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.
Williamsburg Inn, an official Colonial Williamsburg Hotel
Colonial Williamsburg
Price was CA $2,879, price is now CA $2,026 per person
CA $2,026
per person
Jul 11 - Jul 18
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.8/10 Exceptional! (352 reviews)
Room exceptionally clean. Nice little touches in room including turndown service. Valets very helpful and professional.
Reviewed on Apr 20, 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 1 day 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
Hilton Richmond Hotel & Spa/Short Pump
Short Pump
Price was CA $1,748, price is now CA $1,359 per person
CA $1,359
per person
Jul 11 - Jul 18
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,006 reviews)
Great customer service. Very clean hotel. The only complaint was the parking… we had to wait about 30 minutes to find a parking spot on Saturday night; other than that, highly recommend.
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 1 day 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
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 10 to May 11
CA $153
CA $171 total
May 10 - May 11
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 $162 per night from May 21 to May 22
CA $162
CA $180 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 20 to May 21
CA $108
CA $139 total
May 20 - May 21
includes taxes & fees
8.8/10 Excellent! (2,355 reviews)
Great Property
Reviewed on Apr 29, 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.
