Gloucester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Club Wyndham Patriots’ Place

Club Wyndham Patriots’ Place

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,005 reviews)
This property was very well maintained. The staff were very friendly and helpful. I couldn’t find anything to complain about and I highly recommend anyone going to the area to book there.

Reviewed on Aug. 10, 2025

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (219 reviews)
Everything was amazing can't wait to go back 😌

Reviewed on Aug. 15, 2025

Westgate Williamsburg

Westgate Williamsburg

2.5 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
No reviews
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
Kingsgate has lots of amenities and is family oriented

Reviewed on Aug. 16, 2025

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (74 reviews)
It’s very near everything so is convenient,

Reviewed on Aug. 15, 2025

Ready to book your vacation to Gloucester?

 

Choose your dates

Gloucester Hotel Deals

Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Sep 1 to Sep 2
CA $187
CA $208 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (710 reviews)
"Bed comfort and they changed out new towels almost every day"

Reviewed on Aug. 5, 2025

Hampton Inn Gloucester
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 $123 per night from Aug 25 to Aug 26
CA $123
CA $179 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (2,933 reviews)
"Beautiful accommodation, we will be back."

Reviewed on Aug. 16, 2025

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
The price is CA $155 per night from Aug 20 to Aug 21
CA $155
CA $206 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,539 reviews)
"The property was"

Reviewed on Aug. 18, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,231 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

Frequently asked questions

How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $1,063 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.

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