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2nd Story Historic Downtown 2BR with Modern Amenities

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Fridge, microwave, oven, stovetop
Onsite parking
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Exterior
Onsite parking

Reviews

9.0 out of 10
Wonderful

Entire apartment

2 bedrooms1 bathroomSleeps 5

Popular amenities

  • Kitchen
  • Parking available
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

Map
Winchester, KY
  • Bluegrass Heritage Museum
    ‪6 min walk‬
  • Clark Regional Medical Center
    ‪2 min drive‬
  • Lykins Park
    ‪4 min drive‬
  • Lexington, KY (LEX-Blue Grass)
    ‪31 min drive‬

Room options

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About the neighborhood

Winchester

City center stay.You'll find Bluegrass Heritage Museum and College Park within a 15-minute walk of this Winchester apartment. Clark County Public Library and GRCHS Baseball Field are also within 2 miles (3 km).
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What's nearby

  • Bluegrass Heritage Museum - 5 min walk - 0.3 miles
  • Clark Regional Medical Center - 2 min drive - 1.4 miles
  • Lykins Park - 4 min drive - 2.0 miles
  • Fort Boonesborough State Park - 16 min drive - 10.1 miles
  • University of Kentucky - 29 min drive - 22.9 miles

Getting around

  • Blue Grass Airport (LEX) - 31 min drive

Restaurants

  • ‪Taco Bell - ‬3 min drive
  • ‪Popeyes Louisiana Kitchen - ‬4 min drive
  • ‪Dairy Queen - ‬5 min walk
  • ‪Fazoli's - ‬4 min drive
  • ‪Rally's - ‬3 min drive

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

2nd Story Historic Downtown 2BR with Modern Amenities

Experience this unique and historic two bedroom apartment in the heart of downtown Winchester Kentucky. This building is over 150 years old and rich in history in the community, however, features modern amenities to ensure an amazing stay. This building is immediately across the street from the historic clocktower courthouse.

You'll feel right at home in the fully remodeled bathroom (European Wet Room), kitchen and bedrooms. You'll also feel plenty of old world charm. Walking distance to all!

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Total includes taxes and fees
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Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • In the mountains
  • On a lake

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 1:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: We love our animal guests.

Children and extra beds

  • Children are welcome.
  • Note from host: All ages welcome.

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

2nd Story Historic Downtown 2BR With Modern Amenities Apartment
2nd Story Historic Downtown 2BR With Modern Amenities Winchester

Frequently asked questions

How close is 2nd Story Historic Downtown 2BR with Modern Amenities to the airport?

This apartment is 27.2 mi (31-min drive) away from the Blue Grass Airport (LEX) airport, the closest popular airport to the property.

How much does it cost to stay at 2nd Story Historic Downtown 2BR with Modern Amenities?

As of May 9, 2025, prices found for a 1-night stay for 2 adults at 2nd Story Historic Downtown 2BR with Modern Amenities on May 19, 2025 start from $98.0, excluding 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.

Does 2nd Story Historic Downtown 2BR with Modern Amenities have an airport shuttle?

Airport shuttle services are not available at this apartment.

Does 2nd Story Historic Downtown 2BR with Modern Amenities offer free breakfast?

This apartment does not offer free breakfast.

Is there a casino at 2nd Story Historic Downtown 2BR with Modern Amenities?

No, there is no casino at this apartment.

What time is check-in at 2nd Story Historic Downtown 2BR with Modern Amenities?

Check-in begins at 1:00 PM.

Is there free parking at 2nd Story Historic Downtown 2BR with Modern Amenities?

Free parking is not available at this apartment.

Does 2nd Story Historic Downtown 2BR with Modern Amenities have a pool?

This apartment does not have a pool.

Does 2nd Story Historic Downtown 2BR with Modern Amenities have a spa?

There are no spa services available at this apartment.

How close is 2nd Story Historic Downtown 2BR with Modern Amenities to downtown Winchester?

This apartment is 0.2 mi away from Winchester.

2nd Story Historic Downtown 2BR with Modern Amenities Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 9 out of 13 reviews
Rating 8 - Good. 3 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 1 out of 13 reviews

9.4/10

Cleanliness

Reviews

8/10 Good

John J.

Liked: Cleanliness

Well worth the money

Great place to stay... i feel like it wasnt advertised as well as it could have been. We loved the gas fireplace. Was concerned about check-in as i hadnt heard from the owner, but within a day of our arrival i reached out and the owner was always fast and responsive at that point. Any concerns vanished. What a great location!
Stayed 2 nights in Nov 2024

10/10 Excellent

RADENE B.

Liked: Cleanliness

Great little place

My daughter and I had a wonderful stay. The rental had everything we needed. The location was close to everything.
Stayed 3 nights in Aug 2024

8/10 Good

Kyile M., Atlanta, GA

Liked: Cleanliness
Stayed 2 nights in Apr 2024

10/10 Excellent

Irvin C.

Liked: Cleanliness

Very nice

Love the place
Stayed 4 nights in Jul 2024

2/10 Terrible

Brad H.

Disliked: Cleanliness

Never got in!

Never had a bad VRBO experience until this one. We booked this property 2 weeks in advance of our trip but never heard from property owner until we reached out to personal number. By the time they got back with us about how to enter the property, it was too late for us to reasonably make our trip. We communicated as such and asked for a partial refund to which there was no reply. Enjoy your free pay day!! Disappointing and frustrating. Would not recommend
Stayed 1 night in Jun 2024

10/10 Excellent

Linda P.

Liked: Cleanliness

Interesting and unique- very clean!

Fantastic
Stayed 2 nights in May 2024

10/10 Excellent

Elizabeth W.

Liked: Cleanliness

Nice little apartment conveniently located

Great spot. Easy drive to outdoor activities. Several places to eat and drink nearby. Host very responsive. Hope to stay here again!
Stayed 3 nights in Apr 2024

10/10 Excellent

Brian M.

Liked: Cleanliness

Great location

We had a great stay, the unit has lots of charm and is very cozy. We enjoyed the walkability to great local shops and restaurants. It's within a short driving distance to other great areas to check out!
Stayed 3 nights in Oct 2023

10/10 Excellent

Angelique D.

Liked: Cleanliness

Historic charm.

Charming historic building. The floors creak and have a slight lean, as would be expected in a 150 yr old building. Modern comforts all located in historic downtown Winchester. Walking distance to boutique shopping, cafes and activities. Beds were comfy too.
Stayed 3 nights in Mar 2023

10/10 Excellent

Brandon

Stayed 1 night in Feb 2023

8/10 Good

Susan F.

Liked: Cleanliness

Awesome historic property

The host is most helpful. The staircase is a bit daunting. The historic building has charm with wifi convenience.
Stayed 5 nights in Oct 2022

10/10 Excellent

Mallory M.

Liked: Cleanliness

GREAT Experience

Susan and Joel were AMAZING to work with. They are responsive, kind and the apartment was amazing. The location was great, we were there during the summer concert series and we were right in the middle of it. Live music, food, drinks. We could walk everywhere we needed to go. It was perfect. I would definitely stay there again.
Stayed 2 nights in May 2022

10/10 Excellent

Max I.

Liked: Cleanliness

Lovely stay

This spot was great! Right in the middle of cute downtown Winchester! I would definitely recommend this spot to anyone!
Stayed 2 nights in Nov 2021