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.
Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA

2.5 out of 5
Price was CA $904, price is now CA $832 per person
CA $832
per person
Aug 14 - Aug 16
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
6.2/10 (157 reviews)
Room was disapointng compared to price and pictures in add and other discriptions. Furnature was worn lamp shades missing would not stay there again the staff was nice and friendly

Reviewed on Jul 5, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,991, price is now CA $1,673 per person
CA $1,673
per person
Sep 12 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
.

Reviewed on Jul 6, 2026

Country Inn & Suites by Radisson, Petersburg, VA

Country Inn & Suites by Radisson, Petersburg, VA

2.5 out of 5
Price was CA $1,446, price is now CA $1,312 per person
CA $1,312
per person
Sep 12 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
7.8/10 Good! (1,000 reviews)
Had an amazing time and would recommend. Will stay again

Reviewed on Jul 6, 2026

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was CA $1,925, price is now CA $1,756 per person
CA $1,756
per person
Sep 12 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
8.4/10 Very good! (1,396 reviews)
‘no breakfast’ included was a surprise since I bought it through Expedia with breakfast included.

Reviewed on Jul 5, 2026

Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
Price was CA $1,515, price is now CA $1,386 per person
CA $1,386
per person
Sep 12 - Sep 19
found 16 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
9/10 Wonderful! (1,006 reviews)
The greeting from Bill in the evening and Sheila in the morning was wonderful! All the staff were helpful, friendly and did an amazing job of making sure we were comfortable and had everything we needed! The rooms were clean, bathrooms spotless and beds were comfortable. Even the couch in the suite slept well. We were there to spend two days at Kings Dominion and we could not have found a better place to rest after a long day of fun in the heat! I highly recommend this property!!

Reviewed on Jul 5, 2026

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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $148 per night from Jul 19 to Jul 20
CA $148
CA $164 total
Jul 19 - Jul 20
includes taxes & fees
7.2/10 Good! (710 reviews)
"The property has a great all inclusive breakfast and also love the fact that they have an outdoor pool since the neighboring hotel doesn't. I've stayed here in the past when visiting family near by and haven't been disappointed. Also I want to thank the two front desk employees Michelle and Tyrese, ..."

Reviewed on Jul 5, 2026

Holiday Inn Express Gloucester by IHG
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 $170 per night from Aug 5 to Aug 6
CA $170
CA $210 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (2,575 reviews)
"Great for family getaways"

Reviewed on Jul 6, 2026

Vacation Village At Williamsburg
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 $132 per night from Jul 19 to Jul 20
CA $132
CA $190 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (3,561 reviews)
"It was amazing very helpful staff"

Reviewed on Jul 6, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,093 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 $832 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.