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Gloucester flight + hotel vacation packages

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Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the express check-out and WiFi in public areas. You'll also find 6 outdoor tennis courts and an indoor pool.
Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This aparthotel includes free WiFi in public areas and a virtual front desk.

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
Get rates
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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
Get rates
A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
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
Get rates
Free water park access and an outdoor pool are featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
1324 Richmond Road, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.
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
Get rates
This smoke-free resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a free kid's club and mini golf, and supervised childcare is an added bonus. Enjoy the indoor pool and perks like free self parking and free WiFi.
Pool
Parking included
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
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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.

Popular places to visit

Rosewell Ruins

Learn about the local history of Gloucester when you spend time at Rosewell Ruins. Amble around this family-friendly area's picturesque gardens or attend a sporting event.

Rosewell Ruins

Middle Peninsula State Park

You can take time to visit Middle Peninsula State Park during your travels to Gloucester. Experience the festivals and art scene in this family-friendly area.

Middle Peninsula State Park

Riverside Walter Reed Hospital

Though Riverside Walter Reed Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Gloucester while you are here.

Riverside Walter Reed Hospital

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 $308. 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 110 mi from Gloucester. With your own rental car, you’ll be there belong long.
Which airport is best for Gloucester?
Richmond Intl. Airport (RIC) is 45 mi from the city center and is the beginning point for many adventures. Alternatively, Norfolk Intl. Airport (ORF) is 40 mi away from central Gloucester and Newport News - Williamsburg Intl. Airport (PHF) is 19 mi 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