Gloucester Vacation Packages 2026 from $236

Gloucester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

A house full of steel balls and games

Dumbarton

$236

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game room and barbecue grills. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

avid hotel Richmond North - Ashland by IHG

Save 100% on your flight

$581

per person

Sep 28 - Oct 5

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Candlewood Suites Glen Allen-Short Pump by IHG

$493

per person

Sep 28 - Oct 5

found 22 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Quirk Hotel Richmond

Downtown Richmond

$583

per person

Oct 23 - Oct 25

found 19 hours ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Hyatt Select Richmond/Chester

$534

per person

Oct 11 - Oct 16

found 21 hours ago

Roundtrip flight included

Tampa (TPA) to Richmond (RIC)

This hotel features a 24-hour gym and a seasonal outdoor pool. 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.

Top Gloucester hotels deals

Holiday Inn Express Gloucester by IHG

6639 Forest Hill Ave Gloucester VA

Free Cancellation

$89 nightly

$99 total

Sep 20 - Sep 21

Total with taxes and fees

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

4870 Longhill Road Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$122 total

Sep 9 - Sep 10

Total with taxes and fees

A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial aparthotel. 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

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$105 total

Sep 8 - Sep 9

Total with taxes and fees

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

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

105 Visitors Center Dr Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$132 total

Aug 27 - Aug 28

Total with taxes and fees

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

Wyndham Garden Williamsburg Busch Gardens Area

201 Water Country Pkwy Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

Sep 2 - Sep 3

Total with taxes and fees

Pool

Breakfast included

DoubleTree by Hilton Williamsburg

50 Kingsmill Rd Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Sep 8 - Sep 9

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Free WiFi

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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

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 $236. 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.