Winfield Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Winfield

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

3.5 out of 5
7351 Hwy. 90, Williamsburg, KY
8.4/10 Very Good! (1,000 reviews)
Room 316 *****
"Room 316 was excellent all the way around. The falls destination was outstanding. Front desk very helpful and friendly."

Reviewed on 15 Jul, 2025

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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 S$144 per night from 27 Jul to 28 Jul
S$144
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (985 reviews)
"Very friendly staff. Nice breakfast. Check in very seamless."

Reviewed on 7 Jul, 2025

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 S$173 per night from 27 Jul to 28 Jul
S$173
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (704 reviews)
"Great overall. High pressure water even if we were on 3rd floor. Everything is nice and clean. The only small complain (which didn't affect us much) is complexity to join the wifi, you need to click multiple buttons and input some of your information to join the free hotel wifi."

Reviewed on 11 Jul, 2025

Hampton Inn Williamsburg
See all 505 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.

Frequently asked questions

How much does a Winfield holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday 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?
The off-season is the best time to visit Winfield if you're trying to save. Another tip for getting cheap Winfield holiday packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Winfield?
The ideal duration of your Winfield holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to hit all the main attractions and discover some hidden spots along the way.
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 holiday package as soon as possible.
Is it cheaper to book a Winfield holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customise 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 holiday package to Winfield?
If you've got your Winfield holiday 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 travelling on a whim.
How to plan a trip to Winfield?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Winfield.
  2. Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to flights and experiences. Your hotel will probably be the largest expense during your trip to Winfield.
  3. Work out your trip length: Consider how long you want to spend discovering Winfield. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Winfield holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.