Photo by Nawa Aseen

Find Cheap Hotels in Winchester, KY

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Cheap Hotels

This weekend
Next weekend

Our top choices for Winchester cheap hotels

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (527)
"The room was clean, bed was very comfortable and the staff couldn’t have been nicer!"
United States
Stevy
The price is ¥13,725
¥15,130 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Lexington East - Winchester by IHG

Red Roof Inn Winchester - Lexington East

Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (587)
"Great stay"
United States
Walter
The price is ¥9,718
¥10,712 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Red Roof Inn Winchester - Lexington East

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1002)
"Clean room, friendly and fast check in service and had a great nights sleep "
United States
Cynthia
The price is ¥11,267
¥12,422 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Winchester Hotel

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353)
"The pool had no water. There was no pool available. There wasn't any hot water in our room. Unless you run it for 15/20 min"
United States
teresa
The price is ¥11,434
¥12,605 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (772)
"The room was all that we expected very good. Staff was very friendly."
United States
LEROY
The price is ¥12,595
¥13,884 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Baymont by Wyndham Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (452)
"Would stay there again"
United States
Patricia
The price is ¥18,726
¥20,644 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn Winchester

Value Stay

Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (126)
"Awesome rooms and service"
United States
Brandon
The price is ¥10,450
¥11,520 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Value Stay

avid hotel Lexington - Hamburg Area by IHG

avid hotel Lexington - Hamburg Area by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (880)
"Great stay"
United States
Amy
The price is ¥10,918
¥12,673 total
includes taxes & fees
Jan 23 - Jan 24, 2026
avid hotel Lexington - Hamburg Area by IHG

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1215)
"Love love love this hotel. "
United States
Kirsten
The price is ¥14,109
¥16,377 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North
3.0 star property
Lexington
8.6 out of 10, Excellent, (1008)
"Perfect for overnight stay! Great breakfast "
Canada
Lawrence
The price is ¥11,074
¥12,854 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Fairfield Inn & Suites by Marriott Lexington North
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.

Top Winchester Hotel Reviews

Frequently asked questions

What is Winchester like for travelers on a budget?
Winchester has cheap accommodation options and a variety of places to visit, making it a budget-friendly vacation choice. You can find ways to save money while getting to know this destination, which is home to attractions like Bluegrass Heritage Museum, Winchester Opera House, and Clark County Courthouse.
When is the best time for a budget trip to Winchester?
Weather will likely play an important role when you plan your trip to Winchester, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Winchester is 56 inches.
What is there to see and do in Winchester?
Winchester is known for its dining options and offers things to see and do without spending a fortune. You can budget for the local attractions that interest you most, and then plan some activities that cost little or nothing at all. If you're eager to get outdoors, you can enjoy the natural setting at College Park, GRCHS Baseball Field, or Community Park.
How can I get to Winchester and get around on a budget?
Scoping out the transportation options in Winchester is a smart way to keep your trip affordable. The closest airport is Blue Grass Airport (LEX), 23 mi (37.1 km) away. Winchester might not have many public transit options so renting a car could be an economical alternative to explore more of the area.