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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,781 reviews)
All of the Staff are amazing. Clean room. Hot breakfast.

Reviewed on Jul. 12, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Aug 27 - Sep 2
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
10/10 Exceptional! (9 reviews)
We had a wonderful, relaxing weekend stay at Warner Hall. The hosts Christina and Fred were very welcoming and the house and property is amazing. The house (more like mansion) and rooms are huge and comfortable with lots of space for reading a book, etc. We really enjoyed the morning coffee and tea service brought straight to our rooms. We felt like royalty! There's so much history to the Warners, we had no idea. Definitely highly recommend this place if you're looking for a break from being busy busy.

Reviewed on Jul. 9, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,060 reviews)
This is a rather old property which has been renovated, but is still old looking. It also does not really match what is on the website in my opinion and the opinion of other travelers I talked with.

Reviewed on Jul. 10, 2025

Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,003 reviews)
Our stay was ok. The property was having electrical issues and had a huge generator out back. The hallways and elevator were warm, stuffy, and had a faint musty odor. The room was clean but a stuffy degrees when we arrived. The room did cool down after a few hours but we were hot as it was 95 degrees outside and coming from Kings Dominion.

Reviewed on Jul. 7, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,247 reviews)
The room was very spacious and beautiful. I wish there was an outdoor area to sit and enjoy the beautiful scenery, however, there are outdoor patios within walking distance, which made our stay very enjoyable. Will definitely be back.

Reviewed on Jul. 10, 2025

Ready to book your vacation to Gloucester?

 

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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 $161 per night from Jul 20 to Jul 21
CA $161
CA $180 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (695 reviews)
"Staff were excellent, breakfast was great with variety of items, room was clean and comfortable. The only negative is the floor/carpet in the room had a sticky feeling. It seemed clean so idk if it’s a cleaning product but it’s weird."

Reviewed on Jul. 1, 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 $115 per night from Aug 12 to Aug 13
CA $115
CA $169 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (2,835 reviews)
Beautiful place to stay
"We stayed in a first floor apartment. It was much more spacious than we were expecting. It had everything we needed. Very clean and very comfortable. Parking was very convenient. Beautiful looking communal areas. We had the best two nights staying here!"

Reviewed on Jul. 9, 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
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 13 to Jul 14
CA $122
CA $168 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,425 reviews)
"I always enjoy my stay at the Woodlands!!!!"

Reviewed on Jul. 8, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,190 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

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Frequently asked questions

How much does a Gloucester vacation package cost?
You'll find cheap prices from CA $935 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.