Title: Gloucester Vacation Packages & Trips 2026 from CA $1,058 | 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. ![Graduate by Hilton Richmond](https://images.trvl-media.com/lodging/18000000/17730000/17726000/17725982/36d01625_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton Richmond Downtown Richmond CA $1,058 per person May 31 - Jun 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Richmond (RIC) 8.4/10 Very Good! (1,373 reviews) This property looked and felt tired. Kind of like a hotel that wants to be a luxury hotel ... but hasn't figured it out or shared that with their employees. The bathroom was dirty with scuff marks on the door and shower and literal dirt in the corners. Peeling wallpaper. The bed's top sheet had a foot-long tear right at the top. That was fun. Housekeeping was hit or miss. We finally had to ask for our room to be serviced. And they were the stingiest hotel I've ever seen for leaving towels and washcloths. One per guest, which is problematic if you spend the day sweaty outdoors and want to refresh before dinner. (I will not re-use a washcloth.) Plus, there was very little place to put your clothes. My wife and I were there for a week and there weren't enough hangers for even her clothes. I had to spread my shirts out of the couch. Plus, there was no bureau or chest of drawers to put your other clothes in so we had stuff in our suitcases all week. There was a neat electric tea pot in the room ... but not once during the week did they leave any cups. They have a rec area with a pool table but ... and this is kind of indicative of the rest of the property ... the table felt was coming loose and the three cues were useless: two didn't have tips and the remaining cue was split in the shaft. Do you need a pool table at a hotel? No. Not at all. But if they do offer one, it should at least be in decent shape. Bottom line: There are definitely cleaner, more modern hotel in RVA. Reviewed on Mar 29, 2026 ![Griffin Hotel, an official Colonial Williamsburg Hotel](https://images.trvl-media.com/lodging/14000000/13500000/13499000/13498945/f871738b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Griffin Hotel, an official Colonial Williamsburg Hotel Colonial Williamsburg CA $1,326 per person Apr 30 - May 5 found 6 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (791 reviews) Breakfast was freshly made. Reviewed on Mar 27, 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 $1,331 per person Apr 30 - May 5 found 6 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (1,007 reviews) The whole resort is clean and very attractive. Reviewed on Mar 29, 2026 ![The Commonwealth](https://images.trvl-media.com/lodging/1000000/40000/39900/39891/e7d64633_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Commonwealth Downtown Richmond CA $1,196 per person May 31 - Jun 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Richmond (RIC) 8.8/10 Excellent! (1,387 reviews) Our room was gorgeous! It was quiet and we needed that. The staff was friendly. We ate dinner at the restaurant and received excellent service. We will definitely be back again! Reviewed on Mar 29, 2026 ![The Berkeley Hotel](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/c31357d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Berkeley Hotel Downtown Richmond CA $1,059 per person May 31 - Jun 4 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Richmond (RIC) 8.8/10 Excellent! (1,504 reviews) Amazing location. Very cute and comfortable rooms. Reviewed on Mar 30, 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 $121 CA $154 total Apr 13 - Apr 14 includes taxes & fees 8.8/10 Excellent! (2,207 reviews) Only stayed for one night before heading out on a cruise. Quick check in. Great sized condo. Great price. I run in the mornings and there was plenty of places for me to do that here. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%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 $141 CA $199 total Apr 12 - Apr 13 includes taxes & fees 9/10 Wonderful! (3,438 reviews) This was perfect for my friends bday Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%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 $111 CA $166 total Apr 13 - Apr 14 includes taxes & fees 8.6/10 Excellent! (1,005 reviews) Everything was great Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=863025&PinnedHotelID=863025&HadPinnedHotel=true®ionId=55727) [See all 1,924 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=31%2F03%2F2026&endDate=01%2F04%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.