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 $958, price is now CA $818 per person
CA $818
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,790 reviews)
Great location. Very charming property

Reviewed on Jul 4, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,424, price is now CA $1,197 per person
CA $1,197
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
All good and really overall stay.

Reviewed on Jul 2, 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 $1,188, price is now CA $1,032 per person
CA $1,032
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (456 reviews)
Fantastic stay for my family! Very comfortable.

Reviewed on Jun 30, 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 $1,075, price is now CA $965 per person
CA $965
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,240 reviews)
Nice, comfortable

Reviewed on Jul 3, 2026

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,107, price is now CA $997 per person
CA $997
per person
Aug 28 - Sep 1
found 1 day 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

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 $150 per night from Aug 3 to Aug 4
CA $150
CA $187 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (2,560 reviews)
"My family thoroughly enjoyed our stay. So much that we just booked another vacation!"

Reviewed on Jul 4, 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 $132 per night from Jul 19 to Jul 20
CA $132
CA $190 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (3,539 reviews)
"Family friendly!!"

Reviewed on Jul 3, 2026

Hilton Vacation Club The Historic Powhatan 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 $116 per night from Aug 2 to Aug 3
CA $116
CA $166 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,790 reviews)
"Great location. Very charming property"

Reviewed on Jul 4, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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 $818 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.