Gwynn Holidays

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Gwynn Holiday

Our pick of the best Gwynn Hotel Deals

Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail w 1/2 Labor Day weekend!

Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail w 1/2 Labor Day weekend!

Grimstead VA
10/10 Exceptional! (225 reviews)
"Our third summer here, and have never been disappointed. The sunsets are an amazing treat every evening."

Reviewed on 23 June 2026

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Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail w 1/2 Labor Day weekend!
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
The price is NZ$211 per night from 19 July to 20 July
NZ$211
19 July - 20 July
includes taxes & fees
7.2/10 Good! (709 reviews)
"The hotel was okay. However, the property is a little dated. Also, I didn’t have a sitting chair in the room. Finally, and I have never experienced this before; but there were no cups in the room!"

Reviewed on 20 June 2026

Holiday Inn Express Gloucester by IHG
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
Fully refundableReserve now, pay when you stay
The price is NZ$868 per night from 6 July to 7 July
NZ$868
6 July - 7 July
includes taxes & fees
The Tides Inn
See all 365 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.

Stay near popular Gwynn attractions

Gwynn's Island Museum

10.0/10 (2 reviews)
You can spend an afternoon studying the exhibits at Gwynn's Island Museum in Piankatank. Amble around the area's marina or experience its festivals.
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Frequently asked questions

How much does a Gwynn holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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-organised 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 holiday 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 holiday as a package?
You can enjoy significant savings on your next Gwynn escape by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday 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 holiday. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your accommodation and airfare: After you've nailed down your travel dates and duration, book the ideal Gwynn holiday package for you.

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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.