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.
Kingsmill Resort
Kingsmill
Price was CA $1,264, price is now CA $1,084 per person
CA $1,084
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
Beautiful resort. The Marina was beautiful and our room was incredible.
Reviewed on May 12, 2026
Hilton Richmond Downtown
Downtown Richmond
Price was CA $1,313, price is now CA $1,107 per person
CA $1,107
per person
Jul 9 - Jul 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,001 reviews)
Not a good breakfast selection for the price of $40 Only breakfast item that was good was the grits.
Reviewed on Apr 18, 2026
Omni Richmond Hotel
Downtown Richmond
Price was CA $1,638, price is now CA $1,400 per person
CA $1,400
per person
Jul 9 - Jul 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,411 reviews)
The staff was attentive, the hotel was up to date and very clean, and there was food within the lobby of the hotel. I was very impressed.
Reviewed on May 15, 2026
Hilton Richmond Hotel & Spa/Short Pump
Short Pump
Price was CA $1,340, price is now CA $1,147 per person
CA $1,147
per person
Jul 9 - Jul 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,007 reviews)
We will never stay again as there was no microwave, paid parking (for an empty parking lot), plus paid parking is not necessary no one is walking to any of the close locations. The paid parking was just a money grab. the bathroom needs up grading. Why is the toilet that close to the shower door and the glass door of shower can’t be opened if the bathroom door is even half open/a glass door at that. The fresh towel rack is over the toilet. Bathroom layout is just weird and small. Plus no free breakfast. We prefer their sister hotel Hampton Inn suite.
Reviewed on May 13, 2026
Quirk Hotel Richmond
Downtown Richmond
Price was CA $1,347, price is now CA $1,167 per person
CA $1,167
per person
Jul 9 - Jul 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,012 reviews)
Had guests stay recently. The food was amazing yet hotel wasn’t busy and stsff
Reviewed on May 14, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (696 reviews)
They didn't clean the room every day.
Reviewed on May 8, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from May 31 to Jun 1
CA $109
CA $140 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (2,392 reviews)
DNU
Reviewed on May 14, 2026
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 29 to May 30
CA $127
CA $184 total
May 29 - May 30
includes taxes & fees
9/10 Wonderful! (3,465 reviews)
The grounds and Williamsburg era residence are lovely. The pools are large and appealing. We thought the dining would be less casual and had to go elsewhere for dinner. We also didn’t want karaoke, just a quiet dinner. Fine for families with kids not for more sophisticated travelers.
Reviewed on May 15, 2026
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.
