Gwynn Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Find the Best Gwynn Vacation Packages
Gwynn Hotel Deals
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Grimstead
10/10 Exceptional! (196 reviews)
"We absolutely love staying here—it’s become a tradition for us to return year after year. From the moment we arrive, Cheri always makes us feel so welcome and goes above and beyond to ensure everything is perfect for our stay. The house itself is beautiful, spotless, and so well taken care of—it ..."
Reviewed on Sep 17, 2025
Hampton Inn Gloucester
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is ￥18,933 per night from Oct 26 to Oct 27
￥18,933
￥21,072 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (717 reviews)
"We stay here often, great place"
Reviewed on Sep 7, 2025
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is ￥17,191 per night from Oct 5 to Oct 6
￥17,191
￥19,134 total
Oct 5 - Oct 6
includes taxes & fees
7/10 Good! (640 reviews)
"Great"
Reviewed on Sep 13, 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.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
