Hotels in Winchester (Kentucky, USA)

How payments to us affect ranking

35 hotels in Winchester

  1. Baymont by Wyndham Winchester

    2 Stars
    Indoor pool and fitness center
    See prices from 13 sites
    from$97

  2. Best Western Winchester Hotel

    3 Stars
    Outdoor pool for seasonal recreation
    See prices from 15 sites
    from$108

  3. Holiday Inn Express Lexington East - Winchester By Ihg

    3 Stars
    On-site fitness and pool
    See prices from 11 sites
    from$124

  4. Hampton Inn Winchester

    3 Stars
    Banquet facilities for large groups
    See prices from 11 sites
    from$176

  5. Comfort Inn Winchester

    3 Stars
    On-site fitness center for guests
    See prices from 13 sites
    from$66

  6. Value Stay

    2 Stars
    Select rooms with jacuzzi tubs
    See prices from 8 sites
    from$71

  7. College Park Bungalow

    Select dates to see exact prices

  8. 2-bedroom town-home in Winchester

    Select dates to see exact prices

  9. 4 Bed 3 Bath Clean , Spacious All Brick Home , Welcome Families And Work Groups

    Select dates to see exact prices

  10. Charming 3-bedroom House With Pool, Wifi, Ac In Tranquil Winchester

    Select dates to see exact prices

  11. Aisling House - Historic Hospitality

    Select dates to see exact prices

  12. The Winchester

    Select dates to see exact prices

  13. Red Roof Inn Lexington - Winchester

    2 Stars
    Proximity to Interstate 64
    Select dates to see exact prices

  14. La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

    3 Stars
    Indoor pool and fitness center
    See prices from 14 sites
    from$107

  15. Econo Lodge Lexington Southeast

    2 Stars
    Swim in on-site indoor pool
    See prices from 15 sites
    from$69

  16. Hotel LEX, Trademark Collection by Wyndham

    3 Stars
    Large Indoor Pool And Arcade
    See prices from 5 sites
    from$95

  17. Days Inn by Wyndham Lexington Southeast

    2 Stars
    On-site fitness center access
    See prices from 14 sites
    from$63

  18. Comfort Inn Lexington I-75

    3 Stars
    Indoor heated swimming pool access
    See prices from 15 sites
    from$86

  19. Clarion Hotel Conference Center South

    3 Stars
    On-site Barrel 53 restaurant dining
    See prices from 8 sites
    from$94

  20. Homewood Suites by Hilton Lexington-Hamburg

    3 Stars
    Maintain fitness in on-site gym
    See prices from 11 sites
    from$120

  21. 1840 Historic Antibellum Estate In The Heart Of The Bluegrass

    Select dates to see exact prices

  22. 1800’s Historical Log Cabin Near I-75 Interstatenn

    Select dates to see exact prices

  23. Cabin In Kentucky Horse Country!

    Select dates to see exact prices

  24. Rustic Mt. Sterling Cabin 1 Near Downtown • Pets Ok

    Select dates to see exact prices

  25. Rustic Mt. Sterling Cabin 2 Near Downtown • Pets Ok

    Select dates to see exact prices

  26. Equine Escape - Newly Updated, Close To Interstate, Hospitals

    Select dates to see exact prices

  27. Blue Heron

    Select dates to see exact prices

  28. Get back to Nature. Close to Lexington, Relax & Revitalize

    Select dates to see exact prices

  29. Unique Stay In A 1907 Log Cabin On The Kentucky River

    Select dates to see exact prices

  30. Rustic Mt Sterling Cabin2 Near Downtown Pets OK

    Select dates to see exact prices

  31. Rustic Mt Sterling Cabin1 Near Downtown Pets OK

    Select dates to see exact prices

  32. Charming 3-bedroom Detached Cottage On Horse Farm Near Lexington And Georgetown.

    Select dates to see exact prices

  33. Fully Furnished 4BR Home in Lexington Short & Mid-Term

    Select dates to see exact prices

  34. The Guesthouse At Rosecrest Farm

    Select dates to see exact prices

  35. Curated 4BD/3.5BA Ranch, Hamburg Off I-75 & 14 Min to KY Horse Park Pet-Friendly

    Select dates to see exact prices

The prices and availability we receive from booking sites change constantly. This means you may not always find the exact same offer you saw on trivago when you land on the booking site.

Other stays in Winchester

Popular hotel categories in Winchester

When to book a hotel in Winchester

  • Cheapest month: December
    $133 per night
  • Yearly typical price
    $148 per night
  • Peak month: May
    $166 per night

Frequently Asked Questions about Winchester

  • When is the cheapest time to book a hotel in Winchester?

    December is usually the cheapest month to book a hotel in Winchester, with typical prices around $133 per night based on 2,276 price comparisons.

  • When are hotel prices highest in Winchester?

    Hotel prices in Winchester are usually highest during May, with typical prices around $166 per night.

  • How much does a hotel in Winchester cost per night?

    Hotel prices in Winchester usually range from $113 per night to $179 per night, with typical prices around $148 per night.

  • How do hotel prices in Winchester change throughout the year?

    Hotel prices in Winchester are typically lowest in December at around $133 per night, rising to around $166 per night in May.

  • November

    2026

    $142
    $121 — $216

  • December

    2026

    $133
    $113 — $194

  • January

    2027

    $157
    $133 — $196

  • February

    2027

    $144
    $140 — $167

  • March

    2027

    $157
    $143 — $182

  • April

    2027

    $148
    $135 — $167

  • May

    2027

    $166
    $160 — $179

  • June

    2027

    Select dates to see exact prices

  • July

    2027

    Select dates to see exact prices

  • August

    2027

    Select dates to see exact prices

  • September

    2027

    Select dates to see exact prices

  • October

    2027

    Select dates to see exact prices

Frequently Asked Questions about Winchester

Hotels in Winchester

These hotels may also be interesting for you...

Points of Interest - Winchester

Top Destinations

More Top Destinations

See all stays in Winchester