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Winchester hotels

Wed 26/6
Thu 27/6

Search hundreds of travel sites at once for hotels in Winchester, Kentucky

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Best Winchester hotels

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Most recommended Winchester hotels

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Best Western Winchester Hotel - Winchester - Building
Best Western Winchester Hotel
8.1 Very Good
R2 152+
R2 152+
Parking
Free Wi-Fi
Pool
Pet-friendly
Red Roof Inn Winchester - Winchester - Building
R1 295+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
Hampton Inn Winchester
8.9 Very Good
R2 888+
R2 888+
Parking
Free Wi-Fi
Pool
Pet-friendly
Comfort Inn
5.3 Fair
R1 673+
R1 673+
Parking
Free Wi-Fi
Pool
Air conditioning
R1 862+
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 583+
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
Best Western Winchester Hotel
8.1 Very Good
R2 152+
R2 152+
Parking
Free Wi-Fi
Pool
Pet-friendly
Hampton Inn Winchester
8.9 Very Good
R2 888+
R2 888+
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 295+
Parking
Free Wi-Fi
Pet-friendly
Air conditioning

How much is a Winchester hotel?

Here are our most popular & best value hotels

2 stars and below

Good to know

Low season

February

High season

October

Average price (weeknight)

R2 017

Average price (weekend night)

R2 216
Cheapest month to stay with an average 14% drop in price.
Most expensive month to stay with an average 45% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a hotel in Winchester

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Winchester hotel deals

  • If you’re looking for a cheap hotel in Winchester, you should consider visiting during the low season. You'll find cheaper accommodations in Winchester in February and January.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Winchester if you stay on a Tuesday. The opposite is true for, Wednesday, which is usually the most expensive day.
  • Fitness enthusiasts traveling to Winchester should look forward to their stay at either Holiday inn Express Lexington or Holiday Inn Express & Suites Mt Sterling North. Both hotels are operated by the IHG group and provide state of the art fitness facilities that include modern equipment such as elliptical machines, free weights, and treadmills.
  • If you’re looking to stay at an environmentally conscious hotel while on your visit to Winchester, consider booking your reservation at either the Hampton Inn Winchester or Comfort Inn & Suites. Both hotels have multiple programs aimed towards environmental sustainability including water conservation, energy efficiency, and waste reduction.
  • If you’re looking for the most convenient dining options during your stay in Winchester, consider booking your hotel reservation at either Hampton Inn Winchester or Ramada Limited Mount Sterling. Both hotels have onsite restaurants and offer free minimal breakfast, as well as an optional breakfast buffet. In addition, Hampton Inn also has an onsite bar.
  • Guests traveling to Winchester for longer term stays should consider staying at either the Red Roof Inn Lexington or Best Western Winchester Hotel. Both hotels offer a variety of services perfect for extended stays such as daily housekeeping, as well as self-service laundry and wake-up calls at the Red Roof Inn.
  • If you would want to work on your golf swing while on your visit to Winchester, book your stay at Ramada Limited Mount Sterling, Baymont by Wyndham Winchester, or the Comfort Inn. All three of these hotels have access to some of the finest golf courses around Winchester.

FAQs when booking a hotel in Winchester

  • Where is best to stay in Winchester when traveling on business?

    Business travelers to Winchester are bound to enjoy their hotel experience at either the Red Roof Inn Lexington or Hampton Inn Winchester. Both hotels provide a variety of business facilities, including a well-equipped business center and several meeting rooms that can be fitted with audiovisual equipment upon the guest’s request.

  • Which hotels in Winchester are family-friendly?

    If you’re traveling to Winchester accompanied by your family, consider staying at either the Days Inn by Wyndham Mt. Sterling or Best Western Winchester. Both hotels have room offerings that cater towards larger families by including living areas, kitchenettes, and sofa beds. Additionally, the Days Inn allows children under 17 to stay at the hotel free of charge, while the Best Western allows children under 12 to stay at no charge if staying with an adult.

  • Which hotels in Winchester offer accessibility services?

    If you will be in the need of accessibility services while in Winchester, consider making your hotel reservation at the Holiday Inn Express & Suites Lexington East or Comfort Inn & Suites. Both hotels offer multiple accessibility services that include an accessible pool and accessible parking. The hotels also have helpful staff who are ready to offer any additional assistance upon request.

  • Which hotels in Winchester are pet-friendly?

    If you’re traveling with your furry friend, consider booking your hotel stay at the Red Roof Inn Winchester or Baymont by Wyndham Winchester. Red Roof Inn accommodates one pet at no additional fee, and has no maximum weight limit. Baymont by Wyndham only allows guests to bring along one dog at an additional fee, but has no weight limit. Both hotels have grassy pet relief areas on the hotel premises.

  • How do I find a hotel in central Winchester?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, which allows you to pick the central Winchester districts. You can also do a search using the city map to choose a specific location, like Winchester city centre

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

  • Are there Winchester hotels with free parking?

    There are many hotels in Winchester that offer both parking and free parking. Popular choices among KAYAK users include Best Western Winchester Hotel, Red Roof Inn Winchester and Hampton Inn Winchester.

Where to stay in Winchester?

Our map will help you find the perfect place to stay in Winchester by showing you the exact location of each hotel.