Gloucester Vacations from $383

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Your Gloucester Vacation

There's plenty to love about Gloucester, from its rich history to its coastal scenery and beyond. When you're ready to spend some time in this wonderful city, our Gloucester vacation packages will be just the ticket. Every good trip to Gloucester should include some sightseeing. Where to check out first? Gloucester Museum of History and Middle Peninsula State Park are main attractions. Stop daydreaming and start adventuring. Explore the range of options on Expedia today and finally put your Gloucester vacation plans into action!

The Latest Gloucester Vacation Packages

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
per person
May 28 - Jun 2
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8/10 Very Good! (1,003 reviews)
The staff were personable and very considerate

Reviewed on Apr 18, 2024

Graduate Richmond

Graduate Richmond

4 out of 5
Downtown Richmond
per person
Jul 4 - Jul 7
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.2/10 Very Good! (1,116 reviews)
Best priced hotel in an overpriced market. No bellman.

Reviewed on Apr 17, 2024

Wedmore Place

Wedmore Place

3.5 out of 5
per person
May 28 - Jun 2
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (935 reviews)
Beautiful and special. If you know, you know.

Reviewed on Apr 15, 2024

Wyndham Garden Williamsburg Busch Gardens Area

Wyndham Garden Williamsburg Busch Gardens Area

3 out of 5
per person
May 28 - Jun 2
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
6.8/10 (1,473 reviews)
There was remodeling going on so the property was not very clean.

Reviewed on Apr 14, 2024

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
May 28 - Jun 2
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.6/10 Excellent! (1,001 reviews)
I like that all amenities is included into the price of the room. Things to do for kids and adults. Will recommend with no hesitation.

Reviewed on Apr 16, 2024

Prices and availability subject to change. Additional terms may apply.

Gloucester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Newport News - Williamsburg Intl. Airport (PHF)
Population
3,000
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Gloucester Museum of History, Middle Peninsula State Park and Rosewell Ruins

Gloucester Hotel Deals

Hilton Vacation Club The Historic Powhatan Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is $95 per night from Apr 22 to Apr 23
$95
$136 total
includes taxes & fees
Apr 22 - Apr 23
8.8/10 Excellent! (2,349 reviews)
"The property itself was great. Beautiful grounds and very clean. Front desk staff were very nice as well. I was very disappointed with a couple of things. 1) Was unaware of additional resort fees 2) Eager “time share “ sales people very loud behind you at check in. Had no idea it was timeshare that ..."

Reviewed on Apr 17, 2024

Hilton Vacation Club The Historic Powhatan Williamsburg
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
The price is $107 per night from Apr 24 to Apr 25
$107
$138 total
includes taxes & fees
Apr 24 - Apr 25
8.8/10 Excellent! (1,000 reviews)
Great location and service
"Excellent customer service. Fantastic location for Colonial Williamsburg."

Reviewed on Apr 15, 2024

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Best Western Historic Area Inn
Best Western Historic Area Inn
2.5 out of 5
201 Bypass Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is $62 per night from Apr 22 to Apr 23
$62
$71 total
includes taxes & fees
Apr 22 - Apr 23
7.8/10 Good! (1,076 reviews)
"Good atention"

Reviewed on Apr 15, 2024

Best Western Historic Area Inn
See all 2,047 properties in Gloucester
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.

Explore other types of vacation packages

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All Inclusive Vacations

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Beach Vacations

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Kid Friendly Vacations

Frequently asked questions

How much does a Gloucester vacation package cost?
Chart your own course with our Gloucester vacation packages, which start from just $383. Pick the hotels and flights that match your travel plans. Then, add on a couple of experiences or tours for a one-of-a-kind adventure.
How do I get a cheap travel package to Gloucester?
Bundle your hotels and flights with Expedia to save big on your next exciting adventure. With more than 550 airlines and 1,000,000 hotels globally, your Gloucester vacation package can be customized exactly to suit your budget. With all that extra money, why not throw in one or two awesome experiences and tours? It’s an easy way to unlock even more bargains. Your dream getaway to Gloucester is much closer than you thought!
Where should I stay in Gloucester?
You’ll want to stay where the action is. Many visitors book hotels within easy reach of top attractions, such as Riverside Walter Reed Hospital, Rosewell Ruins and Middle Peninsula State Park.
What are the top hotels in Gloucester?
Book a stay at Enjoy The Simple Life In This Luxury Farmhouse Near Williamsburg. It’s one of the area’s most in-demand properties. Another great option in Gloucester is Right On Main St Shops, Arts, Dining And More.
How far in advance should I book my Gloucester vacation?
While not all airlines advertise tickets early, customers are usually able to start comparing international airfares on Expedia up to 12 months in advance. This is the time you can score some fantastic deals. If you’re booking last minute, you may still be in luck. Discounted prices occasionally appear only weeks prior to departure.
What does an Expedia Gloucester travel package include?
Hotels, flights and rental cars — you’ll find them all here. With Expedia, you can create your Gloucester travel package just the way you want. All you have to do is decide exactly what you need. Once you’ve made your booking, you can add on fun things like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Gloucester travel package?
Locking in all the parts of your getaway together is a terrific way to save. Bundle your car rentals, airfares and hotels into a handy little package. But you’re not limited to hotels. Expedia has all kinds of properties, including vacation rentals such as mountain cabins and short-term homes. The list is almost endless!
Can I choose my airline with a Gloucester Expedia vacation package?
Yes — that’s the beauty of an Expedia vacation package. You can pick and choose your flights, hotels and more. We have access to more than 550 airline partners around the world, so you have loads of choice when creating your Gloucester escape.
If I'm not able to travel, can I cancel my Gloucester vacation package?
Yes, you can. We realize things don’t always go to plan, so we’re here to help if you need to make changes to your Gloucester vacation package. You may be able to cancel or change your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most 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 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
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

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.