Gloucester Vacations from $649

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Your Gloucester Vacation

From its coastal scenery to its rich history and beyond, there's loads to like about Gloucester. Discover the wonders of this captivating city with a Gloucester vacation package that's made for you. Eager to do a bit of sightseeing? A trip to Gloucester isn't complete without checking out Middle Peninsula State Park, Gloucester Museum of History and other major attractions. Your Gloucester vacation is clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Gloucester vacation packages

Price found within the past 48 hours. Click for updated prices.
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
Price was $983, price is now $649 per person
$649
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
8.8/10 Excellent! (765 reviews)
Staff always courteous! Lovely stay year after year!

Reviewed on Dec 20, 2025

Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $1,158, price is now $805 per person
$805
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
Beautiful place, wonderful staff and the restaurant is great!

Reviewed on Jan 5, 2026

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $1,159, price is now $816 per person
$816
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9/10 Wonderful! (1,000 reviews)
Amenities, the jetted tub did not work, we ask ahead , bed were uncomfortable

Reviewed on Jan 10, 2026

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $2,824, price is now $2,024 per person
$2,024
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9.8/10 Exceptional! (322 reviews)
Beautiful property, wonderful staff.

Reviewed on Jan 1, 2026

Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,033, price is now $741 per person
$741
per person
Apr 2 - Apr 9
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9/10 Wonderful! (525 reviews)
The property location was excellent for local site seeing and was away from concentrated visitor areas.

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in Gloucester

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

Gloucester Museum of History

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

Gloucester Museum of History

Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
$91 nightly
The price is $101 total per night from Jan 23 to Jan 24
$101 total
Jan 23 - Jan 24
Total with taxes and fees
7.2/10 Good! (668 reviews)
Check in was smooth and courteous. Room was clean and neat. I will stay there next time I'm in the area.

Reviewed on Jan 2, 2026

Holiday Inn Express Gloucester by IHG
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Feb 1 to Feb 2
$109 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (735 reviews)
Room was very spacious and clean. Front desk staff friendly and helpful. Would definitely stay here again.

Reviewed on Dec 16, 2025

Hampton Inn Gloucester
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
$294 nightly
The price is $328 total per night from Jan 14 to Jan 15
$328 total
Jan 14 - Jan 15
Total with taxes and fees
10/10 Exceptional! (24 reviews)
Great room, nice fireplace!

Reviewed on Dec 7, 2025

Warner Hall
See all 2,020 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.

Find the Best Gloucester Vacation Packages

Things to do in and around Gloucester

Gloucester, Virginia, offers a delightful mix of outdoor and family-friendly activities, perfect for a scenic vacation. Enjoy thrilling rides at the amusement park, stroll along the boardwalk, or relax in the recreational areas. For an unforgettable experience, consider exploring vacation packages, romantic getaways, popular tours, and ocean adventures, including memorable sailing trips.

Shopping

For shopping in Gloucester, visit White Marsh Shopping Center, just 5 miles away, offering a mix of family and city vibes. In the heart of Gloucester, check out Walter Reed Plaza and Main Street Center, both providing a diverse shopping experience with a friendly atmosphere.

Recreation

Gloucester Point Beach Park offers a tranquil coastal retreat with sandy shores and scenic views, perfect for relaxation. Kiskiack Golf Club invites you to enjoy a round of golf amidst beautiful landscapes, while Waller Mill Park provides serene walking trails and peaceful green spaces for rejuvenation.

Adventure

Experience thrilling water slides and wave pools at Water Country USA, located 12 miles from Gloucester. Dive into the fun at MagiQuest, an exciting arcade adventure zone, also 12 miles away. For more family fun, bounce around at the Bounce House, situated 13 miles from Gloucester.

Nightlife

In Gloucester, Virginia, enjoy a relaxed nightlife with local pubs and restaurants offering live music and friendly atmospheres. Visit venues like The White Dog Bistro for a casual meal or explore nearby taverns for drinks and conversation, all while soaking in the charm of this historic town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Gloucester

Gloucester, Virginia, is perfect for outdoor family vacations, offering beautiful scenery and a variety of attractions. Explore local points of interest, including Gloucester Beach, the historic Gloucester Cathedral, and the scenic Gloucester Docks and Quays. Whether you're looking to relax on the beach or discover the rich culture of the area, Gloucester has something for everyone to enjoy.

  • Yorktown Beach: Located 12 miles from Gloucester, Yorktown Beach offers a stunning waterfront experience with soft sands and beautiful views of the Chesapeake Bay. It's the perfect spot for relaxation, beach activities, and picnics with family and friends.
  • Rosewell Ruins: Nestled within Gloucester, the Rosewell Ruins are a glimpse into 18th-century architecture and history. This site showcases the remnants of a once-grand mansion, surrounded by lush greenery, making it a serene location for history enthusiasts and photographers alike.
  • Gloucester Museum of History: Situated in the heart of Gloucester, this museum offers a rich exploration of the area's history through engaging exhibits and artifacts. Visitors can learn about local heritage and culture, making it a must-see for those interested in the past.

Tips to save on your trip to Gloucester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Gloucester during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

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Frequently asked questions

How much does a Gloucester vacation package cost?
Offering great value package deals from $649 on Expedia, you'll be pleasantly surprised at how much a vacation to Gloucester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Gloucester?
If you're hoping to snag a cheap Gloucester vacation package, consider visiting in November, December and January. You'll typically find lower prices on accommodations and flights during these months — ideal for travelers wishing to save money.
How many days is enough for Gloucester?
Generally, a handful of days is enough to explore the main sights during your Gloucester vacation. However, if you prefer to have some time to unwind or go on day tours, think about extending your itinerary.
How to find the best Gloucester package deals?
Start your search for a Gloucester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Gloucester package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gloucester escape off to a flying start.
Is it cheaper to book a Gloucester vacation as a package?
You can enjoy significant savings on your Gloucester retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Gloucester?
If you're considering a spontaneous Gloucester vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Gloucester vacation packages?
Your Gloucester break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.