Bed & Breakfast Guides and Directories

• BedandBreakfast.com
  is a leading directory of bed and breakfasts, inns, and boutique lodgings throughout Winchester and neighboring Kentucky towns. Shop, compare, and book from their large selection of Winchester B&B properties with many exclusive deals offered. Gift certificates are also available. BedandBreakfast.com has nearly 7,000 property listings throughout the United States with 50,000 reviews, 80,000 property photos, and interactive maps.

Cabins & Cottages

• Scenic Cabin Rentals
  513-683-1552
  Perfect get-a-way trip for couples, families and friends who love nature and enjoy the nearby outdoors. There are 12 wonderful cabins for you to enjoy. After a day of hiking or riding enjoy grilling out and having a campfire outside or romantic fire inside. To top it off, soak in the Jacuzzi tub or hot tub. more...

Condos & Vacation Rentals

• Winchester, KY,Vacation Rentals By Owner on VRBO®
  Renting a private vacation home offers the affordability, exceptional value, and personal attention that you deserve. Most private vacation homes offer considerably more space than you will find in the typical hotel room often at a reduced cost. Now, families can vacation together and still have room to breathe. View their list of vacation rentals now...

• HomeAway Vacation Rentals in Winchester, KY
  Forget ordinary hotel rooms! Finding the perfect vacation getaway in Winchester, KY is easy on HomeAway.com. Choose from 75,000 homes, condos, guesthouses, cottages, and cabins worldwide, and inquire directly with property owners through the site. HomeAway.com vacation rentals offer a unique local experience, often less expensive and more spacious than hotel rooms.

• Rentalo.com
  saves you time! Click to inquire & compare offers from Vacation Rentals, Hotels, and Bed & Breakfasts in Winchester, KY. Find the best deals on short term accommodations using this award-winning, traveler-tested website. Browse our extensive inventory offering leisure and business travelers a wide variety of lodging options; from a budget studio to a luxury villa on a private island, from a small boutique hotel or bed and breakfast to a 5 star resort. Find the perfect place to stay for every occasion including family vacations, romantic getaways, business trips, ski, beach or golf vacations.

• Winchester, KY, Vacation Rentals on Vacation Rentals.com
  Are you still making hotel reservations? At VacationRentals.com, customize your next vacation and take advantage of off-season discounts, last minute deals, and freebies! No matter what destination or property type or number of bedrooms you’re looking for, you can find an affordable vacation rental that will suit the needs of you and your fellow travelers. So, what are you waiting for? No matter how tight your budget, you can book your dream vacation on VacationRentals.com today!

Motels/Hotels

• Best Western Country Squire
  1307 West Lexington Avenue • Winchester, KY 40391
  606-744-7210
  The Best Western Country Squire is a hotel where one can experience the true meaning of Southern hospitality. The renovated guest rooms are not only clean and comfortable but furnished with a microwave, fridge, in-room coffee/tea maker, iron, ironing board and hairdryer.   map

• Days Inn
  1100 Interstate Drive • Winchester, KY 40391
  859-744-9111
  The Days Inn has over 60 rooms and offers a number of amenities, such as a continental breakfast, an outdoor pool, a restaurant, a lounge, and a meeting room.  map

• Hampton Inn
  1025 Early Drive • Winchester, KY 40391
  Downtown
  859-745-2000, 800-426-7866
  Hampton Inn features 59 rooms, high-speed internet access and ergonomic desk chairs in the guest rooms, a state-of the-art fitness center ,outdoor pool, meeting rooms and a breakfast buffet  more...  map

• Holiday Inn Express
  5250 Revilo Road • Winchester, KY 40391
  859-745-3009, 800-HOLIDAY
  Restaurants are adjacent to the property and a mall is adjacent to the hotel. The hotel has 58 rooms, interior corridor with elevator, indoor heated pool, fitness center, and deluxe continental breakfast. Minutes from Bluegrass Airport, University of Kentucky, Keeneland Race Track, Kentucky Horse Park, Deer Run Stables, Lexmark International, Toyota, Shaker Village, and the Bluegrass Heritage Museum.   map

• Quality Inn & Suites
  960 Interstate Drive • Winchester, KY 40391
  859-737-3990
  Offers 47 luxury suites and has many amenities, including continental breakfast, an indoor pool, a meeting room, and wireless Internet service. A variety of restaurants and cocktail lounges are located in the surrounding area.   map