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Hotels in Winchester, KY

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Travel insights for hotels in Winchester

Use our HotelsCombined data-powered tips to help you find your next hotel in Winchester.

What is the cheapest month to book a hotel in Winchester?

The cheapest month to book a hotel in Winchester is January ($82). Conversely, the most expensive month to stay in Winchester is May ($139).

What is the cheapest day to stay in a hotel in Winchester?

The cheapest day to stay in Winchester is Tuesday ($92). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $134.
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Cheapest hotels in Winchester, KY

Discover affordable stays in Winchester, KY that provide a quality experience without breaking the bank. Hotels in Winchester, KY can be found for as low as $67 per night. There is currently one property in Winchester, KY that can be booked for this price. Baymont by Wyndham Winchester is one of the hotels that can be booked for the lowest price in Winchester, KY. Price data was last updated on August 9, 2025
For those on a budget, these are the cheapest hotels available in Winchester for the selected dates. Consider alternative dates if you're able to compare prices.
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Drive, Winchester, KY, United States
1.5 mi from city centre
Pool
Free Wi-Fi
Parking
$67
Avg. per night
View Deal
Red Roof Winchester - Lexington East
Red Roof Winchester - Lexington East

Red Roof Winchester - Lexington East

1100 Interstate Drive, Winchester, KY, United States
1.5 mi from city centre
Free Wi-Fi
$69
Avg. per night
View Deal
Comfort Inn
Comfort Inn

Comfort Inn

5250 Revilo Road, Winchester, KY, United States
2.1 mi from city centre
Free Wi-Fi
Air Conditioning
Pool
$77
Avg. per night
View Deal
Best Western Winchester Hotel
Best Western Winchester Hotel

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States
1.5 mi from city centre
Free Wi-Fi
Parking
$110
Avg. per night
View Deal
Holiday Inn Express - Lexington East - Winchester By IHG
Holiday Inn Express - Lexington East - Winchester By IHG

Holiday Inn Express - Lexington East - Winchester By IHG

100 Winchester Plaza, Winchester, KY, United States
2.2 mi from city centre
Pool
Free Wi-Fi
Parking
$123
Avg. per night
View Deal
Hampton Inn Winchester
Hampton Inn Winchester

Hampton Inn Winchester

1025 Early Drive, Winchester, KY, United States
1.5 mi from city centre
Free Wi-Fi
Parking
$147
Avg. per night
View Deal

Hotel prices in Winchester, KY

Get a sense of the average price and most popular properties to stay in Winchester to help you budget for your trip accordingly. Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” badge are the most popular hotels in Winchester at attractive prices. Price data was last updated on August 9, 2025.
We've come across the following hotels in Winchester with different price and hotel class options. You'll also find the most popular and best value properties within each hotel class.
3 stars
Hampton Inn Winchester
Hampton Inn Winchester

Hampton Inn Winchester

1025 Early Drive, Winchester, KY, United States
$147
View Deal
2 stars and under
Red Roof Winchester - Lexington East
Red Roof Winchester - Lexington East

Red Roof Winchester - Lexington East

1100 Interstate Drive, Winchester, KY, United States
$69
View Deal
Comfort Inn
Comfort Inn

Comfort Inn

5250 Revilo Road, Winchester, KY, United States
$77
View Deal
Best Western Winchester Hotel
Best Western Winchester Hotel

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States
$110
View Deal
Holiday Inn Express - Lexington East - Winchester By IHG
Holiday Inn Express - Lexington East - Winchester By IHG

Holiday Inn Express - Lexington East - Winchester By IHG

100 Winchester Plaza, Winchester, KY, United States
$123
View Deal
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

960 Interstate Drive, Winchester, KY, United States
$67
View Deal

Other accommodations in Winchester

Find the perfect hostel, theme hotel, or vacation rental for your stay in Winchester, KY. There are 24 hotels in Winchester, KY and price data was last updated on August 9, 2025. The average price for a stay in Winchester, KY is $107/night.
Best Western Winchester Hotel
Best Western Winchester Hotel

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States
1.5 mi from city centre
Free Wi-Fi
Parking
$110
Avg. per night
View Deal
Holiday Inn Express - Lexington East - Winchester By IHG
Holiday Inn Express - Lexington East - Winchester By IHG

Holiday Inn Express - Lexington East - Winchester By IHG

100 Winchester Plaza, Winchester, KY, United States
2.2 mi from city centre
Pool
Free Wi-Fi
Parking
$123
Avg. per night
View Deal

Where to stay in Winchester

Explore different neighborhoods and areas within Winchester, KY to find the perfect location for your stay. Map data was last updated on August 9, 2025.
Scroll to and zoom in on the areas in Winchester you plan on visiting to find nearby properties. Clicking a property's name will unlock more information and allow you to book that particular hotel.

Facts about staying in Winchester, KY

Find useful tips and insights about staying in Winchester to help you make the most of your experience. FAQs were last updated on August 9, 2025.

  • What are the best hotels in Winchester?

    Winchester is home to many highly-rated hotels, one of which is Baymont by Wyndham Winchester, which has a current rating of 7.1. For other potential stays, consider Best Western Winchester Hotel and Holiday Inn Express - Lexington East - Winchester By IHG, which can also be great places to stay in Winchester.

  • How much is a cheap hotel in Winchester?

    HotelsCombined users have found cheap hotels in Winchester starting from $68 per night in the last 3 days.

  • What are some other cities to stay in when visiting Kentucky?

    In addition to Winchester, travelers opt to visit Louisville when visiting Kentucky. Maysville is also a popular choice to visit.

  • How many hotels are there in Winchester?

    In total, there are 24 hotels to choose from in Winchester, compared to 8,280 properties in Kentucky.

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Find better results for your stay in Winchester, KY

Consider these popular 3-star hotels in Winchester

Stay at one of these Winchester 3-star hotels that users have found on HotelsCombined.
Hampton Inn Winchester

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book hotels that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discount hotels quickly, including Hotels Under $50 and Hotels Under $100. Discover hotel discounts now and make your hotel reservation today.