Title: Gloucester Vacation Packages & Trips 2026 from CA $873 | 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

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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.

![Hilton Vacation Club The Historic Powhatan Williamsburg](https://images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Vacation Club The Historic Powhatan Williamsburg

CA $873

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

9/10 Wonderful! (3,188 reviews)

Generally a nice place to stay. Clean rooms and friendly staff.

Reviewed on Dec 24, 2025

![Patriots Inn](https://images.trvl-media.com/lodging/22000000/21100000/21095900/21095830/1a70f003_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Patriots Inn

CA $965

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

9.4/10 Exceptional! (1,007 reviews)

clean room, great amenities

Reviewed on Dec 20, 2025

![Whispering Pines by Hotel O Whitestone VA](https://images.trvl-media.com/lodging/4000000/3910000/3907800/3907766/ecd18e18_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Whispering Pines by Hotel O Whitestone VA

CA $1,064

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

6.2/10 (146 reviews)

Not bad for a mid century motel. Room was small but I would call it european. Bathroom dated but clean. Needed a light bulb in shower, lampshade for table lamp, and smoke detector hooked up. When we checked in we had to air it out because of the sanitation smell but other than that I would stay again.

Reviewed on Oct 13, 2025

![Embassy Suites Williamsburg](https://images.trvl-media.com/lodging/1000000/450000/445900/445849/b64dbd37_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Embassy Suites Williamsburg

CA $1,027

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

8.4/10 Very Good! (1,002 reviews)

The staff at this Embassy Suites was sooo nice! Very friendly and super helpful. The breakfast was delicious.

Reviewed on Dec 24, 2025

![Kingsmill Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25624/3f82f1eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kingsmill Resort

Kingsmill

CA $1,217

per person

Jan 29 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Richmond (RIC)

8.8/10 Excellent! (1,001 reviews)

The spa, indoor pool, and hot tub were great, and the customer service was very good. But the toilet in our unit wasn't functioning properly and we had to call maintenance every day to fix it. That should have been fixed before they had anyone stay in the unit. Also the property was presented as a resort but it's a resort in a gated community with residents as well as guests which gives a different vibe. There were 4 bugs in our unit, it seems they need better pest control.

Reviewed on Dec 11, 2025

## Ready to book your vacation to Gloucester?

Choose your dates

## Gloucester Hotel Deals

![Holiday Inn Express Gloucester by IHG](https://images.trvl-media.com/lodging/1000000/470000/462100/462015/fd1da4fc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Holiday Inn Express Gloucester by IHG

6639 Forest Hill Ave Gloucester VA

Fully refundable

CA $130

CA $145 total

Dec 31 - Jan 1, 2026

includes taxes & fees

7/10 Good! (663 reviews)

The tub wasn't clean but everything else was satisfactory

Reviewed on Dec 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=462015&PinnedHotelID=462015&HadPinnedHotel=true&regionId=55727)

![Hampton Inn Gloucester](https://images.trvl-media.com/lodging/2000000/1920000/1916900/1916863/24cbd909_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn Gloucester

6638 Forest Hill Ave Gloucester VA

Fully refundableReserve now, pay when you stay

CA $134

CA $149 total

Jan 25 - Jan 26, 2026

includes taxes & fees

9/10 Wonderful! (734 reviews)

Room was very spacious and clean. Front desk staff friendly and helpful. Would definitely stay here again.

Reviewed on Dec 16, 2025

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=1916863&PinnedHotelID=1916863&HadPinnedHotel=true&regionId=55727)

![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)

### 

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA

Fully refundableReserve now, pay when you stay

CA $92

CA $144 total

Jan 1 - Jan 2, 2026

includes taxes & fees

9/10 Wonderful! (3,254 reviews)

The suite was great - spacious, clean and with all the amenities. The location is great as well.

Reviewed on Dec 22, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=864071&PinnedHotelID=864071&HadPinnedHotel=true&regionId=55727)

[See all 2,049 properties in Gloucester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F12%2F2025&endDate=27%2F12%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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