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Your Gwynn Vacation

Enjoy amazing adventures when you book a vacation package to Gwynn. Whether you're a foodie, history buff or just a traveler who loves discovering new places, there's something for everyone in this interesting city. Need some inspiration on what to do or see first during your trip to Gwynn? Check off well-known attractions such as Gwynns Island Musuem. Stop daydreaming and start doing. Check out the wide range of options on Expedia today and finally put your Gwynn vacation plans into gear!

The Latest Gwynn vacation packages

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games
Griffin Hotel, an official Colonial Williamsburg Hotel
Club Wyndham Kingsgate
The Colonies at Williamsburg
Hilton Vacation Club Greensprings Williamsburg
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Discover the most popular places to visit in Gwynn

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! (189 reviews)
"We loved the cottage! The bay was so close that even when you were inside you felt like you were on the beach. The sunsets were AMAZING. The neighbors were very quiet, the beach was private and the cottage was clean- leading to a nice, relaxing trip full of kayaking, fishing, reading on the beach ..."

Reviewed on Aug 8, 2025

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
$105 nightly
The price is $117 total per night from Sep 4 to Sep 5
$117 total
Sep 4 - Sep 5
Total includes taxes and 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
$134 nightly
The price is $149 total per night from Aug 21 to Aug 22
$149 total
Aug 21 - Aug 22
Total includes taxes and 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
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.

Things to do near Gwynn

Gwynn, Virginia, is a perfect destination for culture enthusiasts and outdoor lovers alike, offering a variety of activities such as exploring the scenic recreational areas, strolling along the boardwalk, and enjoying a round of golf. Visitors can engage in vacation tours, outdoor adventures, and beach vacations, making it ideal for day trips and well-planned vacation itineraries. Experience the beautiful landscapes and vibrant local culture during your stay in this charming coastal town.

Shopping

If you're up for a drive, Main Street Center, located 14 miles from Gwynn, offers a vibrant shopping experience with a mix of business and family vibes. Walter Reed Plaza and Shoppes at Gloucester, both 15 miles away, also provide great options for gifts and souvenirs.

Recreation

At the Golden Eagle Golf Club, enjoy a day of golfing surrounded by beautiful landscapes just 13 miles from Gwynn. Piankatank River Golf Club offers a similar outdoor experience, located 11 miles away. For a more relaxing vibe, visit Beaverdam Park, 14 miles away, perfect for unwinding in nature.

Adventure

Experience thrills at Water Country USA, a waterpark located 26 miles from Gwynn, featuring exciting slides and family-friendly attractions. For motorsport fans, Langley Speedway, 30 miles away, offers adrenaline-pumping races. Don't miss MagiQuest, an arcade adventure zone 26 miles from Gwynn, perfect for family fun and exploration.

Nightlife

In Gwynn, Virginia, enjoy a laid-back evening at the local taverns, where friendly locals gather for drinks and live music. For a cozy vibe, visit the nearby pubs that often feature open mic nights and regional brews, perfect for relaxing after a day of exploring.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Gwynn

Gwynn, Virginia, is perfect for a culture-themed beach vacation, offering stunning islands, beautiful beaches, and marinas to explore. Enjoy outdoor activities and immerse yourself in the local culture while discovering attractions that cater to your interests. Whether you're looking to relax by the shore or engage in adventure-filled experiences, Gwynn has something for every traveler. Don't miss the chance to explore the local attractions and make the most of your visit.

  • Gwynn's Island Museum: Immerse yourself in the rich history and culture of Gwynn's Island at this charming museum. Discover fascinating archaeological artifacts and learn about the island's unique anthropology, all while enjoying the local cultural vibes.
  • Deltaville Maritime Museum: Located only 3 miles from Gwynn, this maritime museum celebrates the region's maritime heritage. Explore exhibits that showcase the area's history, boat building, and fishing culture, offering a deep dive into local traditions.
  • Holly Point Nature Park: Just 3 miles away, this serene nature park provides a perfect escape into nature. Stroll along scenic trails, enjoy peaceful views of the water, and bask in the park's relaxing atmosphere.

Best time to go to Gwynn

The best time to visit Gwynn is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.2°F (4.0°C)Light RainMostly SunnyModerately LowSlightly Low
February42.1°F (5.6°C)Light RainMostly SunnyAverageSlightly Low
March48.0°F (8.9°C)Light RainMostly SunnyAverageSlightly Low
April57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
May66.6°F (19.2°C)Light RainMostly SunnyModerately HighAverage
June74.8°F (23.8°C)Light RainMostly SunnyModerately HighSlightly High
July79.5°F (26.4°C)Light RainMostly SunnyModerately HighSlightly High
August77.9°F (25.5°C)Light RainMostly SunnyAverageSlightly High
September72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
October62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
November51.3°F (10.7°C)Light RainMostly SunnyModerately LowAverage
December44.8°F (7.1°C)Light RainMostly SunnyModerately LowAverage

Tips to save on your trip to Gwynn

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Gwynn during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals from $370 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?
You can typically find lower rates and better availability in November, December and January. Take a look at our cheap Gwynn vacation packages and you could score some excellent off-season deals.
How many days is enough for Gwynn?
With a well-planned schedule, you can easily hit the top Gwynn sights in a few days. But if you want to discover lesser-known spots or go on day tours, consider 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.
Does Expedia offer Book Now, Pay Later Gwynn vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Gwynn vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.