Gloucester Vacations from $315
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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.
The Colonies at Williamsburg
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
There was a problem with some of the rooms at the Colonies so we had to move to their sister resort down the road. Due to the inconvenience they upgraded our room to a very nice 2 bedroom suite and gave us a complimentary 2 night stay for the future.
Reviewed on Jul 5, 2025
Linden Row Inn
Downtown Richmond
Save 100% on your flight
per person
Sep 15 - Sep 20
found 7 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9.2/10 Wonderful! (1,060 reviews)
Everything related to the hotel was awesome. Very old and charming building, I could stay there for years. No laundry or parking on site though. Only thing that was irritating was panhandling in the area, not that it’s the hotel’s fault.
Reviewed on Jun 25, 2025
Barsala At Sphere Apartments
Save 100% on your flight
per person
Sep 15 - Sep 20
found 7 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
9/10 Wonderful! (12 reviews)
Overall this property was a good place to stay so we could spread out and have extra room for our trip. Communication was fine and checkin instructions were very detailed. I cannot give it 5 stars however. The shower curtain and shower were dirty. There were stains on the bed linens and the comforter as well as a hole in the comforter. The property also charges $5/day for parking which was not disclosed in the original price. The exterior of the property had a dog area and people did not clean up after their dog — this was also the area we were required to park.
Reviewed on Jun 29, 2025
Club Wyndham Kingsgate
Save 100% on your flight
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
8.8/10 Excellent! (1,015 reviews)
The 2 Bedroom we stayed in was pretty spacious for our family of 3. The activity center was walkable to enjoy the pool, gameroom, and mini golf.
Reviewed on Jul 5, 2025
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.
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 Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
$111 nightly
The price is $124 total per night from Jul 13 to Jul 14
$124 total
Jul 13 - Jul 14
Total includes taxes and fees
7/10 Good! (616 reviews)
"Sunday we didn't have hot water so we couldn't take showers."
Reviewed on Jun 30, 2025
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $134 total per night from Jul 13 to Jul 14
$134 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (2,797 reviews)
"The area was peaceful. The room was clean and huge! Front desk could use a few more people working since it took us 20mins to check in. Wifi was ok. Overall would stay again for vacation."
Reviewed on Jul 4, 2025
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr, Williamsburg, VA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $127 total per night from Jul 7 to Jul 8
$127 total
Jul 7 - Jul 8
Total includes taxes and fees
8.8/10 Excellent! (1,420 reviews)
Woodlands
"This is our second stay at the Woodlands, last time was December 2024. The convenience to the Visitor Center, downtown and shuttle is AMAZING. We have walked numerous times but this time took the shuttle since it was raining. 1000% recommend because of this. The breakfast in the morning was great ..."
Reviewed on Jul 3, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.