Book Exclusive Gloucester Vacation Packages

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Gloucester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,119, price is now CA $969 per person
CA $969
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
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.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,449, price is now CA $1,206 per person
CA $1,206
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

3 out of 5
Price was CA $1,260, price is now CA $1,056 per person
CA $1,056
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was CA $1,616, price is now CA $1,376 per person
CA $1,376
per person
Nov 16 - Nov 22
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was CA $1,177, price is now CA $1,014 per person
CA $1,014
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

Top Gloucester hotels deals

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 21 - Sep 22
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.
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 9 - Sep 10
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 $161 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.
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 $236 per night
CA $236
CA $335 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.
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Free cancellation
The price is CA $135 per night
CA $135
CA $157 total
Sep 22 - Sep 23
includes taxes & fees
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Patrick Henry Mall and Newport News Park are located nearby.
Pool
Breakfast included
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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 $969. 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.