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.
Days Inn & Suites by Wyndham Williamsburg Colonial

Days Inn & Suites by Wyndham Williamsburg Colonial

2.5 out of 5
Price was CA $1,021, price is now CA $915 per person
CA $915
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6.2/10 (1,010 reviews)
Our Vacation: From Horror Movie to Captain John Smith. After arriving at our first pre-paid hotel only to find it entirely closed for renovations, Expedia successfully passed us around to five different phone agents like a hot potato.They finally booked us a new room. We walked in, and I am convinced it was the set of a budget horror movie. The amenities included:A toilet featuring a literal biological hazard.A bathtub coated in hair and yellow mystery sludge.A fridge coated in unidentifiable spills.Enormous spiderwebs everywhere.Beds sprinkled with "mystery brown flakes."Multiple dead roaches acting as decor.When I called Expedia to complain, an agent named Joanna helpfuly suggested we just switch rooms—because clearly, only that specific room was cursed. Cue my complete mental breakdown in the lobby.Thankfully, the hotel manager was an angel and offered a full refund. I called Expedia back, crying hysterically, and finally reached a saint of a man. He recommended a place that was "outdated but clean."We checked into the Captain John Smith Inn. The front desk guy assured us it wasn’t luxury, but it was spotless. He was right! It looks like 1985 in here, but everything is clean and organized. He even called our room five minutes later to double-check.My husband and I are finally horizontal, relaxing, and breathing clean air!

Reviewed on Jun 30, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $2,068, price is now CA $1,682 per person
CA $1,682
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
This is top of the line, first-class resort. My jaw dropped and I fell in love. What a great campus, facilities, and rooms.

Reviewed on Jun 28, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,552, price is now CA $1,262 per person
CA $1,262
per person
Aug 2 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,367 reviews)
Love this hotel!! We stay anytime we’re in Richmond and it’s across from the Capitol building with a beautiful park.

Reviewed on Jun 29, 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 $1,334, price is now CA $1,089 per person
CA $1,089
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
A little outdated but would absolutely go back again. Great value for the price!!

Reviewed on Jun 30, 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 $1,241, price is now CA $1,112 per person
CA $1,112
per person
Aug 10 - Aug 14
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

Ready to book your vacation to Gloucester?

 

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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
The price is CA $148 per night from Jul 12 to Jul 13
CA $148
CA $164 total
Jul 12 - Jul 13
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 $175 per night from Jul 14 to Jul 15
CA $175
CA $215 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (2,557 reviews)
"Family friendly great place to stay!"

Reviewed on Jun 30, 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 14 to Jul 15
CA $132
CA $190 total
Jul 14 - Jul 15
includes taxes & fees
9.2/10 Wonderful! (3,537 reviews)
"⭐⭐⭐⭐⭐ We reserved a one-bedroom unit, but when we arrived, we were pleasantly surprised to learn that no one-bedroom units were available, so we received a complimentary upgrade to a two-bedroom unit. The accommodations were wonderful. Since it was just my husband and me, the location was perfect—quiet ..."

Reviewed on Jun 30, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,098 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

Rosewell Ruins

6.0/10 (2 reviews)
Learn about the local history of Gloucester when you spend time at Rosewell Ruins. Amble around this family-friendly area's picturesque gardens or attend a sporting event.
See properties

Frequently asked questions

How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $915 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.