Title: Gloucester Vacation Packages & Trips 2026 from CA $976 | 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 $976 per person Jun 12 - Jun 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Richmond (RIC) 9/10 Wonderful! (1,007 reviews) Breakfast was good. Staff was friendly. My only grip was that I was on the first floor but the curtains did not close. So, the outside lights kept me awake. Reviewed on Mar 7, 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 $1,227 per person May 19 - May 23 found 8 hours ago Roundtrip non-stop flight included Toronto (YTO) 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 $1,107 per person Jun 12 - Jun 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Richmond (RIC) 8.4/10 Very Good! (1,373 reviews) Rooms are decent, nothing to write home about, but location is great! Reviewed on Mar 17, 2026 ![Quirk Hotel Richmond](https://images.trvl-media.com/lodging/12000000/11590000/11581300/11581272/4931a5b8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quirk Hotel Richmond Downtown Richmond CA $1,186 per person Jun 12 - Jun 15 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Richmond (RIC) 8.8/10 Excellent! (1,005 reviews) Nestled in a beautifully restored early 20th-century building on West Broad Street, Quirk Hotel is a love letter to Richmond's creative soul. The rooms are sharp and well-appointed, with an industrial-meets-modern aesthetic and art everywhere that feels genuinely curated rather than decorative. The rooftop bar is a highlight — great skyline views, solid cocktails, and a vibe that makes you want to linger. Demi, the ground-floor restaurant, punches well above hotel-dining expectations, and a busy brunch crowd of locals tells you everything you need to know. The boutique charm does come at boutique prices, and the Broad Street location, while walkable to galleries and restaurants, puts you a bit of a distance from the riverfront and other parts of the city. Parking is worth planning ahead for. But as Richmond hotels go, Quirk earns its reputation as a place that feels genuinely rooted in the city rather than imported from a generic hospitality brand. It's a distinctive, worthwhile stay. Reviewed on Mar 16, 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 $98 CA $128 total Mar 31 - Apr 1 includes taxes & fees 8.8/10 Excellent! (2,165 reviews) Clean and comfy rooms. Not a fan of having to pay a resort fee when I don't use any of those amenities. There really needs to be an option to opt out of amenities so I'm not paying extra for things we're not using. Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%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 $127 CA $183 total Mar 24 - Mar 25 includes taxes & fees 9/10 Wonderful! (3,425 reviews) The property was clean and comfortable Reviewed on Mar 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%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 $109 CA $164 total Mar 24 - Mar 25 includes taxes & fees 8.6/10 Excellent! (1,004 reviews) felt presidential Reviewed on Mar 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%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=19%2F03%2F2026&endDate=20%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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