Winfield Vacations from $508

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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
Price was $834, price is now $508 per person
$508
per person
Dec 25 - Dec 28
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Knoxville (TYS)
7.8/10 Good! (1,002 reviews)
Donna is a doll!!!! She is the sweet person ever! Yall must stop and talk to her! Very knowledgeable!!

Reviewed on Oct 31, 2026

Smokies Sanctuary

Smokies Sanctuary

5 out of 5
Price was $2,004, price is now $1,181 per person
$1,181
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Knoxville (TYS)
10/10 Exceptional! (1 review)
Beautiful place. Amazing views. I would stay here every time. The property owners were very nice and answered any questions I had. They made sure I was taken care of. If you are in pigeon forge or gatlinburg, stay here.

Reviewed on Jul 17, 2026

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Save 100% on your flight
Price was $1,468, price is now $952 per person
$952
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9/10 Wonderful! (361 reviews)
Me encanto todo muy limpio y comodo paamos un fin de semana increible

Reviewed on Oct 29, 2026

Mountain Meadows

Mountain Meadows

2.5 out of 5
Price was $869, price is now $566 per person
$566
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
8.4/10 Very Good! (19 reviews)
The place all together was very quiet and no issues. My main thing is the AC. We had an upstairs/downstairs unit and the upstairs would not cool, we all had to sleep with no blankets & that’s an awful nights sleep. The phone number on google was not up to date so trying to get ahold of somebody to figure out check in was a hassle & the number it has on the building to call if you check out before the building is open is not a working number also. The place was very cute, very quiet, & the staff is VERY FRIENDLY but for a family of six, we probably won’t be staying here again.

Reviewed on Oct 4, 2026

Hotel Indigo Gatlinburg Downtown by IHG

Hotel Indigo Gatlinburg Downtown by IHG

3.5 out of 5
Downtown Gatlinburg
Price was $1,053, price is now $718 per person
$718
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9.6/10 Exceptional! (789 reviews)
We stayed one night. The location is perfect! Just a few minutes walk from Anakeesta and Ripley’s aquarium. Heated pool. Free parking. Not sure what the extra charge from the bar was for, as I paid for my one drink in cash. But otherwise, I would stay again & recommend this hotel.

Reviewed on Oct 30, 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
$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! (1,002 reviews)
"Beautiful area comfortable beds with spacious cabins. The cabins are 2 per building like a duplex and you can hear everything in the other cabin. And as most state parks do, they won’t let you in a minute early."

Reviewed on Oct 30, 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
$113 nightly
The price is $126 total per night from Dec 1 to Dec 2
$126 total
Dec 1 - Dec 2
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
$111 nightly
The price is $123 total per night from Nov 15 to Nov 16
$123 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (906 reviews)
"Great location to satisfy our one night stay, staff was personable and professional and the room was very clean and comfortable. A very good overall customer experience, thanks!"

Reviewed on Oct 26, 2026

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 $508 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.