Title: Gloucester Vacation Packages & Trips 2025/2026 from CA $1,247 | 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)

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# Gloucester Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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Save up to CA $1,096 when you book a flight and hotel together\*

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#### 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.

![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 $1,247

per person

Jan 3 - Jan 10

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

8.8/10 Excellent! (744 reviews)

The room was depressing. Some sort of nasty stain on the sofa. Lamps were broken. Room needed painting. Bathroom fixtures needed cleaning. Rug was dirty.

Reviewed on Oct 8, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-03/2026-01-10/?FromAirport=YYZ&Destination=RIC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13498945&paandie=true&dealMarker=OsliZK0xqnJMYzUd7JRMUT5Q2GBQxuL0SNPzJE6cNb8oDbDcl8-y5qMl6AaFK-qV)

![Warner Hall](https://images.trvl-media.com/lodging/113000000/112650000/112645400/112645371/36c9488e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Warner Hall

CA $2,032

per person

Nov 22 - Nov 29

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Richmond (RIC)

10/10 Exceptional! (14 reviews)

We stayed in the main house and the accommodations were excellent and staff very friendly. Seems they are just getting established as the liquor license was issued the day of our departure and in house dining was not yet available. Breakfast was top shelf. It is a bit remote and off property activities require a long drive.

Reviewed on Oct 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RIC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112645371&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365SiQFPz9oMv04yhVE0HL_27sazrlN1wV_aLbyvt7mY_q)

![The Colonies at Williamsburg](https://images.trvl-media.com/lodging/6000000/5090000/5084500/5084488/307a5f35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Colonies at Williamsburg

CA $1,960

per person

Nov 22 - Nov 29

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Richmond (RIC)

9/10 Wonderful! (1,002 reviews)

Vacuum cleaner in condo would be nice

Reviewed on Oct 13, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RIC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5084488&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365U0ap5YifUEBXK9c1dUNCFzBtGWNq3thgNFY-WPchmut)

![Vacation Village At Williamsburg](https://images.trvl-media.com/lodging/1000000/1000000/994900/994848/cfc6b534_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Vacation Village At Williamsburg

CA $1,387

per person

Nov 22 - Nov 29

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Richmond (RIC)

8.8/10 Excellent! (1,732 reviews)

Our 2 bdr condo w/sofa sleeper was great, super spacious, plenty of seating, lrg dining room table seats 6, a very comfortable set up overall!!! No stove/oven but for extended stays n in room cooking there's an electric fry pan, a 2-burner electric cook top, blender, coffee maker w/ 2 coffee packs, toaster, pots n pans, utensils, dishes, glasses, silverware, dish towels/sponge, paper towels, a dishwasher, laundry/dish/washer soap n salt n pepper. There were 2 very large bathrooms, corner jet tub in the master w/a double stand up shower n tub/shower in the other, very generous supply of towels, TP, n starter hair n soap products . Washer n dryer for laundry. Each room had a tv w/ cable n dvd in living room(small dvd selection free at the front desk, nice touch for a rainy day). The online check-in by text/email was very convenient, only took seconds to grab the key cards after a long drive n full day at Busch. The staff was very friendly and accommodating, we requested sofa bedding late at night n it was happily delivered within 10 mins. Specifically, 2 staff members in the rear lobby were very knowledgeable of the area, dining, shopping etc. Plenty of parking per unit, property well maintained, large indoor salt H2O pool n hot tub w/lg seasonal outdoor pools. Play area for littles. Gameroom is terrible. Great location, 5-20mins at most to all attractions, food, shopping etc. Really enjoyed our stay n would recommend n return, very welcoming, hassle free property!!!

Reviewed on Oct 14, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RIC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=994848&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365cWabpDP7rOwlTcfmGQsC5Wqv0uP99msRZi9YZpzTDzc)

![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 $1,516

per person

Nov 22 - Nov 29

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Richmond (RIC)

8.8/10 Excellent! (1,002 reviews)

Beautiful property conveniently located by historical Williamsburg.

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-22/2025-11-29/?FromAirport=YTO&Destination=RIC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=425163&paandie=true&dealMarker=rF3q3WsoxfZMM53Mx3365U0ap5YifUEBXK9c1dUNCFxAudWXnkkwt5SvDCynUQDq)

## Ready to book your vacation to Gloucester?

Choose your dates

## Gloucester Hotel Deals

![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd, Williamsburg, VA

Fully refundableReserve now, pay when you stay

CA $90

CA $143 total

Nov 2 - Nov 3

includes taxes & fees

9/10 Wonderful! (3,118 reviews)

"Such a lovely place to stay. Close to everything, comfortable and relaxing"

Reviewed on Oct 13, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=864071&PinnedHotelID=864071&HadPinnedHotel=true&regionId=55727)

![Vacation Village At Williamsburg](https://images.trvl-media.com/lodging/1000000/1000000/994900/994848/cfc6b534_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Vacation Village At Williamsburg

4870 Longhill Road, Williamsburg, VA

Fully refundableReserve now, pay when you stay

CA $92

CA $122 total

Oct 19 - Oct 20

includes taxes & fees

8.6/10 Excellent! (1,791 reviews)

"Old smell, possibly of smoke, in the unit. You don't notice it so much once inside for a bit. The toilet paper roll holder was broken in the main bathroom."

Reviewed on Oct 11, 2025

[](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=994848&PinnedHotelID=994848&HadPinnedHotel=true&regionId=55727)

![Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel](https://images.trvl-media.com/lodging/1000000/810000/806400/806310/165fc5e4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

105 Visitors Center Dr, Williamsburg, VA

Fully refundableReserve now, pay when you stay

CA $136

CA $185 total

Oct 15 - Oct 16

includes taxes & fees

8.8/10 Excellent! (1,575 reviews)

"The WiFi is so slow."

Reviewed on Oct 12, 2025

[](https://expedia.ca/Hotel-Search?startDate=15%2F10%2F2025&endDate=16%2F10%2F2025&selected=806310&PinnedHotelID=806310&HadPinnedHotel=true&regionId=55727)

[See all 2,250 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025&regionId=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.

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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)

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![QR code to download the app](data:image/png;base64,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)