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.
Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA

Country Inn & Suites by Radisson, Williamsburg East (Busch Gardens), VA

3 out of 5
Price was CA $961, price is now CA $867 per person
CA $867
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
7.6/10 Good! (178 reviews)
The staff was friendly and helpful, rooms are obviously older, not the cleanest we’ve stayed in. The hallways were hot, but rooms were thankfully cool. The elevator was incredibly slow, constantly beeping. Pool was ok, but water was pretty cloudy. Fine for a couple nights, but not what I expected for the price.

Reviewed on Jul 6, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,675, price is now CA $1,285 per person
CA $1,285
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
This resort had everything you would need that was kid, friendly pool, food and history, all in one.

Reviewed on Jul 6, 2026

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was CA $1,358, price is now CA $1,108 per person
CA $1,108
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (457 reviews)
Fantastic stay for my family! Very comfortable.

Reviewed on Jun 30, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,991, price is now CA $1,673 per person
CA $1,673
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
.

Reviewed on Jul 6, 2026

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,226, price is now CA $1,056 per person
CA $1,056
per person
Aug 23 - Aug 28
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (200 reviews)
⭐⭐⭐⭐⭐ We had a wonderful stay at this resort! The staff was incredibly friendly, welcoming, knowledgeable, and always willing to help with anything we needed. From check-in to check-out, everyone made us feel like valued guests. Our accommodations were clean, spacious, and very comfortable. The property itself was well maintained, with multiple pools and playgrounds that were spotless and provided plenty of options for both relaxation and family fun. The only downsides to our stay were being invited to what was described as a 90-minute presentation that ended up lasting about 2½ hours, and having an issue with our room door on the second day. The battery in the door lock needed to be replaced, which left us locked out of our room for about 45 minutes while it was being fixed. Despite those inconveniences, the overall experience was excellent. The beautiful property, outstanding staff, and great amenities far outweighed the negatives. We would definitely stay here again and recommend this resort to others looking for a relaxing, family friendly and enjoyable vacation.

Reviewed on Jul 3, 2026

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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
Fully refundable
The price is CA $148 per night from Jul 19 to Jul 20
CA $148
CA $164 total
Jul 19 - Jul 20
includes taxes & fees
7.2/10 Good! (712 reviews)
"My room smelled of mold and mildew.. My bedding felt damp. Staff quickly exchanged linens, but next night, those linens felt damp also. Room smelled moldy the entire trip. Other then that it was fair."

Reviewed on Jul 6, 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 $170 per night from Aug 4 to Aug 5
CA $170
CA $210 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (2,582 reviews)
"Whenever my family and I visit the Williamsburg area, Vacation Village is always our first choice. We love how clean and well-maintained the apartments are, and the peaceful, quiet atmosphere makes it easy to relax.One of our favorite features is the swimming pool, along with all the other amenities ..."

Reviewed on Jul 7, 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
The price is CA $132 per night from Jul 20 to Jul 21
CA $132
CA $190 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (3,572 reviews)
"Clean, quiet and beautiful place to relax and a perfect getaway. I would definitely come back."

Reviewed on Jul 6, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
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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 $867 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.