Gloucester Vacation Packages 2026 from $604

Gloucester flight + hotel vacation packages

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

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$604

per person

Sep 20 - Sep 25

found 14 hours ago

Roundtrip non-stop flight included

Nashville (BNA) 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.

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

Save 100% on your flight

$984

per person

Sep 12 - Sep 18

found 15 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Richmond (RIC)

A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the express check-out, laundry service, and conference space. You'll also find 6 outdoor tennis courts and an indoor pool.

The Commonwealth

Downtown Richmond

$666

per person

Oct 15 - Oct 20

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.

Wedmore Place

$855

per person

Sep 12 - Sep 18

found 15 hours ago

Roundtrip non-stop flight included

Nashville (BNA) 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.

The Colonies at Williamsburg

$660

per person

Sep 12 - Sep 18

found 15 hours ago

Roundtrip non-stop flight included

Nashville (BNA) 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.

Top Gloucester hotels deals

Holiday Inn Express Gloucester by IHG

6639 Forest Hill Ave Gloucester VA

Free Cancellation

$97 nightly

$108 total

Aug 30 - Aug 31

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

$91 nightly

$104 total

Aug 27 - Aug 28

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

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

$134 total

Aug 3 - Aug 4

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

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$134 total

Aug 10 - Aug 11

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

Wyndham Garden Williamsburg Busch Gardens Area

201 Water Country Pkwy Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

Aug 30 - Aug 31

Total with taxes and fees

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 continental breakfast and free self parking.

Pool

Breakfast included

DoubleTree by Hilton Williamsburg

50 Kingsmill Rd Williamsburg VA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$120 total

Sep 1 - Sep 2

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 $604. 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.