl-media.com/lodging/113000000/112650000/112645400/112645371/4fc2e938_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Warner Hall 4750 Warner Hall Road Gloucester VA CA $487 CA $542 total Mar 16 - Mar 17 includes taxes & fees 10/10 Exceptional! (25 reviews) Friendly hosts, great rooms, lovely to get tea or coffee in the morning in your room. Breakfast was ok, not the draw. Reviewed on Feb 27, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=112645371&PinnedHotelID=112645371&HadPinnedHotel=true®ionId=55727) ![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/e6a3cc9b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Vacation Club The Historic Powhatan Williamsburg 3601 Ironbound Rd Williamsburg VA Fully refundableReserve now, pay when you stay CA $109 CA $163 total Mar 4 - Mar 5 includes taxes & fees 9/10 Wonderful! (3,408 reviews) Unit clean and bed was comfortable and better than a hotel with full kitchen and living room space. Amenities fee collected on arrival should be waived during winter season when pool and outside activities not possible. Reviewed on Mar 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%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 Fully refundableReserve now, pay when you stay CA $88 CA $116 total Mar 22 - Mar 23 includes taxes & fees 8.8/10 Excellent! (2,125 reviews) Clean room, friendly staff, centrally located Reviewed on Mar 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=994848&PinnedHotelID=994848&HadPinnedHotel=true®ionId=55727) [See all 1,913 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F03%2F2026&endDate=05%2F03%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. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app