
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.

The Commonwealth
Downtown Richmond
Price was CA $1,604, price is now CA $1,198 per person
CA $1,198
per person
Jun 19 - Jun 26
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,360 reviews)
Great location, friendly staff, and spacious rooms. My stay was only marred by the very noisy family next door -- and the fact that I could hear the kids arguing late at night through the shared wall. Not really the Commonwealth's fault but the one reason I gave 4 rather than 5 stars. (I could also hear the elevator dinging outside my door.)
Reviewed on Apr 23, 2026

Graduate by Hilton Richmond
Downtown Richmond
Price was CA $1,635, price is now CA $1,211 per person
CA $1,211
per person
Jun 19 - Jun 26
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Richmond (RIC)
8.4/10 Very Good! (1,357 reviews)
Clean and updated rooms. Bar staff was great and bar is open late
Reviewed on Apr 26, 2026

Holiday Inn Club Vacations Williamsburg Resort by IHG
Price was CA $2,550, price is now CA $2,008 per person
CA $2,008
per person
Jul 19 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (564 reviews)
I would definitely stay at this property again. The rooms were impeccable. We made use of the basketball court and the pool. Plenty of food options just 5 minutes from the hotel. Yes, they will try to sell you a timeshare. But, I made my lack of interest clear as soon as I found out I had to get my key from a salesperson's office and they weren't too pushy after that. Staff was easily accessible for questions via text. 10/10.
Reviewed on Apr 28, 2026

Wedmore Place
Price was CA $1,727, price is now CA $1,362 per person
CA $1,362
per person
Jul 19 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,000 reviews)
We enjoyed our stay at Wedmore Place. We were there for a wedding which was absolutely beautiful. It was nice to stay at the same location as the ceremony and reception. The breakfasts were good with ladies who couldn't do enough for us. We enjoyed our complimentary wine flights and the free bottle of wine. Our only complaint was the noise from the room above which had 2 children running all over the place. We knew as soon as they were awake in the morning. Ask for a room on the 2nd floor. Soundproofing needs to be installed at this hotel.
Reviewed on Apr 27, 2026

Club Wyndham Governor’s Green
Price was CA $1,741, price is now CA $1,382 per person
CA $1,382
per person
Jul 19 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (248 reviews)
I had the 3 bedroom condo and there were three adults staying. Everything just as advertised, except the WiFi was a hit or miss. Even with that I would highly recommend this property and I plan to book another stay this year.
Reviewed on Apr 24, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $153 per night from May 7 to May 8
CA $153
CA $171 total
May 7 - May 8
includes taxes & fees
7.2/10 Good! (689 reviews)
Perfect
Reviewed on Apr 10, 2026

Hampton Inn Gloucester
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 21 to May 22
CA $161
CA $179 total
May 21 - May 22
includes taxes & fees
9.2/10 Wonderful! (755 reviews)
Very polite
Reviewed on Apr 24, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from May 17 to May 18
CA $108
CA $139 total
May 17 - May 18
includes taxes & fees
8.8/10 Excellent! (2,350 reviews)
Love the rooms and the property grounds. Everything is clean however the indoor pool, which was the main reason for staying here was a huge disappointment full of unruly kids, not being watched by their parents. Honestly, I think some of them were sneaking in to use the facilities and not actually ...
Reviewed on Apr 28, 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.







