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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Our top choices for Winchester cabin rentals

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 $144
CA $265 total
includes taxes & fees
Aug 9 - Aug 10
Unique Stay in a 1907 Log Cabin on The Kentucky River

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, (74 reviews)
"Very cool historical home. Nice and clean!"
United States
Julie L.
The price is CA $182
CA $353 total
includes taxes & fees
Aug 18 - Aug 19
1800’s Historical Log Cabin near I-75 Interstate

3. Hike on Inn!

Hike on Inn!
Clay City
The price is CA $145
CA $395 total
includes taxes & fees
Aug 3 - Aug 4
Hike on Inn!

4. 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, (120 reviews)
"great place!"
United States
Ava G.
The price is CA $137
CA $286 total
includes taxes & fees
Aug 24 - Aug 25
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

5. 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 CA $113
CA $218 total
includes taxes & fees
Aug 2 - Aug 3
Larkspur Cabin with Hot Tub near Red River Gorge

6. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,980 reviews)
"Clean room and good continental breakfast."
United States
Jeff
The price is CA $127
CA $140 total
includes taxes & fees
Aug 31 - Sep 1
Natural Bridge State Resort Park

7. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (86 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 $183
CA $265 total
includes taxes & fees
Aug 3 - Aug 4
Mountain Memories Cabin

8. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.4 out of 10, Very good, (7 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is CA $147
CA $270 total
includes taxes & fees
Aug 10 - Aug 11
New, Cozy, Secluded Cabin

9. 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 $208
CA $404 total
includes taxes & fees
Aug 5 - Aug 6
Hot Tub Dome with Epic Ridge Views - Cardinal Crest

10. 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 $455
CA $682 total
includes taxes & fees
Aug 2 - Aug 3
Cabin in Kentucky Horse Country

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (52 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is CA $238
CA $300 total
includes taxes & fees
Aug 5 - Aug 6
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

12. Hot Tub Dome with Epic Ridge Views- Hickory Heights

Hot Tub Dome with Epic Ridge Views- Hickory Heights
Stanton
10.0 out of 10, Exceptional, (5 reviews)
"Such a fun and unique property! It was great for a birthday/date getaway weekend!! "
United States
Lindsey C.
The price is CA $203
CA $397 total
includes taxes & fees
Aug 5 - Aug 6
Hot Tub Dome with Epic Ridge Views- Hickory Heights

13. Tiny Cabin At The Pond

Tiny Cabin At The Pond
Stanton
9.4 out of 10, Exceptional, (22 reviews)
"Loved the friendly Donkeys! Very relaxing location."
United States
Sharon C.
The price is CA $220
CA $277 total
includes taxes & fees
Aug 5 - Aug 6
Tiny Cabin At The Pond

14. Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.4 out of 10, Very good, (37 reviews)
"Beautiful little cabin"
United States
Ryan W.
Quaint, heavily forested cabin, mountain valley view.

15. BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (326 reviews)
"The hot tub was very nice and a very private "
United States
Donnie W.
The price is CA $225
CA $407 total
includes taxes & fees
Aug 5 - Aug 6
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

16. Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge

Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (13 reviews)
"Great cabin, awesome hot tub. Amazing experience"
United States
Brian E.
The price is CA $168
CA $371 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge

17. Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
Irvine
9.8 out of 10, Exceptional, (18 reviews)
"Cute little cabin off the beaten path. Great for a couples getaway or as a hang out space."
United States
Tricia H.
The price is CA $133
CA $300 total
includes taxes & fees
Aug 17 - Aug 18
Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

18. "Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (15 reviews)
"Great location "
United States
Zach M.
The price is CA $136
CA $312 total
includes taxes & fees
Aug 5 - Aug 6
"Rocky Top" - Cozy RRG Cabin

19. Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (14 reviews)
"Fun place to stay for 2!"
United States
Bob R.
The price is CA $141
CA $415 total
includes taxes & fees
Aug 3 - Aug 4
Plum Crazy: Frenchburg Cabin on 1 Acre

20. YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (374 reviews)
"What a cool place to stay! When we come back to RRG area, we will definitely stay here again."
United States
Deborah H.
The price is CA $237
CA $422 total
includes taxes & fees
Aug 13 - Aug 14
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
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

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
3,294
Accommodation
234 Cabin Rentals
Lowest Price
CA $140
Highest Price
CA $682

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 $140 and CA $682 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 $140 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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