MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Winchester holiday rentals

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is HK$1,164
HK$2,423 total
includes taxes & fees
13 Jun - 14 Jun
The Winchester
Fridge, microwave, oven, stovetop

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is HK$1,164
HK$2,415 total
includes taxes & fees
11 Jun - 12 Jun
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Property grounds

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
Stanton
9.4 out of 10, Exceptional, (16 reviews)
"Fun for the family!"
United States
Jennifer
The price is HK$465
HK$983 total
includes taxes & fees
11 Jun - 12 Jun
Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
Fridge, microwave, oven, stovetop

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (50 reviews)
"Very nice area and quiet. Outside of the home looked a bit rough. Inside was clean and organized with everything you would need to be comfortable. The owner was very responsive and informative. It was a very fun stay. Stanton is a beautiful town with lots of outdoor activities. I highly recommend booking here at the Towner. We will be booking again next year."
United States
Darren
The price is HK$697
HK$1,671 total
includes taxes & fees
21 Jun - 22 Jun
Conveniently Located ~ WiFi ~ Central Heat & Air.
Living area

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,921 reviews)
"Great area Nice place to stay"
United States
Julie
The price is HK$924
HK$1,018 total
includes taxes & fees
14 Jun - 15 Jun
Natural Bridge State Resort Park
Property grounds

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (107 reviews)
"This was a wonderful location and a delightfully cozy cabin for a couple or a solo stay. Might very well stay here again in the future."
United States
Jason H.
The price is HK$691
HK$1,514 total
includes taxes & fees
15 Jun - 16 Jun
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Property grounds

Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.2 out of 10, Very good, (33 reviews)
"Beautiful little cabin"
United States
Ryan W.
The price is HK$831
HK$1,604 total
includes taxes & fees
11 Jun - 12 Jun
Quaint, heavily forested cabin, mountain valley view.
Interior

"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (14 reviews)
"Great location "
United States
Zach M.
The price is HK$847
HK$1,689 total
includes taxes & fees
11 Jun - 12 Jun
"Rocky Top" - Cozy RRG Cabin
Terrace/patio

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (46 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is HK$1,333
HK$1,604 total
includes taxes & fees
16 Jun - 17 Jun
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Smart TV, fireplace, books

Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (112 reviews)
"This is a unique property, it feels like stepping into history. It is well maintained, clean and comfortable but not your average stay! "
United States
Jennie C.
Unique Stay in a 1907 Log Cabin on The Kentucky River
TV, fireplace

Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
The price is HK$705
HK$1,435 total
includes taxes & fees
16 Jun - 17 Jun
Dappled Grey Cabin with hot tub at Red River Gorge
Terrace/patio

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (130 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
The price is HK$1,258
HK$2,234 total
includes taxes & fees
14 Jun - 15 Jun
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Smart TV, fireplace, books

1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (69 reviews)
"Excellent stopover. "
United States
Robert W.
The price is HK$1,019
HK$1,692 total
includes taxes & fees
18 Jun - 19 Jun
1800’s Historical Log Cabin near I-75 Interstate
Terrace/patio

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (76 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is HK$1,058
HK$1,529 total
includes taxes & fees
16 Jun - 17 Jun
Mountain Memories Cabin
Terrace/patio

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (35 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is HK$1,023
HK$1,473 total
includes taxes & fees
17 Jun - 18 Jun
Mountaintop Cottage
Interior

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveller
The price is HK$1,246
HK$2,658 total
includes taxes & fees
11 Jun - 12 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Outdoor spa tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
Stanton
10.0 out of 10, Exceptional, (7 reviews)
"Yes, I brought my tiny dog and she loved it there as much as we did! "
United States
Kimberly J.
The price is HK$1,058
HK$2,546 total
includes taxes & fees
11 Jun - 12 Jun
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
Outdoor dining

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Stanton
8.6 out of 10, Excellent, (61 reviews)
"Very cozy and an amazing stay!"
United States
Sam P.
The price is HK$1,371
HK$1,879 total
includes taxes & fees
18 Jun - 19 Jun
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
1 bedroom, iron/ironing board, travel cot, WiFi

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
The price is HK$1,253
HK$2,240 total
includes taxes & fees
14 Jun - 15 Jun
"Cardinal Crest" - Overlook Dome 002 in RRG
Fridge, microwave, oven, stovetop

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
Stanton
9.6 out of 10, Exceptional, (23 reviews)
"Beautiful cabin and property, very quiet and surely secluded. Very clean and decorated, stocked well with cooking utensils. We will definitely make plans to visit again!"
United States
Kevin S.
Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

The Campbell House Lexington, Curio Collection by Hilton

The Campbell House Lexington, Curio Collection by Hilton

4/10 Poor
"The place is dirty and needs some TLC"
Karen 2-night trip
Posted less than an hour ago
The Campbell House Lexington, Curio Collection by Hilton

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Near Kentucky State Horse Park 💛The Yalla House🚪 🏇🏼Horse & Bourbon Central🥃: This holiday home rental outside of Winchester is located in a rural location, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Winchester?

Expedia has 5 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail are other places to visit while you're in town.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.