Gloucester Vacation Packages

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Flight and hotel packages to Gloucester

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
New York (JFK) 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 spa tub and perks like free self parking and free WiFi.
Bluegreen Vacations Patrick Henry Square, Ascend Resort

Bluegreen Vacations Patrick Henry Square, Ascend Resort

3 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
New York (JFK) to Richmond (RIC)
This hotel features an indoor pool and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.
Wedmore Place

Wedmore Place

3.5 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
New York (JFK) to Richmond (RIC)
This boutique hotel features an attached winery, a full-service spa, and a restaurant. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
New York (JFK) 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.
Patriots Inn

Patriots Inn

2.5 out of 5
per person
Jul 18 - Jul 21
Roundtrip flight included
New York (JFK) to Richmond (RIC)
This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the spa tub and perks like free self parking.

Top Gloucester hotel deals

Holiday Inn Express Gloucester, an IHG Hotel

Holiday Inn Express Gloucester, an IHG Hotel

3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Free Cancellation
The price is $119 per night
$119
per night
May 6 - May 7
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.
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 $116 per night
$116
per night
May 7 - May 8
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 cooked-to-order breakfast and free self parking.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road, Williamsburg, VA
Free Cancellation
The price is $217 per night
$217
per night
May 5 - May 6
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.
Hot Tub
Pool
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 $76 per night
$76
per night
May 9 - May 10
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.
Fort Magruder Historic Williamsburg, Trademark by Wyndham

Fort Magruder Historic Williamsburg, Trademark by Wyndham

3.5 out of 5
6945 Pocahontas Trail, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
The price is $76 per night
$76
per night
May 5 - May 6
This hotel features an indoor pool, a spa tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Best Western Historic Area Inn

Best Western Historic Area Inn

2.5 out of 5
201 Bypass Road, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
The price is $62 per night
$62
per night
May 5 - May 6
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Breakfast included
Pool
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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 in Gloucester

Image for Riverside Walter Reed Hospital

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
Image for Middle Peninsula State Park

Middle Peninsula State Park

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

Middle Peninsula State Park
Image for Gloucester Museum of History

Gloucester Museum of History

4/5(1 review)

You can study the exhibits at Gloucester Museum of History, a museum with a storied past, during your trip to Zanoni. Experience the festivals and art scene in this family-friendly area.

Gloucester Museum of History

Frequently asked questions

How much are vacation packages to Gloucester?
With deals starting as low as $451, flight and hotel packages are the perfect way to stretch your travel budget. Gloucester, here you come!
How long should my Gloucester vacation be?
Most sightseers stay in Gloucester for an average of 2 nights. But traveling is all about exploring new places and creating unforgettable memories — why not lock in a few additional nights so you can do just that?
Where can I get the best vacation package deals for Gloucester?
For an amazing Gloucester package deal, book with Travelocity. Take your pick from as many as 400 airlines and 1,000,000 properties worldwide to create your ultimate escape — it couldn’t be simpler.
Why should I purchase my Gloucester vacation package with Travelocity?
Travel is all about making cherished memories and leaving all your worries behind — which is why we have a team of customer service experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best deal available on our superb range of vacation destinations. So what are you waiting for? There’s no time like the present to secure the vacation of a lifetime.
Can I save on my Gloucester car rental if I book it with hotels and flights?
Certainly — bundle your flight, hotel and car into a Gloucester vacation package and you can save loads. With so many places to explore in and around Gloucester, that rental car will make it easy to explore. Once you’ve settled into the driver’s seat, hit the wide open road and head to White House, an unmissable sight roughly 110 mi from Gloucester.
What is the best time of year to go to Gloucester?
You’ll pick up the cheapest hotel prices in and pay the most during . You can usually expect it to be less busy in November, December and January, while there’ll be more fellow travelers to hang out with in the months of April, May and September. It all depends on what you’re willing to spend, the weather conditions and how well you handle crowds.
Which airport is best for Gloucester?
Norfolk Intl. Airport (ORF) is one of the best airports for Gloucester. You’ll find it 40 mi southeast of the buzzing city center. Your other choices are Richmond Intl. Airport (RIC) (45 mi away from central Gloucester) and Newport News - Williamsburg Intl. Airport (PHF) (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 ignore the popular sights that make a place famous. Gloucester Museum of History and Middle Peninsula State Park are just two of them in Gloucester.
Where should I stay when visiting Gloucester?
Many visitors hit the hay at the Holiday Inn Express Gloucester, an IHG Hotel. It’s sure to be a good base for your Gloucester vacation.