Gloucester Vacations from $274

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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.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Save 100% on your flight
per person
Oct 14 - Oct 18
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
9.6/10 Exceptional! (92 reviews)
Great place to stay. Pete is a great host, easy check in great communication, pinball machines and games in the rooms really great. Quick drive to some good dining.

Reviewed on Jun 10, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Save 100% on your flight
per person
Oct 14 - Oct 18
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
9.2/10 Wonderful! (1,070 reviews)
Nice hotel if going to a show at the amphitheater. Within walking distance.

Reviewed on Jul 30, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Save 100% on your flight
per person
Oct 14 - Oct 18
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
8.4/10 Very Good! (1,008 reviews)
Hotel amenities were good, however, restaurants food wasn't that good. No microwave in our room made it inconvenient for warming up leftovers from other restaurants.

Reviewed on Jul 28, 2025

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

2.5 out of 5
Short Pump
Save 100% on your flight
per person
Oct 14 - Oct 18
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Richmond (RIC)
8.6/10 Excellent! (1,751 reviews)
Room clean, had some repairs issues. Clean towel policy. Simple breakfast choices. Mostly underground parking. Overall positive experience, would stay again.

Reviewed on Jul 31, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Sep 17 - Sep 21
found 16 hours ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
10/10 Exceptional! (9 reviews)
We had a wonderful, relaxing weekend stay at Warner Hall. The hosts Christina and Fred were very welcoming and the house and property is amazing. The house (more like mansion) and rooms are huge and comfortable with lots of space for reading a book, etc. We really enjoyed the morning coffee and tea service brought straight to our rooms. We felt like royalty! There's so much history to the Warners, we had no idea. Definitely highly recommend this place if you're looking for a break from being busy busy.

Reviewed on Jul 9, 2025

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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 Zanoni. Experience the festivals and art scene in this family-friendly area.

Gloucester Museum of History

Gloucester Hotel Deals

Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $112 total per night from Aug 17 to Aug 18
$112 total
Aug 17 - Aug 18
Total includes taxes and fees
9/10 Wonderful! (703 reviews)
"Beautiful hotel. Friendly staff."

Reviewed on Jul 22, 2025

Hampton Inn Gloucester
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
$109 nightly
The price is $124 total per night from Aug 12 to Aug 13
$124 total
Aug 12 - Aug 13
Total includes taxes and fees
8.8/10 Excellent! (2,894 reviews)
"I would love to come back anytime this my place right here"

Reviewed on Jul 28, 2025

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
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $168 total per night from Aug 10 to Aug 11
$168 total
Aug 10 - Aug 11
Total includes taxes and fees
8.8/10 Excellent! (1,485 reviews)
"We really enjoyed our one night stay and the staff were all fantastic. Breakfast has limited seating so be sure to get there early. Internet/wifi was spotty but was possibly due to stormy weather in the area."

Reviewed on Jul 29, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
See all 2,232 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

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 $274 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.