
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.


Warner Hall
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
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
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
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
Gloucester Hotel Deals

Hampton Inn Gloucester
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

Hilton Vacation Club The Historic Powhatan Williamsburg
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

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.