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.
Eagle Inn by Hotel O Richmond Midlothian Turnpike

Eagle Inn by Hotel O Richmond Midlothian Turnpike

2.5 out of 5
Midlothian
Price was CA $775, price is now CA $706 per person
CA $706
per person
Aug 28 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
6/10 (24 reviews)
Booked room thru Expedia. Expedia charged my card $158. Get to hotel. They say room is booked but they only received $38. They said I have to pay the balance. I left. Still awaiting refund.

Reviewed on Jun 11, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,047, price is now CA $919 per person
CA $919
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,790 reviews)
ty

Reviewed on Jul 9, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $1,136, price is now CA $1,002 per person
CA $1,002
per person
Aug 20 - Aug 24
found 17 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
8.8/10 Excellent! (1,373 reviews)
Hotel was a bit run down, elevators had noticeable scratches Toile Toilet not clean Not staying here again

Reviewed on Jul 8, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,409, price is now CA $1,244 per person
CA $1,244
per person
Sep 10 - Sep 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,010 reviews)
Beautiful! Lots to do with chidren.

Reviewed on Jul 8, 2026

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
Price was CA $905, price is now CA $815 per person
CA $815
per person
Aug 29 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,003 reviews)
Clean

Reviewed on Jul 9, 2026

Ready to book your vacation to Gwynn?

 

Choose your dates

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
Get rates
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
Fully refundable
The price is CA $132 per night from Aug 3 to Aug 4
CA $132
CA $147 total
Aug 3 - Aug 4
includes taxes & fees
7.2/10 Good! (713 reviews)
"My room smelled of mold and mildew.. My bedding felt damp. Staff quickly exchanged linens, but next night, those linens felt damp also. Room smelled moldy the entire trip. Other then that it was fair."

Reviewed on Jul 6, 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 CA $559 per night from Jul 28 to Jul 29
CA $559
CA $675 total
Jul 28 - Jul 29
includes taxes & fees
The Tides Inn
See all 366 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.
See properties

Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals from CA $706 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.

Explore a world of travel with Expedia

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