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.
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 $1,316, price is now CA $1,034 per person
CA $1,034
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,790 reviews)
The pool was clean and warm. The pool towels were a great size! The ice maker on our wing was broken so we did not have any ice. Front desk staff was nice and helpful.

Reviewed on Jul 2, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,912, price is now CA $1,486 per person
CA $1,486
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
All good and really overall stay.

Reviewed on Jul 2, 2026

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

3 out of 5
Price was CA $1,257, price is now CA $1,064 per person
CA $1,064
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,010 reviews)
The air conditioning in 401 wasn’t great, but Nathalia moved us to 407 and it was perfect. She even gave us a voucher for a free breakfast! She was fantastic and helpful 💛

Reviewed on Jul 2, 2026

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,353, price is now CA $1,176 per person
CA $1,176
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (200 reviews)
I loved all of the activities & many pools to choose to go to. You definitely felt very safe & all of the people who worked there were very courteous and nice! The room was like a 2 bedroom condo, and there was plenty of room for everyone! I will definitely stay here again!

Reviewed on Jul 3, 2026

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

2.5 out of 5
Price was CA $1,312, price is now CA $1,174 per person
CA $1,174
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,240 reviews)
Nice, comfortable

Reviewed on Jul 3, 2026

Ready to book your vacation to Gloucester?

 

Choose your dates

Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
The price is CA $153 per night from Jul 19 to Jul 20
CA $153
CA $171 total
Jul 19 - Jul 20
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"

Reviewed on Jun 20, 2026

Holiday Inn Express Gloucester by IHG
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 $190 per night from Aug 3 to Aug 4
CA $190
CA $232 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,565 reviews)
"It was close to Busch Gardens everywhere else we needed to go on our trip"

Reviewed on Jul 2, 2026

Vacation Village At Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jul 12 to Jul 13
CA $148
CA $209 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (3,536 reviews)
"I did like the room itself however parking and the units being spread out was a little confusing. I feel like the units shouldn't intermingle families with kids with couples that have no kids. I think the two should be separated for a more pleasant experience for both parties."

Reviewed on Jul 3, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,093 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 $1,034 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.