Gloucester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.8/10 Exceptional! (352 reviews)
This is a classy place . Great spa beautiful grounds . Colonial Williamsburg is right there . Everything is walkable
We love this place !
Reviewed on Apr 30, 2026
Kingsmill Resort
Kingsmill
Price was CA $2,045, price is now CA $1,587 per person
CA $1,587
per person
Jul 8 - Jul 15
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
Fabulous resort - we stay there every chance we get!
Reviewed on Apr 13, 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 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,003 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
Linden Row Inn
Downtown Richmond
Price was CA $1,619, price is now CA $1,292 per person
CA $1,292
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.2/10 Wonderful! (1,381 reviews)
The property is in a great downtown location near restaurants and other attractions. Very clean, large rooms, lovely furnishings. The restaurant had closed the week before our stay and we weren’t aware, but great local options were very close by. Otherwise our stay was great.
Reviewed on Apr 30, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $129 per night from May 28 to May 29
CA $129
CA $144 total
May 28 - May 29
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 $160 per night from May 21 to May 22
CA $160
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 $107 per night from May 20 to May 21
CA $107
CA $138 total
May 20 - May 21
includes taxes & fees
8.8/10 Excellent! (2,357 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
