Winfield Vacation Packages

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Top Winfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Price was CA $881, price is now CA $713 per person
CA $713
per person
Jan 13 - Jan 16
found 13 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Knoxville (TYS)
8.4/10 Very good! (1,388 reviews)

River Terrace Resort & Convention Center

River Terrace Resort & Convention Center

3.5 out of 5
Downtown Gatlinburg
Price was CA $1,241, price is now CA $767 per person
CA $767
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Knoxville (TYS)
7.8/10 Good! (1,002 reviews)
We have stayed here a few times its not a luxury hotel if thats what you are looking for. We like staying because of the location great for walking to everything. Price is cheap the rooms are dated I think they are working on upgrading them. Our room was clean thats what matters to me. We do alot of hiking when we are there.

Reviewed on Nov 9, 2026

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Price was CA $1,616, price is now CA $1,089 per person
CA $1,089
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Knoxville (TYS)
9/10 Wonderful! (361 reviews)

Reagan Resorts Inn

Reagan Resorts Inn

2 out of 5
Downtown Gatlinburg
Price was CA $1,433, price is now CA $1,091 per person
CA $1,091
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Knoxville (TYS)
8.6/10 Excellent! (1,759 reviews)

Gatlinburg Town Square

Gatlinburg Town Square

2.5 out of 5
Price was CA $1,115, price is now CA $891 per person
CA $891
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Syracuse (SYR) to Knoxville (TYS)
8/10 Very good! (1,493 reviews)
I would not have rented out the unit some of the receptacles didn’t work light switches were upside down and some lights didn’t work microwave barely worked had to heat things up 2-3 times had to slam the door to get it to latch shower didn’t have a knob had to push it with a brush towels were clean and enough of them overall I believe the unit was over priced for the condition

Reviewed on Nov 9, 2026

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Winfield Hotel Deals

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

3.5 out of 5
7351 Hwy. 90 Williamsburg KY
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Dec 2 to Dec 3
CA $114
CA $126 total
Dec 2 - Dec 3
includes taxes & fees
8.4/10 Very good! (1,004 reviews)
"Room was clean although the bathtub was in horrible condition. It was raining during our stay so we stayed in our room after about 6pm. The cable that was connected just buffered the entire time. Will definitely come back to the falls but will stay elsewhere."

Reviewed on Nov 8, 2026

Cumberland Falls State Resort Park
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
56 West Highway 92 Williamsburg KY
Fully refundable
The price is CA $161 per night from Dec 6 to Dec 7
CA $161
CA $179 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"The location of this property is very good and easy to access. Room was spacious and well-equipped except for a coffee maker. Our room happened to be just above the roof top for the front entrance leaving an unattractive view. Also, the darker shade on the window would not close leaving the room ..."

Reviewed on Oct 27, 2026

Holiday Inn Express Williamsburg by IHG
Hampton Inn Williamsburg

Hampton Inn Williamsburg

2.5 out of 5
530 Highway 92 W Williamsburg KY
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Dec 11 to Dec 12
CA $171
CA $190 total
Dec 11 - Dec 12
includes taxes & fees
Hampton Inn Williamsburg
See all 542 properties in Winfield
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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Frequently asked questions

How much does a Winfield vacation package cost?
You can pick up a vacation package to this top destination from CA $713 on Expedia. But how much your vacation to Winfield costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winfield?
Plan your trip for the off-season and you're likely to find cheap Winfield vacation packages. Bear in mind that school vacation periods and local festivals and events can have an impact on prices, so do a little research before booking.
How many days is enough for Winfield?
With a well-organized travel plan, you can easily visit the main Winfield sights in a few days. But if you want to discover hidden gems or take day trips, consider booking your Winfield vacation for longer.
How to find the best Winfield package deals?
Bagging a cheap Winfield package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Winfield package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Winfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Winfield vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Winfield?
If you have your Winfield vacation dates finalized, book as early as you can to score some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Winfield?

  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Winfield.
  2. Plan your budget wisely: As well as the cost of your accommodations, you should consider other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to Winfield.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Winfield. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Winfield vacation package.

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