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An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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    Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

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    Our top choices for Winchester condo rentals

    1. Graffiti Art Haus - Walk to Central Bank Arena

    A bedroom with a bed, a nightstand, a lamp, and a large abstract mural on the wall.

    2. This condominium is a 1 bedroom(s), 1 bathrooms, located in Lexington, KY.

    A modern interior with a wooden accent wall, a glass table, and a bench.

    3. War Admiral @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown/GT College

    A wooden deck leading to a red door, brick walls, and a white door in the background.

    4. HUGE 3BR Penthouse King bed. Walk 2 RUPP elevator

    Interior

    5. The Luxe | Walk to Downtown|King Bed | 2BR Retreat

    An outdoor patio area with a fire pit, seating, and string lights against a sunset backdrop.

    6. Sir Barton @ The HoM- KY Horse Park 11min, Ark 30min, Walk Downtown / GT College

    A wooden deck leading to a red door, brick walls, and a white door in the background.

    7. Man O'War @ The HoM/KY Horse Park 11min/Ark 30min/Walk to Georgetown College

    A modern kitchen with dark cabinets, a coffee bar sign, stainless steel appliances, and a wooden floor.

    8. Secretariat @ The HoM- Ky Horse Park 11min, Ark 30min, Walk Downtown/GT College

    A two-story brick house with a front porch, a red door, and a well-maintained lawn.

    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.

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    Learn more about Winchester

    Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

    See all hotels in Winchester

    An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

    Top reviews in Winchester

    Holiday Inn Express Lexington East - Winchester by IHG

    A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

    Hampton Inn Winchester

    A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

    Home2 Suites Lexington Keeneland Airport, KY

    A hotel entrance with a covered walkway, a sign for 'Home 2 Suites by Hilton', and a parking area with cars.

    La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

    A rectangular indoor pool with a blue water surface, surrounded by a wooden deck and walls with a dark lower half.

    Home2 Suites By Hilton Richmond, Ky

    A modern bathroom with a toilet, a sink, a mirror, and a towel rack.

    Best Western Winchester Hotel

    A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

    Elwood Hotel & Suites

    An outdoor seating area with modern furniture, planters, and a building in the background.

    avid hotel Lexington - Hamburg Area by IHG

    A modern hotel lobby with seating areas, a reception desk, and a coffee machine.

    Holiday Inn Express Lexington - Horse Park Area by IHG

    A multi-story hotel with a curved entrance canopy, large windows, and a modern design.

    Home2 Suites by Hilton Lexington Hamburg

    An outdoor dining area with tables and chairs, string lights, and red umbrellas.

    Residence Inn by Marriott Lexington South/Hamburg Place

    A modern kitchen with a marble countertop, two pendant lights, and large windows offering a view of the street.

    Homewood Suites Lexington-Hamburg

    A modern kitchen with a stainless steel refrigerator, wooden cabinets, and a flat-screen TV mounted on the wall.

    TownePlace Suites by Marriott Lexington Keeneland/Airport

    An outdoor seating area with wicker furniture and a fire pit, adjacent to a building with large windows and a brick facade.

    Embassy Suites by Hilton Lexington Green

    A modern hotel lobby with a central seating area, a reception desk, and a high ceiling with natural light.

    Hampton Inn Richmond

    A modern room with a fireplace, two patterned armchairs, a small table, and a view of trees through large windows.

    Holiday Inn Express & Suites Lexington Midtown - I-75 by IHG

    A buffet area with multiple self-service stations for different food items.

    Frequently Asked Questions

    Why book your condo in Winchester with Expedia?

    Getting away shouldn't be difficult, so if you're on the lookout for condos at an affordable rate, Expedia has got your back. Keep costs down and select something small and affordable, or splurge on a luxury condo and spoil your favorite people. Our search filters make it a breeze to find a property in Winchester that matches your needs.

    How can I find cheap condos in Winchester?

    A great way to score cheap condos in Winchester is with Expedia's useful filter tool. Narrow down your search results by budget, amenities and star rating to snag unbeatable prices in just a few clicks.

    What is there to do in Winchester near my condo?

    Once you've settled into your hotel, venture out and discover the fantastic things Winchester has on offer. Southwind Golf Course is a top attraction to add to your travel itinerary.

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