Gwynn Vacation Packages
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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!
Top Gwynn Vacation Deals
Price found within the past 48 hours. Click for updated prices.
King’s Creek Resort by Spinnaker
CA $1,005
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (267 reviews)
We were in 203 b I cannot tell you the street. We were in a one bedroom. I assume you only get the photos that you're shown in a two bedroom. But it was enough for the two people that stayed. My only issue was, there was a connecting door between the two suites. That door must connect to the kitchen area of the other suite. Because we could hear them like they were talking to us in our own space. We liked the neighbors. So it wasn't a neighbor complaint, just a thin connecting door complaint. Because the connecting door is right by your bedroom.
Now on to the positives. Check in was super quick. The room has everything you need to cook, relax and chill on the balcony. You get a full stove and a washer dryer combo in the unit. You are 2 minutes from Water Country and 10 minutes from Busch Gardens. There was so much to do at the resort. We just didn't have time to do it with going to the parks. Multiple pools, a game room playground et. Cetera. We will be back.
Reviewed on Aug 23, 2026
Four Points by Sheraton Richmond
North Chesterfield
CA $1,191
per person
Nov 15 - Nov 21
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,007 reviews)
Breakfast isn't free so prepare for that which was okay because we didn't need to eat it. Feel like the walls were kind of thin but other than that everything was great
Reviewed on Aug 22, 2026
Country Inn & Suites by Radisson, Richmond West at I-64, VA
Laurel
CA $1,021
per person
Nov 15 - Nov 21
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8/10 Very good! (1,015 reviews)
Very nice and relaxful stay. Staff was great. Would definitely stay again.
Reviewed on Aug 23, 2026
Ready to book your vacation to Gwynn?
Gwynn Hotel Deals
Gwynn's Island Gem | Private Beach & Bay Views
Hudgins VA
10/10 Exceptional! (3 reviews)
"We enjoyed our stay. Home was clean with good A/C and the bay breeze also nice outside. My wife really loved the sunrise. The island is a nice quiet get away spot, but still within 10-40 min. or so of some nice small town's or a day trip to York / Williamsburg. Very nice sandy beach, just would have ..."
Reviewed on Jul 27, 2026
Waterfront Cottage w Private Beach on Chesapeake Bay!
Grimstead VA
10/10 Exceptional! (228 reviews)
"The Cottage at Gwynn Island is truly magical. Such a wonderful setting on the bay with a private beach to swim with our doggies.Our host was extremely kind and we look forward to visiting again soonSincerely Joyce and Gary"
Reviewed on Jul 26, 2026
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Fully refundable
CA $127
CA $141 total
Sep 21 - Sep 22
includes taxes & fees
7.2/10 Good! (731 reviews)
"No complaints. Staff was great. Breakfast was great. Great location for our needs."
Reviewed on Aug 21, 2026
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 exploring the galleries in Gwynn's Island Museum during your trip to Piankatank. Amble around the area's marina or experience its festivals.
Frequently asked questions
How much does a Gwynn vacation package cost?
Offering excellent value package deals from CA $1,005 on Expedia, you'll be surprised at how little a vacation to Gwynn costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Gwynn?
If you're hoping to book a cheap Gwynn vacation package, consider travelling in January, February and November. You'll usually find lower prices on hotels and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Gwynn?
To get the most out of your Gwynn vacation, we suggest staying for 3 days. Split your time between discovering Deltaville Maritime Museum, Holly Point Nature Park and other must-see attractions, in addition to experiencing neighbourhoods like Piankatank and Moon. If you've got some spare time, add a tour or day trip to your Gwynn vacation itinerary.
How to find the best Gwynn package deals?
Begin your search for a Gwynn package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Gwynn package deal right away, simply change your dates and search again. Bear in mind 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?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Gwynn vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Gwynn?
Secure incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Gwynn escape.
How to plan a trip to Gwynn?
- Choose when to travel: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to vacation in Gwynn.
- Budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may crop up during your trip to Gwynn.
- Determine how many days away: Start by listing all the activities and sights you'd like to get to in Gwynn. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Gwynn vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
