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.
Griffin Hotel, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $1,514, price is now CA $1,113 per person
CA $1,113
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (820 reviews)
This hotel has absolutely massive rooms by today's standards and shares all amenities with the much more expensive Williamsburg Inn and Williamsburg lodge. The tradeoffs are that you will not have a front desk and the furniture and finishes are much older.
The reality, however, is that the tradeoffs are 100% worth it. The cost is half that of the Lodge and half to 1/4 of the cost of the Inn. You can still use the pool, spa, tennis courts, fitness facilities, concierge, ticket discounts, and everything else that comes with a stay at the fancier neighboring hotels. I would recommend the Griffin. No notes.
Reviewed on May 29, 2026
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
Price was CA $1,283, price is now CA $993 per person
CA $993
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
Loved the suite layout. Very clean with friendly staff. Great place to stay!
Reviewed on Jun 8, 2026
Wedmore Place
Price was CA $1,480, price is now CA $1,167 per person
CA $1,167
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,003 reviews)
Warm was a bit warm, pillows just okay, and we could hear the people in the room above us walking at each step
Reviewed on Jun 10, 2026
Club Wyndham Governor’s Green
Price was CA $1,534, price is now CA $1,211 per person
CA $1,211
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (251 reviews)
Wonderful experience once again. Indoor pool was ice cold due to a broken thermostat. Hopefully it will be fixed when we return.
Reviewed on May 5, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $145 per night from Jun 21 to Jun 22
CA $145
CA $161 total
Jun 21 - Jun 22
includes taxes & fees
7.2/10 Good! (707 reviews)
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."
Reviewed on Jun 9, 2026
Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jul 12 to Jul 13
CA $163
CA $181 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (768 reviews)
"Everything was great. Everyone was polite."
Reviewed on Jun 11, 2026
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Jun 15 to Jun 16
CA $168
CA $207 total
Jun 15 - Jun 16
includes taxes & fees
8.8/10 Excellent! (2,488 reviews)
"It was awesome I will go back 😄"
Reviewed on Jun 11, 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.
