Gloucester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $845, price is now CA $612 per person
CA $612
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
The staff was exceptional, great hospitality! The room had several minor issues, shower door didn’t stay closed, vanity was missing a leg, power bank on one side of the bed didn’t work, a random ballon was on the ceiling(granted we didn’t notice it one of the staff did while trying to get the power bank to work) bar and restaurant was out of multiple items.

Reviewed on Jul 13, 2026

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was CA $863, price is now CA $681 per person
CA $681
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,414 reviews)
For customers interested in historical building

Reviewed on Jul 14, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,216, price is now CA $1,001 per person
CA $1,001
per person
Aug 26 - Aug 30
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (828 reviews)
Location, location, location with an amazing view of the pond. Loved interacting with the horses.

Reviewed on Jul 13, 2026

Quirk Hotel Richmond

Quirk Hotel Richmond

4 out of 5
Downtown Richmond
Price was CA $990, price is now CA $816 per person
CA $816
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,007 reviews)
I’m disabled and staff helped me with their wheelchair

Reviewed on Jul 14, 2026

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was CA $766, price is now CA $631 per person
CA $631
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Richmond (RIC)
8.4/10 Very good! (1,402 reviews)
Room, location and check in were good. I stayed over the 4th of July weekend and one reason I booked was for the rooftop bar to see the fireworks displays. The whole 3 nights myself and others tried to access the rooftop bar but were told it was too hot or elevator was not working all the way up. Also on 4th of July only 1 elevator working out of 3 and it was a busy day.

Reviewed on Jul 14, 2026

Ready to book your vacation to Gloucester?

 

Choose your dates

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 $139 per night from Jul 28 to Jul 29
CA $139
CA $174 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (2,617 reviews)
"Everything was great except the bed felt like I was sleeping on a rock."

Reviewed on Jul 14, 2026

Vacation Village At 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 $138 per night from Jul 22 to Jul 23
CA $138
CA $190 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,832 reviews)
"Everything you need is on site. Close enough to walk to the historical district or they offer shuttle. Visitor center and two gift shops all on hotel property. Our room was amazing."

Reviewed on Jul 15, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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 $130 per night from Jul 22 to Jul 23
CA $130
CA $188 total
Jul 22 - Jul 23
includes taxes & fees
9.2/10 Wonderful! (3,623 reviews)
"We loved our stay! They had a playground right by our unit and it was a great place to run off some steam. We utilized the pools, mini golf and activity center while here. Our unit was clean and staff was super responsive when we needed anything. It was perfect for our family vacation. Close to colonial ..."

Reviewed on Jul 14, 2026

Hilton Vacation Club The Historic Powhatan 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $612 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.