Title: Gloucester Vacation Packages & Trips 2026 from CA $1,166 | 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/5000000/4170000/4161600/4161536/5bdfdfb0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort CA $1,166 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 9.4/10 Exceptional! (328 reviews) Spacious, clean, except under the night tables beside the bed. Reviewed on Jan 13, 2026 ![Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort](https://images.trvl-media.com/lodging/1000000/10000/5200/5105/8984405d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort CA $1,198 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 8.8/10 Excellent! (439 reviews) We didn't walk much, but the location was excellent Reviewed on Mar 20, 2026 ![Kingsmill Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25624/43d63249_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kingsmill Resort Kingsmill CA $1,435 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 8.8/10 Excellent! (1,007 reviews) The view of the river was awesome. Everything was walking distance. From morning coffee at The Mill to the golf course to the marina at night for dinner. All amenities were very convenient. Reviewed on Mar 16, 2026 ![Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel](https://images.trvl-media.com/lodging/1000000/810000/806400/806310/e9f57606_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel Colonial Williamsburg CA $1,186 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Edmonton (YEG) to Richmond (RIC) 8.8/10 Excellent! (1,695 reviews) Convenience of shuttle Reviewed on Feb 10, 2026 ## Ready to book your vacation to Gloucester? Choose your dates ## Gloucester Hotel Deals ![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 $116 CA $148 total Mar 23 - Mar 24 includes taxes & fees 8.8/10 Excellent! (2,169 reviews) Don’t get a hot tub room without bringing your own cleaning supplies and hot water Reviewed on Mar 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=994848&PinnedHotelID=994848&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 $127 CA $184 total Mar 30 - Mar 31 includes taxes & fees 9/10 Wonderful! (3,413 reviews) Unit was spacious and clean and property was lovely. Reviewed on Mar 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=864071&PinnedHotelID=864071&HadPinnedHotel=true®ionId=55727) ![Hilton Vacation Club Greensprings Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/863100/863025/66d83b6e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Vacation Club Greensprings Williamsburg 3500 Ludwell Pkwy Williamsburg VA Fully refundableReserve now, pay when you stay CA $110 CA $164 total Mar 29 - Mar 30 includes taxes & fees 8.6/10 Excellent! (1,001 reviews) Very pleasant stay. They were very accommodating to our requests. The room was updated and in a great location. Sales pressure was not bad at all and it is a very lovely resort. Will stay again when weather gets warmer. Reviewed on Mar 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=863025&PinnedHotelID=863025&HadPinnedHotel=true®ionId=55727) [See all 1,915 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F03%2F2026&endDate=24%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