Book Exclusive Gloucester Vacation Packages

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Gloucester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was CA $1,272, price is now CA $1,072 per person
CA $1,072
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,642, price is now CA $1,334 per person
CA $1,334
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was CA $2,879, price is now CA $2,414 per person
CA $2,414
per person
Oct 3 - Oct 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was CA $2,685, price is now CA $2,253 per person
CA $2,253
per person
Oct 3 - Oct 10
found 20 hours ago
Roundtrip flight included
Moncton (YQM) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Richmond Raceway and Canal Walk are located nearby.
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was CA $1,282, price is now CA $1,105 per person
CA $1,105
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

Top Gloucester hotels deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Free cancellation
The price is CA $127 per night
CA $127
CA $141 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Shoppes at Gloucester and Gloucester Youth Baseball are located nearby.
Pool
Breakfast included
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $117 per night
CA $117
CA $150 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this spa aparthotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Jamestown Settlement are located nearby.
Pool
Hot tub
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $93 per night
CA $93
CA $146 total
Sep 8 - Sep 9
includes taxes & fees
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Jamestown Settlement and Historic Jamestowne are located nearby.
Pool
Parking included
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr Williamsburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $162 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Pool
Breakfast included
Wyndham Garden Williamsburg Busch Gardens Area

Wyndham Garden Williamsburg Busch Gardens Area

3 out of 5
201 Water Country Pkwy Williamsburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $103 per night
CA $103
CA $118 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Pool
Breakfast included
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Free cancellation
Reserve now, pay when you stay
The price is CA $237 per night
CA $237
CA $336 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Pool
Hot tub
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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.

Stay near popular Gloucester attractions

Beaverdam Park

Explore the great outdoors at Beaverdam Park, a lovely green space in Gloucester. Experience the festivals and art scene in this family-friendly area.
See properties

Gloucester Vacations

You've booked your flight and packed your bags, but how much do you really know about your next sensational vacation destination? Sit back, relax and let us guide you through Gloucester.

Gloucester is 14 miles (23 kilometers) from Williamsburg and 25 miles (40 kilometers) from Poquoson.

With so much to do in this area of Chesapeake Bay, it's easy to see why 3,000 people reside here.

Places to visit in Gloucester

After a way to ease the stress of your busy life? Savor the fresh air as you take off on an adventure through York River State Park. After more options? A bit of exercise can do wonders for our mental and physical health. Why not take the family and spend a day in the wide open space at Waller Mill Park? And there's still more going on in the surrounding area. See what life was like many years ago at Rosewell Ruins. Much more than just a stack of old stones, these leftovers of the past offer a fascinating insight into a bygone era.

Where do you fly into for Gloucester?

The buzz and excitement of staying in a new destination never gets old. Once you've arrived at Newport News - Williamsburg International Airport (PHF), the middle of Gloucester will be just 20 miles (32 kilometers) away.

Frequently asked questions

How much are vacation packages to Gloucester?
Travelocity has package deals to Gloucester, including flights and hotels, starting from as low as CA $1,072. With all the extra cash, you could purchase some cool tours or even add on a couple of extra days to your exciting adventure.
How long should my Gloucester vacation be?
There's no hard and fast rule for how long you should spend in Gloucester, but the majority of people decide to stay around 3 nights. Got some flexibility with your travel dates? Consider extending your trip by another night or two. Then you'll have ample time to check out the area's hidden treasures as well.
Where can I get the best vacation package deals for Gloucester?
There are exciting Gloucester package deals to be gained with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep this in mind when you're ready to cross another place off the old bucket list.
Why should I purchase my Gloucester vacation package with Travelocity?
Because you'll never roam alone if you book with us, and we offer round-the-clock customer support and first-rate service to boot. Add to that our Price Match Guarantee and tons of experiences and destinations to choose from. We're here to help you have the vacation of a lifetime.
Can I save on my Gloucester car rental if I combine it with hotels and flights?
With a Gloucester vacation package, you can bundle your hotel, car and flight bookings and save loads. If you can't wait to discover the best of this awesome region, why not check out White House? This popular sight is 177 kilometers from Gloucester. With your own rental car, you'll be there belong long.
Which airport is best for Gloucester?
Richmond Intl. Airport (RIC) is 72 kilometers from the city center and is the beginning point for many adventures. Alternatively, Norfolk Intl. Airport (ORF) is 64 kilometers away from central Gloucester and Newport News - Williamsburg Intl. Airport (PHF) is 31 kilometers away from central Gloucester.
What is there to do in Gloucester?
While veering off the tourist trail can be rewarding, you shouldn't miss the big-name attractions that make a destination famous. Middle Peninsula State Park and Rosewell Ruins are a couple of them in Gloucester.
Where should I stay when visiting Gloucester?
The Holiday Inn Express Gloucester, an IHG Hotel is the top choice of many visitors. Book soon before it's too late.

Photos of local treasures

Browse Gloucester vacation photos for more inspiration

A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.
A steel bridge spanning a river with a control tower, surrounded by calm water and a clear sky.
A steel bridge over calm water with a sunset sky.
A sunset over a calm river with a bridge and distant shoreline.