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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.
  • Property entrance
    Sept 9 - Sept 15

    The Commonwealth + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,377 reviews)
    "It has been 35 years since we last visited this property. My wife and I were excited to be able to visit it again and see all the wonderful upgrades!"
    Reviewed July 27, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,543
    CA $1,126
    per traveller
    found 1 day ago
    The Commonwealth
  • Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
    Aug 30 - Sept 4

    Kingsmill Resort + Flight

    Kingsmill
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,012 reviews)
    "The grounds are so beautiful and lush. Great amenities and many are free with their stay such as kayaks, paddle boards, driving range and pools. Room is comfortable especially in the bed! Nice lazy river pool and slide for the kids. Good dinner by the harbor and at the golf course. Highly recommend this stay, we will be back!"
    Reviewed July 27, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - PHF • 1 stop PHF - YYZ • 1 stop
    CA $1,683
    CA $1,299
    per traveller
    found 1 day ago
    Kingsmill Resort
  • Lobby
    Sept 9 - Sept 15

    Omni Richmond Hotel + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,499 reviews)
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,461
    CA $1,159
    per traveller
    found 1 day ago
    Omni Richmond Hotel
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sept 9 - Sept 15

    The Berkeley Richmond, Outset Collection by Hilton + Flight

    Downtown Richmond
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,383 reviews)
    "Our newly renovated room was fantastic and we enjoyed the balcony! I also really liked having a bath robe and luxurious shower products. The location near the canal walk was also nice for my dogs. Staff were friendly!"
    Reviewed July 26, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,587
    CA $1,307
    per traveller
    found 1 day ago
    The Berkeley Richmond, Outset Collection by Hilton
  • Exterior
    Aug 30 - Sept 4

    Kings Creek Plantation by TripForth + Flight

    Williamsburg
    5 nights
    3.5 star property
    8.6/10 - Excellent (43 reviews)
    "This is my second year here and I love it. It's perfectly clean, smells nice and feels homeh. I have a large family and there's always room for my kids to spread out and have their own space. I'll be back again."
    Reviewed July 13, 2026
    Roundtrip • Toronto (YTO) - Richmond (RIC)
    YYZ - PHF • 1 stop PHF - YYZ • 1 stop
    CA $1,896
    CA $1,647
    per traveller
    found 1 day ago
    Kings Creek Plantation by TripForth

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

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG
3.5 star property
1.7 km from Gloucester
7.2 out of 10, Good, (720 reviews)
"The desk staff was amazing and very helpful. Room was, meh. Everything felt damp.. floor, sheets, pillows. Everything. We did not use the pool or gym but did have breakfast. It was what you expect with a continental breakfast. Disappointed that the pancake machine was out of order but these things happen."
The price is CA $128
CA $142 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Gloucester by IHG
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 $1,126 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.