Winfield Vacations from $264

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The Latest Winfield vacation packages

Price found within the past 48 hours. Click for updated prices.
River Terrace Resort & Convention Center

River Terrace Resort & Convention Center

3.5 out of 5
Downtown Gatlinburg
Save 100% on your flight
Price was $432, price is now $264 per person
$264
per person
Dec 17 - Dec 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
7.8/10 Good! (1,002 reviews)

Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Price was $645, price is now $358 per person
$358
per person
Jan 21 - Jan 24
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
8.4/10 Very Good! (1,388 reviews)

Hotel Indigo Gatlinburg Downtown by IHG

Hotel Indigo Gatlinburg Downtown by IHG

3.5 out of 5
Downtown Gatlinburg
Price was $618, price is now $377 per person
$377
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
9.6/10 Exceptional! (789 reviews)
Excelente servicio. Personas muy amables. El Hotel 100% recomendado.

Reviewed on Nov 9, 2026

Gatlinburg Town Square

Gatlinburg Town Square

2.5 out of 5
Price was $531, price is now $337 per person
$337
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
8/10 Very Good! (1,493 reviews)

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Price was $1,226, price is now $793 per person
$793
per person
Dec 24 - Dec 27
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
9/10 Wonderful! (361 reviews)

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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
$90 nightly
The price is $99 total per night from Dec 1 to Dec 2
$99 total
Dec 1 - Dec 2
Total with taxes and 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
$114 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and 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
$111 nightly
The price is $123 total per night from Dec 6 to Dec 7
$123 total
Dec 6 - Dec 7
Total with taxes and 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.

Find the Best Winfield Vacation Packages

Winfield Essential Information

Language
English
Currency
U.S dollars
Population
950

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Frequently asked questions

How much does a Winfield vacation package cost?
You can snap up a vacation package to this top destination from $264 on Expedia. But how much your vacation to Winfield costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winfield?
You can generally find reduced prices and greater availability in January, October and December. Check out our cheap Winfield vacation packages and you could score some great off-season deals.
How many days is enough for Winfield?
Typically, a handful of days is enough to tick off the major sights during your Winfield vacation. But if you want to have some time to unwind or take day trips, consider extending your itinerary.
How to find the best Winfield package deals?
Use Expedia's filters to help you find some terrific Winfield package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Winfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Winfield vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customize your Winfield trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winfield?
If you've got your Winfield vacation dates finalized, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
If you're like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Winfield break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.