Gwynn Vacations

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Find the Best Gwynn Vacation Packages

Gwynn Hotel Deals

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

Grimstead
10/10 Exceptional! (191 reviews)
Nice little spot with spectacular sunset views
"We stayed at the house and enjoyed the private beach. We caught lots of crabs. We went to the hatchery, which is on Gwen‘s Island and got to learn about the oyster farming. We booked a charter with dead rise, charters captain Trey taught us all about the crabbing industry in the oyster industry the ..."

Reviewed on Aug 12, 2025

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Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
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
The price is ￥15,518 per night from Sep 4 to Sep 5
￥15,518
￥17,272 total
Sep 4 - Sep 5
includes taxes & fees
7/10 Good! (626 reviews)
"Food could be little better"

Reviewed on Jul 24, 2025

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
The price is ￥19,848 per night from Aug 24 to Aug 25
￥19,848
￥22,092 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (710 reviews)
"Bed comfort and they changed out new towels almost every day"

Reviewed on Aug 5, 2025

Hampton Inn Gloucester
See all 337 properties in Gwynn
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.

Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Gwynn costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Gwynn?
January, February and November are great times to search for cheap Gwynn vacation packages. Opting to travel in quieter months means you can generally find reduced prices on hotels and flights.
How many days is enough for Gwynn?
With a well-organized schedule, you can easily hit the most popular Gwynn attractions in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Gwynn vacation for longer.
How to find the best Gwynn package deals?
Begin your search for a Gwynn package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Gwynn package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gwynn escape underway.
Is it cheaper to book a Gwynn vacation as a package?
You can enjoy significant savings on your next Gwynn escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Gwynn?
Score amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Gwynn trip.
How to plan a trip to Gwynn?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Gwynn.
  2. Set your budget: Factor in expenses like transportation, flights and meals when calculating how much to save for your trip to Gwynn. Then, select a hotel that works with your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide how long to go for: Now that you're up to speed on Gwynn, you can figure out the ideal length of your vacation. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Gwynn vacation package for you.

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