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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester cabin rentals

A rustic cabin surrounded by dense greenery, with a stone wall in the foreground and a wooden staircase leading up to the entrance.

1. 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, (114 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 traveler
$167 nightly
The price is $194
Oct 25 - Oct 26
Total with taxes and fees
Unique Stay in a 1907 Log Cabin on The Kentucky River
A rustic log cabin with a front door, two windows, and a small porch.

2. 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, (82 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
$225 nightly
The price is $261
Oct 27 - Oct 28
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate
A rustic cabin with a stone chimney, a wooden deck, and a concrete pathway leading to the entrance.

3. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,103 reviews)
"Close to multiple trails and restaurants."
United States
Curtis
$96 nightly
The price is $106
Nov 8 - Nov 9
Total with taxes and fees
Natural Bridge State Resort Park
A small log cabin with a red door, surrounded by a grassy field and trees.

4. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
$450 nightly
The price is $489
Oct 18 - Oct 19
Total with taxes and fees
Cabin in Kentucky Horse Country
A small cabin surrounded by dense forest.

5. 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, (132 reviews)
"Super cute cabin! We enjoyed every minutes and will be back!"
United States
Heather A.
$182 nightly
The price is $201
Oct 29 - Oct 30
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
A rustic cabin with a metal roof, a deck, and a grill area.

6. 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, (341 reviews)
"I absolutely loved everything about this cabin! Can’t wait to book again! Very clean and relaxing!"
United States
Jacinda P.
$253 nightly
The price is $279
Oct 18 - Oct 19
Total with taxes and fees
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
A cabin with a wooden deck, multiple windows, and a stone wall.

7. Social Distance/127 Private Acres -Hot Tub -Wi-Fi

Social Distance/127 Private Acres -Hot Tub -Wi-Fi
Irvine
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful cabin with in the woods. The hot tub was amazing with powerful jets. All the amenities on site for a fire, grilling and full kitchen. Was extremely quiet at nighttime with fireflies everywhere. Wanted to ride the side by side that is on premise. We should have asked if that was an option. Christie was very proactive with directions and communication as well. We are looking to come back in October. The Woodman's."
United States
Justin W.
$314 nightly
The price is $325
Nov 1 - Nov 2
Total with taxes and fees
Social Distance/127 Private Acres -Hot Tub -Wi-Fi
A cabin with a covered porch, large windows, and a wooden exterior.

8. 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.
$175 nightly
The price is $192
Oct 25 - Oct 26
Total with taxes and fees
New, Cozy, Secluded Cabin
A rustic, container-style building with a gravel path leading to it, surrounded by trees.

9. 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, (139 reviews)
"Great location, and super unique!"
United States
JR C.
$247 nightly
The price is $272
Oct 18 - Oct 19
Total with taxes and fees
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
A cabin with a porch, surrounded by autumn trees.

10. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (96 reviews)
"Great little place , clean and comfortable quiet nice place to just relax for a few days and take in the fresh air"
United States
Jason B.
$170 nightly
The price is $187
Oct 19 - Oct 20
Total with taxes and fees
Mountain Memories Cabin
A rustic cabin with a porch, surrounded by trees.

11. 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 traveler
$188 nightly
The price is $194
Nov 3 - Nov 4
Total with taxes and fees
Larkspur Cabin with Hot Tub near Red River Gorge
A modern, dark blue, container-style building with large windows, surrounded by a rocky landscape and dense forest.

12. 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, (43 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
$230 nightly
The price is $253
Oct 18 - Oct 19
Total with taxes and fees
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
A rustic cabin with a deck and outdoor seating area, surrounded by dense forest.

13. Luxury Creekside Cabin Hot Tub | Red River Gorge

Luxury Creekside Cabin Hot Tub | Red River Gorge
Stanton
9.4 out of 10, Exceptional, (3 reviews)
"We had an amazing stay , would recommend!"
United States
Alex V.
$262 nightly
The price is $287
Nov 1 - Nov 2
Total with taxes and fees
Luxury Creekside Cabin Hot Tub | Red River Gorge
A cabin with a porch, surrounded by trees, under a cloudy sky.

14. The Willow Nest Cabin, Stone fireplace, Cornhole, Kayaks, Views, Porch

The Willow Nest Cabin, Stone fireplace, Cornhole, Kayaks, Views, Porch
Stanton
10.0 out of 10, Exceptional, (1 review)
"A great cabin with a scenic view, clean cabin, and easy check in!"
United States
Miranda F.
$230 nightly
The price is $253
Oct 19 - Oct 20
Total with taxes and fees
The Willow Nest Cabin, Stone fireplace, Cornhole, Kayaks, Views, Porch
A small, single-story building with a porch, a door, and a window.

15. 180 Acre Forrest Retreat, Private Trails, Natural Springs, Near Red River Gorge

180 Acre Forrest Retreat, Private Trails, Natural Springs, Near Red River Gorge
Stanton
$228 nightly
The price is $251
Nov 1 - Nov 2
Total with taxes and fees
180 Acre Forrest Retreat, Private Trails, Natural Springs, Near Red River Gorge
A cabin with a wooden deck, a covered porch, and a staircase leading to the entrance.

16. Private Mountain Top | Romantic Retreat | Hot Tub

Private Mountain Top | Romantic Retreat | Hot Tub
Stanton
$276 nightly
The price is $311
Oct 19 - Oct 20
Total with taxes and fees
Private Mountain Top | Romantic Retreat | Hot Tub
A wooden cabin with a metal roof, surrounded by trees, and a covered outdoor seating area.

17. 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
$271 nightly
The price is $274
Oct 20 - Oct 21
Total with taxes and fees
The Lakeview Cabin and Highland Retreat
A small, single-story wooden cabin with a porch and a front door, surrounded by a dark forest.

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (64 reviews)
"We had a blast. So clean and such a cute place. Would definitely go back again."
United States
Katie E.
$203 nightly
The price is $224
Oct 22 - Oct 23
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
A small blue cabin with a brown door, surrounded by autumn trees.

19. High Rock Hideaway Red River Gorge KY Couples Cabin, Hot Tub, Wifi, Pet Friendly

High Rock Hideaway Red River Gorge KY Couples Cabin, Hot Tub, Wifi, Pet Friendly
Stanton
10.0 out of 10, Exceptional, (34 reviews)
"Great little getaway!"
United States
Rachel K.
$214 nightly
The price is $236
Oct 26 - Oct 27
Total with taxes and fees
High Rock Hideaway Red River Gorge KY Couples Cabin, Hot Tub, Wifi, Pet Friendly
Exterior

20. 100 Acres, Creek, Sunset Overlook, Kayaks/Pond

100 Acres, Creek, Sunset Overlook, Kayaks/Pond
Stanton
$336 nightly
The price is $371
Nov 9 - Nov 10
Total with taxes and fees
100 Acres, Creek, Sunset Overlook, Kayaks/Pond
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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent
"Very nice hotel! Some renovations were going on, but nothing that hindered our stay. The water pressure in the shower was wonderful! Staff at front desk was super helpful when we checked in, Melissa."
Tammy 1-night trip
Posted 12 hours ago
Fairfield Inn & Suites by Marriott Lexington North

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,853
Accommodation
246 Cabin Rentals
Lowest Price
$106
Highest Price
$489

Frequently asked questions

What are the best cabins near Winchester?
Ranging from small and basic to those that are all about luxury, there are 602 cabins available in and around Winchester. A few of the most popular options are 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 $106 and $489 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?
After spending your day having fun in Mother Nature, head home to the impeccable style and comfort of a Winchester luxury cabin. Cabin - Hot Tub, Wifi, No Pet Fee - Beary Cozy is a perfect option if you'd love to treat yourself. You'll appreciate the deluxe amenities here, such as a deck and a spa tub. 2 Bed Cabin Hot Tub - Fire Pit is another sought-after stay. Make use of a deck, a spa tub and a good deal more.
What are the best river cabins near Winchester?
Spend your days relaxing near the water and your nights listening to it surging past at a river cabin near Winchester. Our top recommendation — Hot Tub, Wifi, Adventure - New Family Cabin. This riverside getaway offers nearby ecotour services and a queen bed. Or, spend your break at Cabin - Pet - Friendly And Great Location. On top of its gorgeous location, amenities here include pet-friendly facilities and a deck.
What are the best cabins with pools near Winchester?
Slip on your swimsuit and go for a dip at your leisure when you book one of our cabin rentals with a pool. Cozy East Bernstadt Cabin With Porch + Fishing Lake is a winning option. A porch and a patio are among the other amenities that'll help make your stay comfortable. Or, enjoy some time out 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 your vacation in nature but don't feel like wrestling with tarpaulins and tent poles, a cabin is the way to go. Book a few nights or longer at Cabin - Sits On 8 Private Acres, Hiking Trails At This Secluded Chalet Wi. This favorite comes with an oven, a stovetop and more. You can also experience comfort and outdoor fun in the perfect package at Cave Run Red River Gorge Cabin. A firepit and a garden are among this retreat's 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. Ditch the office cubicle for a few days in the great outdoors at Cabin - Private, Gated, Wall Of Windows. On-site watersports and a firepit are some amenities it comes with. Otherwise, forget all about work at Whispering Pine Cabin Unit 2 In The Rrg. Kick back here and take advantage of 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 $106 per night.
Can I find log cabins in Winchester?
Kick off your day with a hot coffee in your log cabin and then spend the rest of your time fishing and picnicking. Sound like your dream vacation? Then head for Big Rock Log Cabin, Beside Natural Bridge. Another wooden retreat that comes with ample charm and warmth is Hot Tub, Wifi, Adventure - Family Log Cabin. Activities like fishing and hiking will add to your memories here.
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 travelers. It offers amenities like a patio and a firepit. Cozy Secluded Cabin With Wi - Fi is another fabulous option. Quality conveniences such as a porch and a patio will help make your stay a comfortable one.
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 farther 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 nature-filled escape that won't cost a fortune, you can't beat a cabin. Visualize yourself waking up to the sounds of wildlife and sipping coffee on a private deck surrounded by stunning vistas. Stay in a cabin in Winchester to get away from the fast pace of modern life. Whether they're beachside, lakeside or up a mountain, cabins offer a uniquely relaxing experience for anyone needing a break.
What are the top nature cabins in Winchester?
Make a booking at Hot Tub, Wifi, Adventure - New Family Cabin and let all your troubles float downstream. Fun activities like nearby golfing and nearby fishing help make this river cabin in Winchester a top option. Cabin - Pet - Friendly And Great Location is another property where you can relax in nature. If you're in the mood for adventure, go nearby horse riding and hiking.
What are some of the best cabins near Bluegrass Heritage Museum in Winchester?
Secluded Getaway In Beautiful New Cabin Near Red River Gorge is popular cabin in Bluegrass Heritage Museum. Home comforts, a picture-perfect backdrop and access to activities such as nearby hiking and biking trails and nearby rock climbing help make it the ideal escape. Hot Tub, Wifi, Pet - Friendly - Cozy Tiny Cabin also combines nature and adventure. Spend your stay here and add nearby fishing and nearby kayaking to your to-do list.

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