Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.

Midway, Kentucky
$207 avg/night
Minimum Stay 2 Nights
Bed 2

Bed

Bath 1

Bath

Home Private Vacation Home

Property Type

Sleep 4

Max Sleeps

Night 2 nights

Min Stay

This unique, early 1800’s historic house sits 50 FEET from the railroad. The train blows by 3x during the day, tooting & whistling away & once or twice at night. It is the second oldest residence built in Midway. The plot of land where the house sits was one of the initial purchases from the railroad company which was one the first towns in KY to build a Railroad Town. GUESTS NEED TO CONFIRM THEY CAN HANDLE THE ORIGINAL OLD STEEP & NARROW STAIRCASE BEFORE BOOKING ACCEPTED.
Guests will enjoy their private, bright & cozy upstairs with 2 nicely sized bedrooms with plenty of closet space. The bathroom in between the bedrooms & breakfast nook is very small, but clean & efficient. There is a mini fridge, coffee & tea station. Ice bucket @ 5:00 pm each night is available upon request. Entrance & exit is through the front door & through the one-room art gallery which is closed off from the rest of the house. 9 ORIGINAL VERY STEEP & NARROW STAIRS leads to the cheery upstairs accommodations. STAIRS ARE NOT FOR PEOPLE WITH MOBILITY ISSUES. BIG, HEAVY SUITCASES ALSO WILL POSE A PROBLEM IF YOU ARE NOT UP FOR WRANGLING THEM UP THE 9 STAIR CLIMB. GUESTS MUST ACKNOWLEDGE THEY HAVE SEEN/READ RE. STAIRS BEFORE BOOKING IS ACCEPTED Please see pictures :)
Ample off street parking is available. If you are bicycle-touring/racing, garage arrangements in back can be be made for bicycles. Off street horse trailer parking can also be arranged.
Ellen, the host, lives in the back part of the house which is closed off from the art gallery room & upstairs. The house is located on the residential side of Main St. (aka Railroad St.) & is 1/2 block away from restaurants & shops.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Property Does Not Allow Children
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Electric Kettle Refrigerator
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Garden
  • BATHROOMS

    1 Bathroom Hair Dryer Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Cycling Nearby Fishing Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Horse Riding Nearby Power Boating Nearby Winery Tours Nearby
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In The City Center
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Limited Housekeeping
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 02:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Availability

Review Review

  • Susan

    Submitted May 3, 2022

    Stayed Apr 29, 2022

    The house and yard were adorable. Ellen was a gracious hostess and very good with communication. The downtown was wonderful with good restaurants and walkable from the house. We really enjoyed our stay.

  • Submitted Jul 22, 2021

    Stayed Jul 18, 2021

    Highly recommend this unique accommodation tucked away in the center of downtown Midway.

  • Submitted Apr 12, 2021

    Stayed Apr 8, 2021

    Great place to go and get away from everything. Midway is a charming small town. Loved the limited technology, just what you bring, it’s a great way to live. Ms Skidmore’s house was charming and elegant. Her artwork is a very nice touch throughout. Highly recommended.

  • John T.

    Submitted May 24, 2026

    Stayed May 19, 2026

    Noting but character and charm in this historic house in the beautiful town of Midway, KY. This is the epitome of a Bluegrass experience. When you visit, don't fail to eat and Heirloom, just down the street.

  • ALISHA P.

    Submitted May 4, 2026

    Stayed Apr 30, 2026

    We thoroughly enjoyed our stay! Ellen is an excellent host and accommodated our every request with gladness. The atmosphere and decor of this lovely home takes one back to another time in old Midway. It’s walkable to all of the best dining and shopping in downtown Midway. The staircase does have steep stairs, and some may find the shower a little small, but neither were issues for us. The rooms were comfortable. We were provided a small fridge, single cup coffee maker and tea kettle with great tea and coffee selections. There were so many cute touches. We will be returning for sure.

  • Submitted Apr 30, 2026

    Stayed Apr 22, 2026

    I loved being in this cozy, historic home. So refreshing being somewhere with history and personality. Ellen is an absolute joy, and being surrounded with her artwork made me smile every day. The beds are comfy, the little coffee nook and mini fridge is such a nice, hospitable touch. The location is perfectly centered between Keeneland and The Horse Park. Also, easy to get to Buffalo Trace for those bourbon lovers. Downtown Midway had a surprising number of resteaunts to choose from in walking distance. And do NOT miss going to your host's charming art gallery before dinner. Absolute gem.

  • wendy R.

    Submitted Apr 28, 2026

    Stayed Apr 10, 2026

    We love, love, love staying here! It’s beautiful, comfortable and just steps from everything in Midway. We love staying here! Ellen is very gracious accommodating. Can’t wait to stay here again.

  • Tylor T.

    Submitted Oct 29, 2025

    Stayed Oct 24, 2025

    Very historic place, accommodating host

  • Janine S.

    Submitted Oct 19, 2025

    Stayed Oct 17, 2025

    Ellen is lovely and welcoming. The space was perfect and just as described. We truly enjoyed our visit to this quaint town.

  • Julia C.

    Submitted Oct 18, 2025

    Stayed Oct 4, 2025

    Second time staying at this home. Wonderful character and a wonderful host. The train is something to be aware of but in my mind adds to the charm.

  • jessica b.

    Submitted Jun 8, 2025

    Stayed Jun 6, 2025

    Midway is such a rare jewel!The Railway Guesthouse felt like home from the time we arrived! Ellen is an amazing person , so lovely inside and out!!! We can’t wait to come back “home”

  • john k.

    Submitted Jun 7, 2025

    Stayed May 21, 2025

    Great location

  • Misty H.

    Submitted Jun 3, 2025

    Stayed May 30, 2025

    We stayed here for the recent Railbird festival. It was clean, cute and good for our needs of this trip since we were not going to be there for meals and things.

  • Owen R.

    Submitted May 2, 2025

    Stayed Apr 14, 2025

    Conviently located and cozy.

  • John T.

    Submitted Dec 15, 2024

    Stayed Dec 10, 2024

    Beautiful historic house in a village setting. Surrounded by the best of the bluegrass.

  • David C.

    Submitted Oct 26, 2024

    Stayed Oct 24, 2024

    What a quaint and lovely home! Well preserved 200 year old home with beautiful artwork to enjoy. Great location for Keeneland, UK activity and bourbon trail!! Ellen was a great hostess!!

  • wendy R.

    Submitted Oct 17, 2024

    Stayed Oct 4, 2024

    This is such a beautiful historic home. Location couldn’t have been better for our days at Keeneland since we could go in the pretty back roads and miss the huge traffic jams. At night, we booked dinner in some fabulous small restaurants in Midway, which were just a few steps away. The home was comfortable and yes, the stairs are steep, but no problem for us. Would absolutely stay here again!

  • Elizabeth V.

    Submitted Sep 25, 2024

    Stayed Sep 18, 2024

    Host is awesome-- would love to come back!

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Total

Includes taxes and fees
$207+
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