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, Gloucester Museum of History 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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was CA $707, price is now CA $592 per person
CA $592
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,000 reviews)
Excellent resort. Amenities were great.

Reviewed on Jul 11, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,216, price is now CA $1,001 per person
CA $1,001
per person
Aug 26 - Aug 30
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (828 reviews)
Location, location, location with an amazing view of the pond. Loved interacting with the horses.

Reviewed on Jul 13, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,670, price is now CA $1,397 per person
CA $1,397
per person
Oct 4 - Oct 10
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
Cheap shower heads. Adjoining rooms Room had terrible view Poor restaurant options on property No daily room cleaning

Reviewed on Jul 14, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,214, price is now CA $1,068 per person
CA $1,068
per person
Oct 4 - Oct 10
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,790 reviews)
Everything you need is on site. Close enough to walk to the historical district or they offer shuttle. Visitor center and two gift shops all on hotel property. Our room was amazing.

Reviewed on Jul 15, 2026

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,249, price is now CA $1,101 per person
CA $1,101
per person
Oct 4 - Oct 10
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (200 reviews)
I stayed the weekend here with my family and it was amazing . This place is very close to bush gardens and also water courts there also is a target up the street . I really appreciated how spacious the units are . And also the amenities that come with the stay such as the three different outdoor pool , one indoor pool and also a little mini golf area and I can’t forget about all the daily activities that you can reserve a spot for. I definitely recommend this place .

Reviewed on Jul 13, 2026

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Gloucester Hotel Deals

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jul 29 to Jul 30
CA $133
CA $168 total
Jul 29 - Jul 30
includes taxes & fees
8.8/10 Excellent! (2,617 reviews)
"Everything was great except the bed felt like I was sleeping on a rock."

Reviewed on Jul 14, 2026

Vacation Village At Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 22 to Jul 23
CA $135
CA $186 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,833 reviews)
"Everything you need is on site. Close enough to walk to the historical district or they offer shuttle. Visitor center and two gift shops all on hotel property. Our room was amazing."

Reviewed on Jul 15, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
The price is CA $130 per night from Jul 20 to Jul 21
CA $130
CA $188 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (3,624 reviews)
"It was the perfect location! Close to everything! Property is perfect for families and even for a girls trip"

Reviewed on Jul 15, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,095 properties in Gloucester
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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Stay near popular Gloucester attractions

Beaverdam Park

Explore the great outdoors at Beaverdam Park, a lovely green space in Gloucester. Experience the festivals and art scene in this family-friendly area.
See properties

Frequently asked questions

How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $592 on Expedia for your Gloucester break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Gloucester costs.
What are the cheapest months to go to Gloucester?
You can generally find reduced prices and better availability in January, February and April. Take a look at our cheap Gloucester vacation packages and you could get some excellent off-season deals.
How many days is enough for Gloucester?
The ideal length of your Gloucester vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Gloucester package deals?
Start your search for a Gloucester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Gloucester package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gloucester adventure underway.
Is it cheaper to book a Gloucester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your Gloucester trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Gloucester?
Score amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Gloucester escape.
How to plan a trip to Gloucester?

  1. Pick your travel dates: What you plan to do in Gloucester and your preferred season will help you decide when to get away.
  2. Set your budget: Factor in expenses like flights, meals and transportation when working out how much to set aside for your trip to Gloucester. Then, pick a hotel that matches your budget, whether that's an economical option or a deluxe getaway.
  3. Decide how many days away: Start by making a list of all the attractions you'd like to get to in Gloucester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Gloucester vacation package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.