What are the best hotels in Winchester?

Winchester is home to many highly-rated hotels, one of which is Best Western Winchester Hotel, which has a current rating of 8.0. For other potential stays, consider Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester By IHG, which can also be great places to stay in Winchester.

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

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

How many hotels are there in Winchester?

In total, there are 20 hotels to choose from in Winchester, compared to 7,541 properties in Kentucky.

Winchester, KY Hotels: 20 Cheap Winchester, KY Hotel Deals

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 February ($83). Conversely, the most expensive month to stay in Winchester is October ($157).

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

The cheapest day to stay in Winchester is Tuesday ($88). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $121.

How far ahead should you book a hotel in Winchester?

Save money by booking a hotel at least 26 days before your trip to Winchester. The lowest price found when booking 26 days ahead was $64 per night.

Find deals

Cheapest hotels in Winchester, KY

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.

Show all 20 hotels

Comfort Inn

5250 Revilo Road, Winchester, KY, United States

2.1 mi from city centre

Free Wi-Fi

Air Conditioning

$59

Avg. per night

View Deal

Red Roof Inn Winchester - Lexington East

1100 Interstate Drive, Winchester, KY, United States

1.5 mi from city centre

Air Conditioning

$67

Avg. per night

View Deal

Baymont by Wyndham Winchester

960 Interstate Drive, Winchester, KY, United States

1.5 mi from city centre

Pool

Free Wi-Fi

Parking

$76

Avg. per night

View Deal

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

$94

Avg. per night

View Deal

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States

1.5 mi from city centre

Free Wi-Fi

Parking

$97

Avg. per night

View Deal

Hampton Inn Winchester

1025 Early Drive, Winchester, KY, United States

1.5 mi from city centre

Free Wi-Fi

Parking

$126

Avg. per night

View Deal

Hotel prices in Winchester, KY

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

1025 Early Drive, Winchester, KY, United States

$126

View Deal

2 stars and under

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States

$97

View Deal

Baymont by Wyndham Winchester

960 Interstate Drive, Winchester, KY, United States

$76

View Deal

Holiday Inn Express Lexington East - Winchester By IHG

100 Winchester Plaza, Winchester, KY, United States

$94

View Deal

Red Roof Inn Winchester - Lexington East

1100 Interstate Drive, Winchester, KY, United States

$67

View Deal

Comfort Inn

5250 Revilo Road, Winchester, KY, United States

$59

View Deal

Other accommodations in Winchester

Show all 20 stays

Best Western Winchester Hotel

1307 West Lexington Avenue, Winchester, KY, United States

1.5 mi from city centre

Free Wi-Fi

Parking

$97

Avg. per night

View Deal

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

$94

Avg. per night

View Deal

Where to stay in Winchester

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

What are the best hotels in Winchester?
Winchester is home to many highly-rated hotels, one of which is Best Western Winchester Hotel, which has a current rating of 8.0. For other potential stays, consider Baymont by Wyndham Winchester and Holiday Inn Express Lexington East - Winchester By IHG, which can also be great places to stay in Winchester.
What are some other cities to stay in when visiting Kentucky?
In addition to Winchester, travelers opt to visit Louisville when visiting Kentucky. Lexington is also a popular choice to visit.
How many hotels are there in Winchester?
In total, there are 20 hotels to choose from in Winchester, compared to 7,541 properties in Kentucky.

Find better results for your stay in Winchester, KY

3-Star Hotels

Complete Your Trip

Hotels in Kentucky

Consider these popular 3-star hotels in Winchester

Hampton Inn Winchester

Travel insights for hotels in Winchester

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

The cheapest month to book a hotel in Winchester is February ($83). Conversely, the most expensive month to stay in Winchester is October ($157).

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

The cheapest day to stay in Winchester is Tuesday ($88). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $121.

How far ahead should you book a hotel in Winchester?

Save money by booking a hotel at least 26 days before your trip to Winchester. The lowest price found when booking 26 days ahead was $64 per night.

Cheapest hotels in Winchester, KY

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.

Hotel prices in Winchester, KY

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

2 stars and under

Other accommodations in Winchester

Find the perfect hostel, theme hotel, or vacation rental for your stay in Winchester, KY. There are 20 hotels in Winchester, KY and price data was last updated on September 22, 2026. The average price for a stay in Winchester, KY is $107/night.

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 September 22, 2026.

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

What are the best hotels in Winchester?

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

How many hotels are there in Winchester?

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.

Complete your trip to Winchester

Search HotelsCombined for deals to complete your trip to Winchester and save big.

Explore these cities in Kentucky

Looking to explore Kentucky during your trip? These are other popular cities nearby that HotelsCombined users visit

Visit Top Destinations

These destinations around the world are some of the most sought after locations from our users

Cities our users search for

Based on the last 12 months of user searches on HotelsCombined

Hotels in Winchester, KY

Search and compare Winchester, KY hotels from hundreds of travel sites on HotelsCombined and save.

Travel insights for hotels in Winchester

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

The cheapest month to book a hotel in Winchester is February ($83). Conversely, the most expensive month to stay in Winchester is October ($157).

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

The cheapest day to stay in Winchester is Tuesday ($88). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $121.

How far ahead should you book a hotel in Winchester?

Save money by booking a hotel at least 26 days before your trip to Winchester. The lowest price found when booking 26 days ahead was $64 per night.

Cheapest hotels in Winchester, KY

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.

Hotel prices in Winchester, KY

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

2 stars and under

Other accommodations in Winchester

Find the perfect hostel, theme hotel, or vacation rental for your stay in Winchester, KY. There are 20 hotels in Winchester, KY and price data was last updated on September 22, 2026. The average price for a stay in Winchester, KY is $107/night.

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 September 22, 2026.

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

What are the best hotels in Winchester?

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

How many hotels are there in Winchester?

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.

Complete your trip to Winchester

Search HotelsCombined for deals to complete your trip to Winchester and save big.

Explore these cities in Kentucky

Looking to explore Kentucky during your trip? These are other popular cities nearby that HotelsCombined users visit

Visit Top Destinations

These destinations around the world are some of the most sought after locations from our users

Cities our users search for

Based on the last 12 months of user searches on HotelsCombined