Title: Gloucester Vacation Packages & Trips 2026 from CA $909 | 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. ![Country Inn & Suites by Radisson, Ashland - Hanover, VA](https://images.trvl-media.com/lodging/5000000/4410000/4408100/4408034/1e31c26e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Country Inn & Suites by Radisson, Ashland - Hanover, VA CA $909 per person Jun 10 - Jun 14 found 20 hours ago Roundtrip flight included Winnipeg (YWG) to Richmond (RIC) 9/10 Wonderful! (1,007 reviews) Room was super clean, the check-in co-worker was very efficient and kind, and the area and hotel in general were quiet and comfortable. Was a nice surprise to have a free hot breakfast included. We would absolutely stay here again! Reviewed on Mar 23, 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 $1,801 per person Apr 26 - May 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (791 reviews) I can’t say enough good things about this hotel. Our room was clean, large, beds comfortable, bathroom and two sink areas were convenient. The deck was overlooking a pond and a nice place to relax after walking the restoration area. Being close to the hotel and restaurants was perfect. And, the staff were exceptional. Reviewed on Mar 8, 2026 ![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 $1,046 per person Jun 10 - Jun 14 found 20 hours ago Roundtrip flight included Winnipeg (YWG) to Richmond (RIC) 8.4/10 Very Good! (1,373 reviews) This place is how a hotel should be. It was absolutely fabulous from beginning to end. Staff is wonderful. Hotel is gorgeous. Rooms are clean, updated and nice. Reviewed on Mar 25, 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 $1,838 per person Apr 26 - May 3 found 9 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Richmond (RIC) 8.8/10 Excellent! (1,007 reviews) Beautiful property, nice rooms Reviewed on Mar 25, 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 $932 per person Jun 10 - Jun 14 found 20 hours ago Roundtrip flight included Winnipeg (YWG) to Richmond (RIC) 8.8/10 Excellent! (1,504 reviews) From the moment we entered the Berkeley, the staff was friendly. The service was great! The room was clean and lovely. We had a great stay! We will definitely be returning. Reviewed on Mar 22, 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 $117 CA $150 total Mar 30 - Mar 31 includes taxes & fees 8.8/10 Excellent! (2,194 reviews) This experience fell far below the standard that was advertised and expected. First, I scheduled a timeshare presentation and paid the required $49 fee. After confirming my slot, your team canceled it, stating the time was no longer available, yet my payment has not been refunded. This is unacceptable, ... Reviewed on Mar 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%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 $128 CA $185 total Apr 5 - Apr 6 includes taxes & fees 9/10 Wonderful! (3,433 reviews) Clean room. shower in one bathroom had too much pressure, everything else fine. Reviewed on Mar 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%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 5 - Apr 6 includes taxes & fees 8.6/10 Excellent! (1,014 reviews) Rooms are clean,staff is great and the amenities offered are amazing! Reviewed on Mar 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=863025&PinnedHotelID=863025&HadPinnedHotel=true®ionId=55727) [See all 1,913 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%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. 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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