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.
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 $962, price is now CA $866 per person
CA $866
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,006 reviews)
Nice hotel clean quiet all i ask for

Reviewed on Jun 29, 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 1 day 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 $1,039, price is now CA $931 per person
CA $931
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
Staff was very accommodating and helpful Rooms were clean

Reviewed on Jun 30, 2026

Best Western Premier Richmond City Gateway

Best Western Premier Richmond City Gateway

3 out of 5
Price was CA $1,251, price is now CA $1,122 per person
CA $1,122
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8/10 Very good! (1,000 reviews)
The pool area was very clean and tidy, even though we were unable to use it. It was very quiet at night. The facility is at a great location. Very centralized and easy to go downtown . We had a very clean room. We would definitely stay again.

Reviewed on Jun 30, 2026

Four Points by Sheraton Richmond Airport

Four Points by Sheraton Richmond Airport

3.5 out of 5
Montrose
Price was CA $1,355, price is now CA $1,223 per person
CA $1,223
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.2/10 Very good! (1,004 reviews)
Location was great. Plenty of food and grocery stores nearby.

Reviewed on Jul 1, 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 $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 $222 per night from Jul 5 to Jul 6
CA $222
CA $268 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,561 reviews)
"The property and rooms were great. Police and fire activity was daily though. The causes were explained when we asked."

Reviewed on Jul 1, 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 $149 per night from Jul 8 to Jul 9
CA $149
CA $209 total
Jul 8 - Jul 9
includes taxes & fees
9.2/10 Wonderful! (3,547 reviews)
"Clean, but spotty internet. Phones kept shutting down and occasional internet being disconnected."

Reviewed on Jul 1, 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

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 $866 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.