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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester cabin rentals

Exterior

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, (112 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 CA $143
CA $263 total
includes taxes & fees
Sep 17 - Sep 18
Unique Stay in a 1907 Log Cabin on The Kentucky River
Exterior detail

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, (77 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 CA $181
CA $345 total
includes taxes & fees
Oct 6 - Oct 7
1800’s Historical Log Cabin near I-75 Interstate
Exterior

3. 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, (126 reviews)
"The cabin was clean and just what we needed for our weekend trip."
United States
Emmalynn P.
The price is CA $123
CA $265 total
includes taxes & fees
Sep 20 - Sep 21
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Terrace/patio

4. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,053 reviews)
"Great place to stay."
United States
Monty
The price is CA $139
CA $153 total
includes taxes & fees
Sep 27 - Sep 28
Natural Bridge State Resort Park
Exterior

5. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (90 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 CA $169
CA $232 total
includes taxes & fees
Sep 23 - Sep 24
Mountain Memories Cabin
Exterior

6. 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, (8 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 CA $181
CA $309 total
includes taxes & fees
Sep 29 - Sep 30
Dappled Grey Cabin with hot tub at Red River Gorge
Exterior

7. Hot Tub Cabin with Epic Ridge Views - Blackhawk

Hot Tub Cabin with Epic Ridge Views - Blackhawk
Stanton
10.0 out of 10, Exceptional, (5 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 CA $165
CA $380 total
includes taxes & fees
Sep 17 - Sep 18
Hot Tub Cabin with Epic Ridge Views - Blackhawk
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.
The price is CA $146
CA $268 total
includes taxes & fees
Sep 21 - Sep 22
New, Cozy, Secluded Cabin
Exterior

9. "Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub

"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Stanton
9.0 out of 10, Wonderful, (23 reviews)
"Cabin was beautiful no complaints "
United States
Dana S.
The price is CA $121
CA $305 total
includes taxes & fees
Sep 17 - Sep 18
"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Exterior

10. 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, (37 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is CA $210
CA $376 total
includes taxes & fees
Sep 17 - Sep 18
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Exterior

11. Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (15 reviews)
"Fun place to stay for 2!"
United States
Bob R.
The price is CA $153
CA $427 total
includes taxes & fees
Sep 29 - Sep 30
Plum Crazy: Frenchburg Cabin on 1 Acre
Exterior

12. Hot Tub Dome with Epic Ridge Views - Cardinal Crest

Hot Tub Dome with Epic Ridge Views - Cardinal Crest
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"This place was perfect for what I needed, a little space from the world and back to nature. Will be back. "
United States
Danny P.
The price is CA $234
CA $436 total
includes taxes & fees
Sep 21 - Sep 22
Hot Tub Dome with Epic Ridge Views - Cardinal Crest
Exterior

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

Cozy RRG Cabin • King Beds • Hot Tub • Views
Stanton
10.0 out of 10, Exceptional, (381 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 CA $237
CA $417 total
includes taxes & fees
Sep 17 - Sep 18
Cozy RRG Cabin • King Beds • Hot Tub • Views
Exterior

14. 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 CA $184
CA $344 total
includes taxes & fees
Sep 21 - Sep 22
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Exterior

15. 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 CA $236
CA $387 total
includes taxes & fees
Sep 29 - Sep 30
The Lakeview Cabin and Highland Retreat
Exterior

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (60 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 CA $236
CA $279 total
includes taxes & fees
Sep 23 - Sep 24
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Exterior

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 CA $452
CA $677 total
includes taxes & fees
Sep 22 - Sep 23
Cabin in Kentucky Horse Country
Exterior

18. Private | Hot Tub | Stargazing | Mountain View

Private | Hot Tub | Stargazing | Mountain View
Stanton
10.0 out of 10, Exceptional, (2 reviews)
"Great for a nice weekend getaway! House was very clean and close to all the gift shops & activities!"
United States
Kiersten R.
The price is CA $172
CA $400 total
includes taxes & fees
Sep 17 - Sep 18
Private | Hot Tub | Stargazing | Mountain View
Exterior detail

19. 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, (178 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 CA $197
CA $360 total
includes taxes & fees
Sep 20 - Sep 21
Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
Exterior

20. 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, (335 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 CA $223
CA $401 total
includes taxes & fees
Sep 20 - Sep 21
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Clean, airy, and with an incredibly helpful staff."
Erik 1-night trip
Posted 2 hours ago
Elwood Hotel & Suites

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
3,727
Accommodation
241 Cabin Rentals
Lowest Price
CA $153
Highest Price
CA $677

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 CA $153 and CA $677 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 Cozy 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. Cozy 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 CA $153 per night.
Can I find log cabins in Winchester?
For lots of nature lovers, the ideal outdoor vacation isn't complete without bunking down in a cozy 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. Cozy 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 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 vacation 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 - Cozy Tiny Cabin. Nearby fishing and hiking are a few things to keep you busy during your stay.

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