
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.

Days Inn & Suites by Wyndham Williamsburg Colonial
Price was CA $1,021, price is now CA $915 per person
CA $915
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6.2/10 (1,010 reviews)
Our Vacation: From Horror Movie to Captain John Smith. After arriving at our first pre-paid hotel only to find it entirely closed for renovations, Expedia successfully passed us around to five different phone agents like a hot potato.They finally booked us a new room. We walked in, and I am convinced it was the set of a budget horror movie. The amenities included:A toilet featuring a literal biological hazard.A bathtub coated in hair and yellow mystery sludge.A fridge coated in unidentifiable spills.Enormous spiderwebs everywhere.Beds sprinkled with "mystery brown flakes."Multiple dead roaches acting as decor.When I called Expedia to complain, an agent named Joanna helpfuly suggested we just switch rooms—because clearly, only that specific room was cursed. Cue my complete mental breakdown in the lobby.Thankfully, the hotel manager was an angel and offered a full refund. I called Expedia back, crying hysterically, and finally reached a saint of a man. He recommended a place that was "outdated but clean."We checked into the Captain John Smith Inn. The front desk guy assured us it wasn’t luxury, but it was spotless. He was right! It looks like 1985 in here, but everything is clean and organized. He even called our room five minutes later to double-check.My husband and I are finally horizontal, relaxing, and breathing clean air!
Reviewed on Jun 30, 2026

Kingsmill Resort
Kingsmill
Price was CA $2,068, price is now CA $1,682 per person
CA $1,682
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
This is top of the line, first-class resort. My jaw dropped and I fell in love. What a great campus, facilities, and rooms.
Reviewed on Jun 28, 2026

The Commonwealth
Downtown Richmond
Price was CA $1,552, price is now CA $1,262 per person
CA $1,262
per person
Aug 2 - Aug 8
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,367 reviews)
Love this hotel!! We stay anytime we’re in Richmond and it’s across from the Capitol building with a beautiful park.
Reviewed on Jun 29, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,334, price is now CA $1,089 per person
CA $1,089
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,782 reviews)
A little outdated but would absolutely go back again. Great value for the price!!
Reviewed on Jun 30, 2026

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort
Price was CA $1,241, price is now CA $1,112 per person
CA $1,112
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (456 reviews)
Fantastic stay for my family! Very comfortable.
Reviewed on Jun 30, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
The price is CA $148 per night from Jul 12 to Jul 13
CA $148
CA $164 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"
Reviewed on Jun 20, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 14 to Jul 15
CA $175
CA $215 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (2,557 reviews)
"Family friendly great place to stay!"
Reviewed on Jun 30, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
The price is CA $132 per night from Jul 14 to Jul 15
CA $132
CA $190 total
Jul 14 - Jul 15
includes taxes & fees
9.2/10 Wonderful! (3,537 reviews)
"⭐⭐⭐⭐⭐ We reserved a one-bedroom unit, but when we arrived, we were pleasantly surprised to learn that no one-bedroom units were available, so we received a complimentary upgrade to a two-bedroom unit. The accommodations were wonderful. Since it was just my husband and me, the location was perfect—quiet ..."
Reviewed on Jun 30, 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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