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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was CA $1,640, price is now CA $1,263 per person
CA $1,263
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,006 reviews)
The staff were very helpful and nice

Reviewed on Aug. 25, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was CA $1,890, price is now CA $1,456 per person
CA $1,456
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,011 reviews)
Love the water park for the kids and nice and clean accomidations

Reviewed on Aug. 25, 2025

Westgate Williamsburg

Westgate Williamsburg

2.5 out of 5
Price was CA $2,383, price is now CA $1,899 per person
CA $1,899
per person
Oct 12 - Oct 18
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
No reviews
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was CA $1,744, price is now CA $1,399 per person
CA $1,399
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,644 reviews)
Very nice property. Not too far from W&M campus (about 10 minute drive). Very clean and comfortable. Would definitely stay here again.

Reviewed on Aug. 25, 2025

Holiday Inn Club Vacations Williamsburg Resort by IHG

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5
Price was CA $1,652, price is now CA $1,338 per person
CA $1,338
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (486 reviews)
Very family friendly. Very close to anything you need without being overcrowded. Staff were great. Extremely clean place to stay.

Reviewed on Aug. 24, 2025

Ready to book your vacation to Gwynn?

 

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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! (192 reviews)
"Very relaxing vacation with beautiful view. Very clean and well stocked with everything needed."

Reviewed on Aug. 18, 2025

Get rates
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
The price is CA $145 per night from Sep 4 to Sep 5
CA $145
CA $162 total
Sep 4 - Sep 5
includes taxes & fees
7/10 Good! (629 reviews)
"Comfortable, clean, and convenient"

Reviewed on Aug. 19, 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
The price is CA $187 per night from Sep 1 to Sep 2
CA $187
CA $208 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (713 reviews)
"Everything was wonderful. The stairwell had a funny odor. I suggest trying to make that a more delightful smell! Also the air conditioner in the room was so loud I could hardly hear the tv"

Reviewed on Aug. 25, 2025

Hampton Inn Gloucester
See all 335 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.
All Inclusive Vacations
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Beach Vacations
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Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals from CA $1,263 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.