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.
Candlewood Suites Richmond Airport by IHG

Candlewood Suites Richmond Airport by IHG

2.5 out of 5
Price was CA $971, price is now CA $826 per person
CA $826
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
7.6/10 Good! (1,006 reviews)
Very clean, great rooms. Staff was wonderful.

Reviewed on Jul 11, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,255, price is now CA $973 per person
CA $973
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
Hotel was cute but dated. Despite lots of ads touting their restaurant and bar, it was closed.

Reviewed on Jul 12, 2026

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was CA $1,169, price is now CA $983 per person
CA $983
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,414 reviews)
Close to food and biking and hiking trails

Reviewed on Jul 11, 2026

Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was CA $1,891, price is now CA $1,607 per person
CA $1,607
per person
Sep 13 - Sep 20
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (580 reviews)
This is a time share property and even if you are there having booked a hotel stay paying a full hotel price they will make it time share uncomfortable for you. Having spent a full half hour checking in, a significant amount of that time waiting for their time share staff to be available to give you your hotel keys I had finally had enough and told them how unacceptable this was and for the front desk staff to just give me the key. You'd think I had asked for the nuclear codes, but amidst a loud scoff I was finally given keys. They will also call your room and text you to get you to bite on the time share stuff during your stay. I have stayed at many similar properties previously and without exception if you are booking a hotel room and paying hotel prices they leave you alone for the time share sales hounding. These guys do not understand that and are able to make your hotel stay quite uncomfortable. They need to start realizing the difference between people arriving for a time share pitch, probably staying for close to free, and hotel customers paying the rack rate.

Reviewed on Jul 8, 2026

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Gloucester Hotel Deals

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 $131 per night from Jul 19 to Jul 20
CA $131
CA $189 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (3,606 reviews)
"The Hotel was a wonderful experience. Due to construction, activities were canceled for a couple days. There was a lot tree maintenance going on. So you should good. We do plan to go back. The room was wonderful. The staff polite and courteous. The patio was comfortable. Generous closet and Bathroom ..."

Reviewed on Jul 12, 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 $109 per night from Jul 14 to Jul 15
CA $109
CA $157 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (1,812 reviews)
"Liked the location and the free shuttle to Colonial Williamsburg. The free breakfast was ok but it’s nothing bad to say about it. Liked the decor of the room. The staff are helpful and nice . Had a great stay."

Reviewed on Jul 11, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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 $176 per night from Aug 2 to Aug 3
CA $176
CA $215 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (2,607 reviews)
"Family friendly! Great price!"

Reviewed on Jul 10, 2026

Vacation Village At Williamsburg
See all 2,095 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 $826 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.