Hotels in Winchester (Kentucky, USA)

How payments to us affect ranking

    • Popular choice

    Best Western Winchester Hotel

    3 Stars
    8.5Excellent (2,706 ratings)

    Exceptional hot breakfast spread, Seasonal outdoor swimming pool

    1.0 miles to City center
    from  $81
    See prices from 16 sites
    • Popular choice

    Baymont by Wyndham Winchester

    2 Stars
    6.8(931 ratings)

    Indoor pool with wood-paneled area, Rooms with ceiling fans

    1.1 miles to City center
    from  $49
    See prices from 20 sites

  3. Holiday Inn Express Lexington East - Winchester By Ihg

    3 Stars
    9.2Excellent (1,946 ratings)

    Indoor heated pool and fitness center, Exceptional hot buffet breakfast

    1.7 miles to City center
    from  $77
    See prices from 12 sites

  4. Hampton Inn Winchester

    3 Stars
    9.1Excellent (1,743 ratings)

    Pet-friendly accommodations, Seasonal outdoor swimming pool

    1.1 miles to City center
    from  $110
    See prices from 12 sites

  5. Comfort Inn Winchester

    2 Stars
    7.0(785 ratings)

    Heated indoor pool for year-round use, Vibrant bar with live entertainment

    1.6 miles to City center
    from  $70
    See prices from 12 sites
    • Popular choice

    Value Stay

    2 Stars
    6.9(340 ratings)

    Jacuzzi tub in select rooms, Renovated older property

    1.5 miles to City center
    from  $59
    See prices from 9 sites

  7. Red Roof Inn Winchester - Lexington East

    2 Stars
    6.5(688 ratings)

    Pet-friendly accommodations, 24-hour vending machines

    1.1 miles to City center
    Select dates to see exact prices

  8. College Park Getaway

    /No rating available 
    0.4 miles to City center
    Select dates to see exact prices

  9. 2-bedroom town-home in Winchester

    /No rating available 
    0.5 miles to City center
    Select dates to see exact prices

  10. The Winchester

    8.5Excellent (21 ratings)
    0.7 miles to City center
    Select dates to see exact prices

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

    9.9Excellent (24 ratings)
    2.2 miles to City center
    Select dates to see exact prices

  12. 4 Bed 3 Bath Clean , Spacious All Brick Home , Welcome Families And Work Groups

    9.7Excellent (22 ratings)
    0.6 miles to City center
    Select dates to see exact prices

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

    3 Stars
    8.6Excellent (5,241 ratings)

    Exceptional pet-friendly policy, Indoor pool for year-round enjoyment

    Lexington, 11.2 miles to Winchester
    from  $71
    See prices from 17 sites

  14. Econo Lodge Lexington Southeast

    2 Stars
    6.2(1,963 ratings)

    Pet-friendly stays for all sizes, Indoor pool for year-round enjoyment

    Lexington, 11.3 miles to Winchester
    from  $47
    See prices from 14 sites

  15. Days Inn Lexington SE Hamburg

    2 Stars
    6.8(2,382 ratings)

    Pet-friendly accommodations available, Essential business amenities

    Lexington, 11.3 miles to Winchester
    from  $43
    See prices from 16 sites

  16. Comfort Inn Lexington I-75

    2 Stars
    7.1(1,446 ratings)

    Child-friendly policies, Indoor heated swimming pool

    Lexington, 11.3 miles to Winchester
    from  $60
    See prices from 20 sites

  17. Hotel LEX, Trademark Collection by Wyndham

    3 Stars
    8.1Very good (2,048 ratings)

    Unique rustic-modern decor, Flexible event and meeting spaces

    Lexington, 11.4 miles to Winchester
    from  $80
    See prices from 7 sites

  18. Clarion Hotel Conference Center South

    3 Stars
    8.1Very good (1,268 ratings)

    On-site Barrel 53 restaurant and bar, Versatile event and meeting spaces

    Lexington, 11.4 miles to Winchester
    from  $59
    See prices from 4 sites

  19. Homewood Suites by Hilton Lexington-Hamburg

    3 Stars
    9.0Excellent (2,703 ratings)

    Pet-friendly accommodations available, Outdoor pool and picnic area

    Lexington, 12.4 miles to Winchester
    from  $104
    See prices from 12 sites

  20. 1840 Historic Antibellum Estate In The Heart Of The Bluegrass

    9.9Excellent (53 ratings)
    Paris, 6.8 miles to Winchester
    Select dates to see exact prices

  21. 1800’s Historical Log Cabin Near I-75 Interstatenn

    9.4Excellent (148 ratings)
    Lexington, 10.5 miles to Winchester
    from  $210
    See prices from 2 sites

  22. Edith Carriage House Getaway - I-75/hamburg

    8.8Excellent (16 ratings)
    Lexington, 10.6 miles to Winchester
    from  $119
    See prices from 2 sites

  23. Cabin In Kentucky Horse Country!

    9.9Excellent (165 ratings)
    Paris, 11.2 miles to Winchester
    Select dates to see exact prices

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

    9.8Excellent (12 ratings)
    Mount Sterling, 11.4 miles to Winchester
    Select dates to see exact prices

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

    9.5Excellent (10 ratings)
    Mount Sterling, 11.4 miles to Winchester
    Select dates to see exact prices

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

    9.8Excellent (18 ratings)
    Lexington, 11.5 miles to Winchester
    Select dates to see exact prices

  27. Family Lodgings Near Hamburg Shopping And Dining

    9.4Excellent (74 ratings)
    Lexington, 12.2 miles to Winchester
    Select dates to see exact prices

  28. Blue Heron

    /No rating available 
    Richmond, 11.1 miles to Winchester
    Select dates to see exact prices

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

    9.6Excellent (234 ratings)
    Lexington, 11.8 miles to Winchester
    from  $163
    See prices from 2 sites

  30. Rustic Mt Sterling Cabin2 Near Downtown Pets OK

    /No rating available 
    Mount Sterling, 11.4 miles to Winchester
    Select dates to see exact prices

  31. Rustic Mt Sterling Cabin1 Near Downtown Pets Ok

    /No rating available 
    Mount Sterling, 11.4 miles to Winchester
    Select dates to see exact prices

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

    /No rating available 
    Lexington, 11.9 miles to Winchester
    from  $544
    See prices from 2 sites

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

    9.1Excellent (15 ratings)
    Richmond, 11.4 miles to Winchester
    Select dates to see exact prices

  34. Charming 3-bedroom house in marvelous Mount Sterling with WiFi, AC

    /No rating available 
    Mount Sterling, 11.9 miles to Winchester
    Select dates to see exact prices

  35. Days Inn

    /No rating available 
    1.1 miles to City center
    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: January
    $105 per night
  • Yearly typical price
    $122 per night
  • Peak month: May
    $157 per night

Frequently Asked Questions about Winchester

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

    January is usually the cheapest month to book a hotel in Winchester, with typical prices around $105 per night based on 267 price comparisons.

  • When are hotel prices highest in Winchester?

    Hotel prices in Winchester are usually highest during May, with typical prices around $157 per night.

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

    Hotel prices in Winchester usually range from $93 per night to $164 per night, with typical prices around $122 per night.

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

    Hotel prices in Winchester are typically lowest in January at around $105 per night, rising to around $157 per night in May.

  • August

    2026

    $118
    $86 — $169

  • September

    2026

    $130
    $91 — $167

  • October

    2026

    $136
    $100 — $240

  • November

    2026

    $109
    $98 — $144

  • December

    2026

    $106
    $91 — $135

  • January

    2027

    $105
    $93 — $131

  • February

    2027

    $124
    $115 — $132

  • March

    2027

    $119
    $109 — $156

  • April

    2027

    $129
    $119 — $132

  • May

    2027

    $157
    $150 — $164

  • June

    2027

    Select dates to see exact prices

  • July

    2027

    Select dates to see exact prices

Frequently Asked Questions about Winchester

Hotels in Winchester

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