Gloucester Vacations from $449

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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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$449
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
8.8/10 Excellent! (1,872 reviews)
The breakfast had eggs every morning. However the cheese combinations were not tasty. They only consisted of bacon bits one morning. They expect you to think the various coffee cakes were prepared in house, however they were never warm to the touch and often consisted of an entire top layer of pure sugar and bottom with no taste. Waffles were also store bought and had no taste. Room keys had to be replaced daily, since they never worked to open our door. Site amenities like mini golf, corn hole, table tennis were stated as no cost, but then charged me $20 per day for them even though we did not use them. A package was delivered to my hotel room and left in the hallway,and discarded by cleaning staff. I found a pair of socks at the foot of the bed from a previous room guest. previous

Reviewed on Aug 16, 2026

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
$450
per person
Sep 25 - Sep 27
found 8 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.6/10 Excellent! (1,002 reviews)
The hotel is historic and updates made are just enough to make for an ok stay. If a family needs a full kitchen, washer/dryer, then this may be the hotel for you. The room was clean, but if you reserve a room with a king bed and queen pull out bed, beware you may not get a good night's sleep in the pull out bed. The bed was very plastic material like and hard. The hallways of the hotel smelled of mold and dampness and very dated. The pool and fitness room seemed nice from a distance; however, we didn't have time to utilize. The arcade room that is advertised is pay to play and not included within the amenities. Staff seemed very annoyed at questions and did not give off a very hospitable vibe. We stayed one night and switched hotels for the second night of our stay in Williamsburg.

Reviewed on Aug 8, 2026

Wedmore Place

Wedmore Place

Save 100% on your flight
$695
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
The help was extremely friendly and helpful. Pool is not fancy but at the perfect temperature. Floors are old and creaky but add to the overall atmosphere of the place. Daily breakfast was more than enough to start the day.

Reviewed on Aug 15, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg
Save 100% on your flight
$863
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (848 reviews)
Kingsmill Resort

Kingsmill Resort

Kingsmill
$746
per person
Oct 18 - Oct 23
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,013 reviews)
It was a mixed experience. The grounds are beautiful and really well maintained and the facilities are excellent - really nice pool, extensive tennis courts with a club feel and beautiful (but expensive) golf courses along with a good driving range. The staff were very friendly. So far so good. However, the properties are very dated and so not a very enjoyable experience to stay in them. They are clean but they get limited sunlight so have a dingy feel and you wouldn’t want to spend much time in them. The fixtures and fittings are old - even the hairdryer was ancient and smoked - the kitchen had a borderline musty smell - it needs a very big overhaul. Because of the size of the property they offer a golf cart service to get to the various places but this required calling for a cart but for whatever reason the phone numbers dont work with any UK phone. In addition there were no phones in the units to be able to contact reception /concierge. So it was problematic getting to places particularly given the heat. It was also a bit odd that everything shut down at 9pm $49 plus sales tax daily additional charge applied, but for whatever reason i could not fathom

Reviewed on Aug 16, 2026

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Stay near popular Gloucester attractions

Beaverdam Park

Explore Beaverdam Park's 635-acre reservoir through hiking trails and tranquil waterways. Rent a boat to fish for largemouth bass or observe diverse wildlife from the park's scenic overlooks.
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Gloucester Museum of History

9.0/10 (4 reviews)
Housed in the 1770 Botetourt Building, this museum displays Gloucester County's rich past through 3,000+ artifacts. Explore American Revolution and Civil War exhibits while enjoying free admission to this historic treasure.
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Shoppes at Gloucester

You can do some window-shopping at Shoppes at Gloucester during your trip to Gloucester. Experience the festivals and art scene in this family-friendly area.
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Middle Peninsula State Park

10.0/10 (1 review)
Virginia's first state park dedicated to Native American history showcases the legacy of the Powhatan Confederacy. Explore interpretive exhibits, scenic trails, and diverse habitats from tidal marshes to mixed forests.
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Rosewell Ruins

6.0/10 (2 reviews)
These haunting brick ruins were once America's grandest colonial mansion, built by the Page family in 1725. Explore the massive chimneys and remaining walls while overlooking the serene York River landscape.
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Thousand Trails Beach Park

This 280-acre waterfront campground offers shaded RV sites and cabins along Virginia's Piankatank River. Enjoy fishing, mini-golf, and seasonal events while exploring nearby historical attractions in Gloucester.
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Main Street Center

You can do some window-shopping at Main Street Center during your stay in Gloucester. Experience the festivals and art scene in this family-friendly area.
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Gloucester Golf Club

This classic 9-hole parkland course has welcomed golfers of all skill levels since 1929. Enjoy the relaxed atmosphere while navigating well-maintained fairways and challenging greens at this local favorite.
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Gloucester Hotel Deals

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

6639 Forest Hill Ave Gloucester VA
Fully refundable
$95 nightly
$106 total
Sep 10 - Sep 11
Total with taxes and fees
Holiday Inn Express Gloucester by IHG
Vacation Village At Williamsburg

Vacation Village At Williamsburg

4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
$92 nightly
$105 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (2,768 reviews)
"The unit was very clean and spacious. It's close to lots eating place and down town Williamsburg."

Reviewed on Aug 16, 2026

Vacation Village At Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$92 nightly
$105 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (3,773 reviews)
"I love if"

Reviewed on Aug 16, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
See all 2,211 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 $449 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.