
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.

Best Western PLUS Executive Hotel
Dumbarton
Price was CA $1,238, price is now CA $1,136 per person
CA $1,136
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
7.8/10 Good! (1,005 reviews)
The hotel was extremely dirty. The front lobby’s floors looked as if they’ve not been mopped in months. The furniture was visibly soiled, the carpets in the hallways were caked with dirt, crumbs everywhere, there were pills in front of some of the rooms.
Reviewed on Nov 1, 2026

The Commonwealth
Downtown Richmond
Price was CA $2,316, price is now CA $1,535 per person
CA $1,535
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)
This place has a lot of potential but seems to be under renovation for the past few years. Plus the whole area around it has been under renovation too. The cost of parking was high. The lounge could turn into something cool but isn't much at this time.
Reviewed on Nov 1, 2026

The Berkeley Richmond, Outset Collection by Hilton
Downtown Richmond
Price was CA $1,582, price is now CA $1,387 per person
CA $1,387
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,330 reviews)
A beautiful historical hotel in a good downtown location
The room was very high spec, smelt lovely and was decorated beautifully
Highly recommend 5 stars
Reviewed on Nov 2, 2026

Quirk Hotel Richmond
Downtown Richmond
Price was CA $1,563, price is now CA $1,426 per person
CA $1,426
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,000 reviews)
Beautiful rooftop bar, fun quirky hotel. Would stay again.
Reviewed on Nov 2, 2026

Courtyard by Marriott Richmond Downtown
Downtown Richmond
Price was CA $1,497, price is now CA $1,468 per person
CA $1,468
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,005 reviews)
The location was great, and both rooms were very clean and comfortable. However, there were a few small issues. The person who checked us in was borderline rude, but everyone else was very polite and helpful throughout the weekend. Coffee was available in the lobby at the Starbucks, but was out of cream, cup holders, etc, twice- not a huge issue, but it felt like we were inconveniencing the person working there when we asked for these items. The main issue is that the toilet in one of the two rooms was running non-stop when we checked in and stopped working shortly after that. I reported it to the front desk the next morning and was told that someone would fix it while we were out that day- however, it was still broken when we returned that evening. Since we were a group of friends and the rooms adjoined, we just left the door open and shared the one bathroom both nights. However, this really should have been handled as requested. When we left after the second night, I told the front desk about it again ( so that they could fix it before the next person checked in) and was told that our parking fees would be reimbursed due to the hassle. It's been several weeks now and no one has reached out to do so.
Reviewed on Oct 30, 2026
Gloucester Hotel Deals

Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 9 to Nov 10
CA $135
CA $151 total
Nov 9 - Nov 10
includes taxes & fees

Perfect for long-term workers & short stays—comfort, style & convenience await!
Gloucester VA
8.2/10 Very good! (25 reviews)
"Host was super helpful. Everything we needed was provided.We would stay again."
Reviewed on Oct 10, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Nov 8 to Nov 9
CA $94
CA $147 total
Nov 8 - Nov 9
includes taxes & fees
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.
Stay near popular Gloucester attractions
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







