An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester cabin rentals

A rustic log cabin with a front door, two windows, and a small porch.

1. 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, (79 reviews)
"The property is so cool! It has so much history within it. We loved just walking around and looking at the small details. It was cozy and comfy. The property was easy to find and we were given clear instructions for check in and such."
United States
Sarah
The price is NZ$442
includes taxes & fees
28 Sept - 29 Sept
1800’s Historical Log Cabin near I-75 Interstate
A rustic cabin surrounded by dense greenery, with a stone wall in the foreground and a wooden staircase leading up to the entrance.

2. 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, (113 reviews)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveller
The price is NZ$333
includes taxes & fees
29 Sept - 30 Sept
Unique Stay in a 1907 Log Cabin on The Kentucky River
A wooden cabin with a porch, surrounded by trees and a gravel driveway.

3. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
9.8 out of 10, Exceptional, (96 reviews)
"The property was very clean and nice for our stay. The only complaint was that the main cabin was pretty hot and the wall unit was not able to cool the living room/main living space down. It doesn’t help that it has been 90 degrees though, so I’m sure this place is 5 stars during the fall!"
United States
Kamryn
The price is NZ$446
includes taxes & fees
28 Sept - 29 Sept
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
A rustic cabin with a porch, surrounded by trees.

4. Larkspur Cabin with Hot Tub near Red River Gorge

Larkspur Cabin with Hot Tub near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (11 reviews)
"My wife and I had a very relaxing get away. Lovely place for a couple."
United States
Anonymous traveller
The price is NZ$280
includes taxes & fees
29 Sept - 30 Sept
Larkspur Cabin with Hot Tub near Red River Gorge
A rustic cabin with a stone chimney, a wooden deck, and a concrete pathway leading to the entrance.

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,064 reviews)
"Great place to stay."
United States
Monty
The price is NZ$180
includes taxes & fees
30 Sept - 1 Oct
Natural Bridge State Resort Park
A cabin with a porch, surrounded by autumn trees.

6. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (92 reviews)
"Our second visit here. Host very responsive, location great and very clean. Would recommend to anyone looking to visit the area."
United States
Robert C.
The price is NZ$346
includes taxes & fees
7 Oct - 8 Oct
Mountain Memories Cabin
A cabin with a covered porch, large windows, and a wooden exterior.

7. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.0 out of 10, Very good, (8 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is NZ$340
includes taxes & fees
27 Sept - 28 Sept
New, Cozy, Secluded Cabin

8. NEW, Promo Pricing - Luxury Woodland Loft Retreat @ Red River Gorge

NEW, Promo Pricing - Luxury Woodland Loft Retreat @ Red River Gorge
Stanton
9.4 out of 10, Exceptional, (6 reviews)
"Excellent location and cool place to relax. "
United States
Arthur G.
The price is NZ$445
includes taxes & fees
28 Sept - 29 Sept
NEW, Promo Pricing - Luxury Woodland Loft Retreat @ Red River Gorge
A modern house with a well-lit porch and outdoor seating area.

9. Cozy RRG Cabin • King Beds • Hot Tub • Views

Cozy RRG Cabin • King Beds • Hot Tub • Views
Stanton
10.0 out of 10, Exceptional, (383 reviews)
"This was a great spot to stay on our visit to RRG area it’s conveniently located and lots of space for our family of three would recommend to anyone"
United States
Al M.
The price is NZ$503
includes taxes & fees
27 Sept - 28 Sept
Cozy RRG Cabin • King Beds • Hot Tub • Views
A two-story cabin with a wooden deck and a balcony, surrounded by trees.

10. Hot Tub Cabin with Epic Ridge Views - Blackhawk

Hot Tub Cabin with Epic Ridge Views - Blackhawk
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Our family had a great time! Amazing views and they were quick to respond if we had a question. "
United States
Tonya R.
The price is NZ$948
includes taxes & fees
26 Sept - 27 Sept
Hot Tub Cabin with Epic Ridge Views - Blackhawk
A rustic, container-style building with a gravel path leading to it, surrounded by trees.

11. Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge

Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Stanton
10.0 out of 10, Exceptional, (136 reviews)
"Great location, and super unique!"
United States
JR C.
The price is NZ$453
includes taxes & fees
27 Sept - 28 Sept
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
A rustic cabin with a metal roof, a deck, and a grill area.

12. Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods

Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
Stanton
10.0 out of 10, Exceptional, (337 reviews)
"I absolutely loved everything about this cabin! Can’t wait to book again! Very clean and relaxing!"
United States
Jacinda P.
The price is NZ$465
includes taxes & fees
27 Sept - 28 Sept
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
A wooden cabin with a metal roof, surrounded by trees, and a covered outdoor seating area.

13. The Lakeview Cabin and Highland Retreat

The Lakeview Cabin and Highland Retreat
Clay City
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful! Clean! Smells and sounds were amazing for us country folk. Much love!"
United States
Nathaniel
The price is NZ$469
includes taxes & fees
28 Sept - 29 Sept
The Lakeview Cabin and Highland Retreat
A modern, dark blue, container-style building with large windows, surrounded by a rocky landscape and dense forest.

14. Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape

Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Stanton
10.0 out of 10, Exceptional, (39 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is NZ$440
includes taxes & fees
27 Sept - 28 Sept
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
A rustic building with a sign that reads "Welcome to Rocky Top in the beautiful Red River Gorge."

15. "Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.4 out of 10, Exceptional, (17 reviews)
"Great location "
United States
Zach M.
The price is NZ$382
includes taxes & fees
28 Sept - 29 Sept
"Rocky Top" - Cozy RRG Cabin
A small, dark-colored cabin with multiple windows, string lights, and a gravel path leading to it.

16. Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape

Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
Stanton
10.0 out of 10, Exceptional, (179 reviews)
"I was ideal get away for us the hot tub was perfect just what I need. Perfect location to everything we wanted to do."
United States
Laura H.
The price is NZ$453
includes taxes & fees
27 Sept - 28 Sept
Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
A small log cabin with a red door, surrounded by a grassy field and trees.

17. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
The price is NZ$857
includes taxes & fees
13 Oct - 14 Oct
Cabin in Kentucky Horse Country
A two-story log cabin with a front porch, a covered entryway, and a landscaped yard.

18. Arch Fun Cabin - Modern Cabin w/ Hot Tub, Games & Views

Arch Fun Cabin - Modern Cabin w/ Hot Tub, Games & Views
Stanton
10.0 out of 10, Exceptional, (2 reviews)
"This is such a beautiful home! We loved the hot tub, the arcade games, the pool table, the beautiful kitchen…it truly is a peaceful spacious house! The house sits on top of a hill which gave a feeling of privacy and peace, with trees and birds all around. The bedrooms are comfortable and there are lots of areas for everyone to hang out. Thank you for hosting our vacation! "
United States
Wendy J.
The price is NZ$760
includes taxes & fees
29 Sept - 30 Sept
Arch Fun Cabin - Modern Cabin w/ Hot Tub, Games & Views
A cozy cabin interior with a sofa, a fireplace, a television, and a warning sign for a bigfoot area.

19. 3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.8 out of 10, Exceptional, (9 reviews)
"Remote and nice location with plenty of room. "
United States
Keith P.
The price is NZ$423
includes taxes & fees
28 Sept - 29 Sept
3 Miles Hollerwood/ATV Parking/Mountain Views
A small, single-story wooden cabin with a porch and a front door, surrounded by a dark forest.

20. Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (61 reviews)
"This was one of the best places I have stayed using VRBO. Everything was 5/5 stars. Host was great at communication and the cabin was extremely clean with all you need for a cabin getaway."
United States
Nicholas W.
The price is NZ$369
includes taxes & fees
8 Oct - 9 Oct
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
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

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

10/10 Excellent
"Very clean, cute and the restaurant is good."
Casey 2-night trip
Posted 3 hours ago
Origin Lexington a Wyndham Hotel

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
3,721
Accommodation
241 Cabin Rentals
Lowest Price
NZ$180
Highest Price
NZ$948

Frequently asked questions

What are the best cabins near Winchester?
Ranging from rustic and small to large and luxurious, you have 607 cabins on offer in and around Winchester. Some popular options include Secluded Red River Gorge Pet - Friendly Cabin On 3 Acres - Serenity Falls and Cabin - Secluded With Best Views In E. Ky. Can See 3 States. You Won't Be Disappointed.
Are there cheap cabins in Winchester?
Priced between NZ$180 and NZ$948 per night, escaping the everyday has never been so affordable. Snap up one of our cheap cabins in Winchester and experience the great outdoors without emptying your bank account.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best luxury cabins near Winchester?
Get set to treat yourself to a stay to remember at one of our Winchester luxury cabins. Cabin - Hot Tub, Wifi, No Pet Fee - Beary Cosy is one place where you can spend a few days or more living the high life. It features a deck and a spa tub. Or, use 2 Bed Cabin Hot Tub - Fire Pit as a base to explore the impressive natural areas around you. Quality touches here include a deck and a spa tub.
What are the best river cabins near Winchester?
If you're seeking a comfy hideaway by the water, a Winchester river cabin will be just the thing. Put your feet up at Hot Tub, Wifi, Adventure - New Family Cabin and let any worries on your mind disappear downstream. Handy amenities here include nearby ecotour services and a queen bed. Another top riverside property is Cabin - Pet - Friendly And Great Location. Guests have use of pet-friendly facilities, a deck and more.
What are the best cabins with pools near Winchester?
Slip on your swimsuit and go for a dip whenever you want when you stay at one of our cabin rentals with a pool near Winchester. Cosy East Bernstadt Cabin With Porch + Fishing Lake is a favourite among travellers. A porch and a patio are some other amenities you'll find here. Or you can enjoy a break from the hustle and bustle at Cabin With A Pool, Hot Tub And Wi. As well as a pool, this cabin comes with a swimming pool and a patio.
What are some great Winchester cabins?
When you want to spend some time out in nature but aren't into roughing it, a cabin is a perfect solution. Book a few nights or longer at Cabin - Sits On 8 Private Acres, Hiking Trails At This Secluded Chalet Wi. This property comes with an oven, a stovetop and more. You can also experience comfort and outdoor fun rolled into one at Cave Run Red River Gorge Cabin. A firepit and a garden are among its amenities.
What are the best weekend cabin rentals in Winchester?
It doesn't get much better than a weekend cabin getaway after a long week at work. Swap your cramped office for a few days in the great outdoors at Hot Tub, Wifi, Adventure - New Family Cabin. A porch and a patio are some of the amenities it comes with. Alternatively, forget all about work at Secluded Cabin On 70 Acres Private Land. Put your bags down here and enjoy access to a patio and a firepit.
What are the best cabin prices in Winchester?
Whether you're on a budget or want to splash out on your next trip, you'll find what you're looking for on Expedia. At the moment, you can get a Winchester cabin from only NZ$180 per night.
Can I find log cabins in Winchester?
For lots of nature lovers, the ideal outdoor holiday isn't complete without bunking down in a cosy log cabin. Get exploring or simply slow down and relax at Big Rock Log Cabin, Beside Natural Bridge. Recreational activities such as picnicking and hiking are within easy reach here. Another attractive log cabin getaway is Hot Tub, Wifi, Adventure - Family Log Cabin. Canoeing and quad biking will keep you active when you're not happily hibernating in your rustic hideaway.
What are the highest-rated cabins in Winchester?
With an impressive rating, it's easy to see why Cave Run Red River Gorge Cabin is a huge hit with Expedia cabin travellers. Some amenities here include a patio and a firepit. Cosy Secluded Cabin With Wi - Fi is another fantastic choice. Conveniences such as a porch and a patio will help make your stay happy and comfortable.
What are the top things to see and do in Winchester?
If you'd like to do some sightseeing around Winchester, don't miss Community Park. In the mood for a road trip? Rent a car and head to attractions a little further afield, including Cassell Creek Golf Course. There's a great big world to experience outside your comfy cabin!
Why should I book a cabin in Winchester?
For a holiday that's big on charm, value for money and home comforts, a cabin is the best choice. Leave your city blues behind and wander through the greenery of nature. From days spent hiking to peaceful nights cuddled up by the fire, cabins offer both excitement and relaxation. Check out all the great Winchester options right here on Expedia.
What are the top nature cabins in Winchester?
Escape to Hot Tub, Wifi, Adventure - New Family Cabin and let all your worries drift downstream. Activities such as nearby rock climbing and cycling help make this river cabin in Winchester a hit with travellers. Cabin - Pet - Friendly And Great Location is another getaway where you can hang out in nature. If you're in the mood for adventure, try nearby mountain biking and nearby fishing.
What are some of the best cabins near Bluegrass Heritage Museum in Winchester?
Leave the noisy city behind and venture into nature from a Bluegrass Heritage Museum cabin. Get up close to wildlife, take in the fresh air and then settle back at Secluded Getaway In Beautiful New Cabin Near Red River Gorge. Popular activities such as paddle boating and nearby fishing are mere moments away here. Another place where you'll feel right at home is Hot Tub, Wifi, Pet - Friendly - Cosy Tiny Cabin. Nearby fishing and hiking are a few things to keep you busy during your stay.

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