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.
Wingate by Wyndham Richmond Short Pump
Short Pump
Price was CA $1,545, price is now CA $1,234 per person
CA $1,234
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.4/10 Very Good! (1,829 reviews)
There was no accommodation for disabled or handicapped visitors the toilet was very not even a toilet helper to help no handicapped rails in bathroom my sister had knee and hip surgery and I requested a handicapped room and breakfast was fair no fruit only green apples I will not be staying at this hotel again Hilton was next door same price I do visit short pump twice a year for shopping was planning a ladies fellowship next year will not be using this hotel
Reviewed on May 6, 2026
Graduate by Hilton Richmond
Downtown Richmond
Price was CA $1,799, price is now CA $1,490 per person
CA $1,490
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.4/10 Very Good! (1,369 reviews)
Great staff, great property, and lovely bars.
Reviewed on May 10, 2026
Hotel Petersburg, Tapestry Collection By Hilton
Price was CA $1,672, price is now CA $1,392 per person
CA $1,392
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
9.2/10 Wonderful! (167 reviews)
We enjoyed two nights in the hotel. The staff is very friendly and helpful. Being located in Old Towne, we were able to walk to shops and some very good restaurants.
Reviewed on May 10, 2026
Hilton Richmond Hotel & Spa/Short Pump
Short Pump
Price was CA $1,907, price is now CA $1,588 per person
CA $1,588
per person
Jun 22 - Jun 28
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
Perfect location
Perfect staff
Excellent staff
Reviewed on May 11, 2026
Gloucester Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
The price is CA $130 per night from May 28 to May 29
CA $130
CA $145 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (693 reviews)
They didn't clean the room every day.
Reviewed on May 8, 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 28 to May 29
CA $162
CA $180 total
May 28 - May 29
includes taxes & fees
9.2/10 Wonderful! (761 reviews)
I stay here several times a year. I enjoy the facility . The gum is perfect the breakfast is perfect and the overall experience is great!
Reviewed on May 10, 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 26 to May 27
CA $108
CA $139 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (2,389 reviews)
Rooms were clean, just old. They do have roaches, they were seen in our suite and in my parents suite. I didn't like having to take out the trash at the end of my stay either. I don't know why that bothers me so much, but having to put garbage in my car, really made my blood boil!! It wasn't bad ...
Reviewed on May 10, 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.
