
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.

Days Hotel by Wyndham Williamsburg I-64
Price was CA $832, price is now CA $791 per person
CA $791
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
6.8/10 (110 reviews)
Room is beautiful. Check in was great. Stay has been wonderful.
Reviewed on Nov 16, 2025

Kingsmill Resort
Kingsmill
Price was CA $1,264, price is now CA $1,084 per person
CA $1,084
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
Beautiful resort. The Marina was beautiful and our room was incredible.
Reviewed on May 12, 2026

Whispering Pines by Hotel O Whitestone VA
Price was CA $915, price is now CA $810 per person
CA $810
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
6.2/10 (154 reviews)
Not bad for a mid century motel. Room was small but I would call it european. Bathroom dated but clean. Needed a light bulb in shower, lampshade for table lamp, and smoke detector hooked up. When we checked in we had to air it out because of the sanitation smell but other than that I would stay again.
Reviewed on Oct 13, 2025

Wyndham Garden Williamsburg Busch Gardens Area
Price was CA $954, price is now CA $882 per person
CA $882
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
7/10 Good! (503 reviews)
We were relieved at checked in it was quickly processed and we were acknowledged promptly, Went into our with nice and cleam.
Reviewed on May 10, 2026

Baymont By Wyndham Williamsburg I-64
Price was CA $840, price is now CA $797 per person
CA $797
per person
Jun 19 - Jun 22
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
6.8/10 (53 reviews)
For the price, this was beyond reasonable and exceeded expectations. Parking was convenient and plentiful. You can tell this is a super old hotel but they have done a pretty good job renovating. There were lots of areas that were clearly "landlord specials" to cheapen out, like painting over the entire door and fixtures with the same paint lol.....but despite all of that, it was very clean. Mirror in the bathroom was nice. Fridge was cold. mixed review on the bed....I was comfy but my husband woke up with a sore back. Pillows were great, I wanted to take one home. First morning, there was no hot water and the tub did not drain very well. The bathroom door did not want to shut. Hilariously, there is a sign in the elevator bragging about the WiFi, but the WiFi was actually useless. I had to do work using my hot spot. The TV was supposed to be connected to the WiFi as well, but it wouldnt connect, so we couldnt use Netflix or any of the smart TV features. Overall, it was a good stay. Safe, clean, affordable.
Reviewed on Apr 6, 2026
Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $125 per night from May 28 to May 29
CA $125
CA $139 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (696 reviews)
They didn't clean the room every day.
Reviewed on May 8, 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 31 to Jun 1
CA $108
CA $140 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (2,392 reviews)
DNU
Reviewed on May 14, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from May 26 to May 27
CA $127
CA $183 total
May 26 - May 27
includes taxes & fees
9/10 Wonderful! (3,462 reviews)
Great place for family fun. Spacious room. Lovely property. Good location.
Reviewed on May 15, 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.







