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A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

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

Top Gloucester vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sept 18 - Sept 20

    Whispering Pines by Hotel O Whitestone VA + Flight

    White Stone
    2 nights
    2.5 star property
    6.2/10 - (158 reviews)
    "Dusty walls; many, many marks and stains on floor, walls, and woodwork. Parking in front of rooms full of cigarette butts and small trash. Price was cheap but definitely not worth the bargain. Needs extensive deep cleaning and repainting."
    Reviewed June 6, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $835
    CA $785
    per traveller
    found 1 day ago
    Whispering Pines by Hotel O Whitestone VA
  • Exterior
    Sept 18 - Sept 20

    Warner Hall + Flight

    Gloucester
    2 nights
    3.0 star property
    10/10 - Exceptional (34 reviews)
    "From the immaculate grounds, to the unreal US history from the Warner family, this destination is a true gem. Phil and Laura; the inn keepers hosted our amazing stay and provided information on the rich history of the site. Austin’s is a wonderful high quality dining establishment on premises with outstanding cuisine, quiet atmosphere, and wonderful wine recommendations by Christian; a top-notch waiter and sommelier. The original house was remodeled to provide outstanding comfort and..."
    Reviewed July 7, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,173
    CA $1,153
    per traveller
    found 1 day ago
    Warner Hall
  • Exterior
    Sept 18 - Sept 20

    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort + Flight

    Williamsburg
    2 nights
    3.5 star property
    9.4/10 - Exceptional (370 reviews)
    "AC was perfect. Fees are ridiculous high price. The wait for your room was a little longer than expected. "
    Reviewed June 29, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $958
    CA $952
    per traveller
    found 1 day ago
    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Discover the most popular places to visit in Gloucester

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.

Gloucester Hotel Deals

Exterior

Warner Hall

Warner Hall
3.0 star property
8.9 km from Gloucester
10.0 out of 10, Exceptional, (34 reviews)
"From the immaculate grounds, to the unreal US history from the Warner family, this destination is a true gem. Phil and Laura; the inn keepers hosted our amazing stay and provided information on the rich history of the site. Austin’s is a wonderful high quality dining establishment on premises with outstanding cuisine, quiet atmosphere, and wonderful wine recommendations by Christian; a top-notch waiter and sommelier. The original house was remodeled to provide outstanding comfort and...
The price is CA $312
CA $347 total
includes taxes & fees
Jul 20 - Jul 21
Warner Hall
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.
See all properties in Gloucester

Frequently Asked Questions

How much does a Gloucester vacation package cost?

You'll find cheap prices from CA $785 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.