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

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

Built in early 1800,s
Entrance/Parlor
Parlor & way to upstairs
To upstairs
Original steep & narrow staircase. Guests must OK this before booking accepted.

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Midway, KY
  • Place, Equus Run Vineyard & Winery
    ‪4 min drive‬
  • Place, Old Friends Thouroughbred Retirement Farm
    ‪8 min drive‬
  • Place, Kearney Hills Golf Links
    ‪10 min drive‬
  • Airport, Lexington, KY (LEX-Blue Grass)
    ‪22 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Clover Room

1 Double Bed

Poppy Room

1 Queen Bed

1 bathroom

Little Blue

Toilet · Shower only

Spaces

Garden

About this property

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

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 where you will also find Ellen’s Art Gallery & Gift Shop THROW ME A CARROT. She can be reached anytime if needed on her cell phone (preferably by text) during your stay. Guests receive 15% discount at THROW ME A CARROT :)

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House Rules

Check in after 12:00 PM

Minimum age to rent: 21

Check out before 12:00 PM

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Children

Adults only

CHILDREN FROM 9 YRS IS PREFECT FOR THE PROPERTY

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Events

No events allowed

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Pets

No pets allowed

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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:

Remove personal items, remove leftover food and drinks and take out the rubbish

Turn off the lights, lock the doors and return the keys

Please leave your key on the little captain’s desk next to the front door as you leave :)

Trash cans are in the back of the driveway which is easy to see. One for reg. and one for recycling.

Failure to complete these may result in a negative review from the host.

Please place used dishes etc. in basket. If you’d like clean dishes and refreshed ice-bucket, please leave at top of stairs when leaving for the day.

Please park in house’s off-street driveway to right of house leaving space for another car to your side not in front of the house

Important information

You need to know

Property # 2001607vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Midway

Located in Midway, this holiday home is in the city centre. Buffalo Trace Distillery and Equus Run Vineyard & Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Cove Spring Park and Buckley Wildlife Sanctuary & Audobon Center. Old Friends Thouroughbred Retirement Farm and Blue Grass Railroad Museum are also worth visiting. Discover the area's water adventures with power boating and fishing nearby, or enjoy the great outdoors with cycling and hiking.
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Map
Midway, KY

What's nearby

  • Equus Run Vineyard & Winery - 4 min drive - 7.2 km
  • Old Friends Thouroughbred Retirement Farm - 8 min drive - 14.6 km
  • Kearney Hills Golf Links - 10 min drive - 20.5 km
  • Masterson Station Park - 12 min drive - 16.9 km
  • Kentucky Horse Park - 15 min drive - 29.3 km

Getting around

  • Lexington, KY (LEX-Blue Grass) - 22 min drive

Restaurants

  • ‪McDonald's - ‬17 min walk
  • ‪Rocky’s Pub - ‬11 min drive
  • ‪Wallace Station Deli and Bakery - ‬4 min drive
  • ‪The Midway Bakery - ‬14 min walk
  • ‪Don Jockey - ‬2 min walk

Frequently asked questions

Is Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.?

As of 13 May, 2026, prices found for a 1-night stay for 2 adults at Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland. on 20 Sept, 2026 start from S$279, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.?

On-site parking is available at the property.

What time is check-in at Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.?

Check-in begins at 12:00 PM.

What time is check-out at Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.?

Checkout is at 12:00 PM.

Where is Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland. located?

Located in the heart of Midway, this holiday home is 3.8 mi (6 km) from Equus Run Vineyard & Winery and within 12 miles (20 km) of Kentucky Horse Park and Old Friends Thouroughbred Retirement Farm. Headley-Whitney Museum and Nostalgia Station Toy Train Museum are also within 9 miles (15 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 42 out of 50 reviews
Rating 8 - Good. 8 out of 50 reviews
Rating 6 - Okay. 0 out of 50 reviews
Rating 4 - Poor. 0 out of 50 reviews
Rating 2 - Terrible. 0 out of 50 reviews

10/10

Cleanliness

9.0/10

Amenities

9.4/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

8/10 Good

Tylor T.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy
Very historic place, accommodating host
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

ALISHA P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Janine S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ellen is lovely and welcoming. The space was perfect and just as described. We truly enjoyed our visit to this quaint town.
Stayed 2 nights in Oct 2025
Verified

8/10 Good

john k.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midway stay

Great location
Stayed 6 nights in May 2025
Verified

10/10 Excellent

Julia C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 19 Oct, 2025
Lovely seeing you & yours ;)
Verified

10/10 Excellent

Elizabeth V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Host! Convenient location!

Host is awesome-- would love to come back!
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Sarah R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Adorable home in the heart of a cute small and historic town

We had a wonderful stay. The house was so cute and comfortable. Very affordable and we will definitely be staying again.
Stayed 2 nights in Sep 2022
Response from VrboOwner on 22 Sept, 2022
Thank you Sarah! Look forward to having you again!
Verified

10/10 Excellent

Misty H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute and efficient

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.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Anna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great and will stay again

Perfect for a short trip. I believe it'd be perfect for a long trip too.
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Julia C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay in a charming place

We thoroughly enjoyed our stay at this charming and unique place. We loved the original features of the house, and the location was perfect for walking to restaurants and shops. Ellen is a wonderful host and artist and our stay at the house made our trip extra enjoyable.
Stayed 3 nights in May 2022
Response from VrboOwner on 2 Jun, 2022
Lovely guests!!! Enjoyed having cyclists stay with me doing the Horsey 100 :)))
Verified

10/10 Excellent

jessica b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midway friends get away

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”
Stayed 2 nights in Jun 2025
Response from VrboOwner on 8 Jun, 2025
You were delightful guests!!! Thank you so much, Jessica. Look forward to seeing you again.
Verified

8/10 Good

Owen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midway 2025

Conviently located and cozy.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

John T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A taste of Kentucky

Beautiful historic house in a village setting. Surrounded by the best of the bluegrass.
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

Chris P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming Property and Awesome Stay

We booked this property the weekend of the derby. It was perfect for us. Everything is well thought of- and just absolutely charming. Property owner is accessible and wonderful to communicate with- we will definitely rebook in the future ❤️
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Sunny M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

70th Birthday

Brought our mom to midway to celebrate her 70th birthday. Our stay was amazing. Ellen is the best!! The place was just perfect!
Stayed 1 night in Dec 2022
Response from VrboOwner on 20 Dec, 2022
It was a joy having you!!! You were my first guests to have around the holiday. Thank you for staying with me and being so fun & festive.
Verified

10/10 Excellent

David C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Midway gem!

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!!
Stayed 2 nights in Oct 2024
Response from VrboOwner on 27 Oct, 2024
Thank you for staying here! You were lovely guests to host :)
Verified

10/10 Excellent

Kevin H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint and cozy accommodations

Ellen was a wonderful She was very knowledgeable about the area and gave us many fantastic recommendations for activities and eateries. The accommodation were as stated on the site. Lovely!
Stayed 2 nights in Mar 2023
Verified

8/10 Good

Jeff M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great character

Home built in early 1830s in a nice / quiet town. Very clean and comfortable. Ellen was a wonderful host.
Stayed 2 nights in Sep 2021
Response from VrboOwner on 28 Sept, 2021
Dear Mr. McMillan, Is there anything I can do to make the 4* rating you scored my place a 5*? That was my first one, so would like your input to make improvements. Many thanks, Ellen.
Verified

10/10 Excellent

wendy R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Historic Home Right in Midway

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!
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Susan J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique and lovely…. Very personal experience.

A new experience for us…nothing else like it! Wonderfully novel!
Stayed 2 nights in Mar 2023
Verified

8/10 Good

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming Midway

We were in town for the Land Rover three day event. Midway was charming and the people were unbelievably friendly! Ellen was awesome. Her home was comfortable with delightful furnishings and really added to our experience.
Stayed 3 nights in Apr 2023
Verified

10/10 Excellent

Megan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved LOVED Loved it!

Beautiful home, perfectly and accurately described. Ellen was a great host. Her art is inspirational. The small town of Midway was a breath of fresh air from the city. Everyone we encountered was gracious and polite. We can't wait to visit again.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 22 Jun, 2023
What a wonderful review. Thank you! You all were delightful.
Verified

10/10 Excellent

Connie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

In town for the Thoroughbred Makeover at the Kentucky Horse Park.

My stay couldn’t have been more perfect! The horse park is a short drive and several excellent restaurants are within walking distance. The town of Midway and the accommodations were absolutely charming. Ellen’s beautiful artwork, fascinating life story and love of horses (as evidenced in her art) made my stay even more memorable and special. I would definitely recommend a stay here. Ellen, thank you so much for a fabulous stay.
Stayed 5 nights in Oct 2022
Response from VrboOwner on 21 Oct, 2022
Connie, it was really, really fun seeing your beautiful mare IRENE win the Freestyle division at the RRP! Congratulations! Thank you for staying with me and I hope to see you again! Happy Trails, Ellen.
Verified

10/10 Excellent

Holly W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just what we needed.

This is our 3rd stay with Ellen for a well needed girl’s weekend. As always, we left with more great memories. Ellen is a very attentive host and we love the convenience of being able to walk to the dinner on Main St. Having coffee in the morning was very cozy. That’s all we needed! Thanks Ellen, We’ll be back.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 26 Apr, 2023
You all are lovely guests!!! Look very much forward to seeing you again. Thank you so much Holly.
Verified

8/10 Good

Wanda V.

Liked: Cleanliness, communication, location

Keeneland Outing

Quaint & enjoyable for those who can navigate steep stairs & cute, tiny bathroom. Two spacious bedrooms; we created a cozy sitting area in the larger room. Train lovers will enjoy close proximity to the tracks and the romantic sounds of it passing through the sweet town, which has wonderful shops and dining options. The owner is an accomplished artist with her studio and gallery on the first floor.
Stayed 3 nights in Oct 2021
Response from VrboOwner on 19 May, 2022
Steep, narrow stairs are strongly emphasized in property description & photos. Small bathroom also described & photographed accurately, but more pictures will added.

About the host

Hosted by Ellen Skidmore

Host profile image

Ellen found Midway in 2020 & loves living & working here. Her gallery/studio/gift shop is a block away on East Main St. She enjoys spending time with her dogs in the backyard & her horse which she boards at a farm nearby,

Why they chose this property

Perfect for people who appreciate historic homes. This house was built in the early 1800’s. It is located on the residential side of Main St. but Is only a short block’s walk to the Railroad Shops & restaurants of Midway.
Midway is just off interstate 64 so only15 minutes to the Kentucky Horse Park, Keeneland Race Course & the infamous Bourbon Trail, horse farm tours, etc.
BEFORE RESERVATIONS ARE ACCEPTED, GUESTS MUST ACKNOWLEDGE THEY HAVE SEEN THE 9 STEEP/NARROW STAIRS PHOTO/DESCRIPTION,

What makes this property unique

Desk, WiFi, great beds, reading/relaxing chairs, big closets. The Cookie Nook which is in between the two bedrooms and opposite the bathroom has a Keurig coffee maker, electric water kettle, mini fridge with sugar, cream, plates etc. provided.
Ellen lives on the property works a block away in her studio/gallery/gift shop and is usually around answer any questions preferably by text. GUESTS MUST ACKNOWLEDGE THEY HAVE SEEN/READ 9 STEEP/NARROW STAIRS DESCRIPTION BEFORE RESERVATION IS ACCEPTED.

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