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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was CA $1,330, price is now CA $1,058 per person
CA $1,058
per person
Dec 17 - Dec 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very good! (1,715 reviews)
All good.

Reviewed on Nov 7, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,517, price is now CA $1,265 per person
CA $1,265
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
We stayed for 4 nights and never received any room service to clean the room even after calling twice. Best we got was a maintenance man who came to the room with a garbage bag full of towels. Their excuse was that they were too busy with 300 check ins. It appeared like those that used Expedia to book a room was on the bottom of the priority list.

Reviewed on Nov 6, 2026

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was CA $1,668, price is now CA $1,428 per person
CA $1,428
per person
Dec 17 - Dec 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,569 reviews)

The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was CA $1,579, price is now CA $1,354 per person
CA $1,354
per person
Dec 17 - Dec 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.6/10 Excellent! (1,330 reviews)

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,730, price is now CA $1,500 per person
CA $1,500
per person
Dec 17 - Dec 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)

Ready to book your vacation to Gwynn?

 

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Gwynn Hotel Deals

Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead VA
10/10 Exceptional! (238 reviews)
"This charming cottage has a spectacular water view, small private beach and very attractive and comfortable inside furnishings. I was particularly looking for a place we could kayak from easily, and could bring our Golden Retriever Beau, who loves the water.This cottage supplies everything you need ..."

Reviewed on Oct 29, 2026

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Waterfront Cottage w Private Beach on Chesapeake Bay!
Gwynn's Island Gem | Private Beach & Bay Views

Gwynn's Island Gem | Private Beach & Bay Views

Hudgins VA
10/10 Exceptional! (6 reviews)
"We ABSOLUTELY loved our stay here. Beautiful views, peaceful, accommodating...it was all of the things. The rooms were spacious, the master bed was nothing short of amazing! So comfortable!The deck needs a little attention, but it certainly served it's purpose, and we enjoyed sitting out at night ..."

Reviewed on Sep 22, 2026

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Gwynn's Island Gem | Private Beach & Bay Views
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 CA $119 per night from Dec 7 to Dec 8
CA $119
CA $133 total
Dec 7 - Dec 8
includes taxes & fees
Holiday Inn Express Gloucester by IHG
See all 357 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.
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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.
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Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals from CA $1,058 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.