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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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 traveller
The price is €168
includes taxes & fees
6 Dec - 7 Dec
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, (85 reviews)
"Great location and home for our 10 year anniversary"
United States
Christopher S.
The price is €228
includes taxes & fees
8 Nov - 9 Nov
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, (2,133 reviews)
"Love staying here, such easy access to the Gorge and Natural Bridge. Always convenient and easy to deal with. Always a place I keep in mind when I’m staying in the area."
United States
Logan
The price is €68
includes taxes & fees
6 Dec - 7 Dec
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.
The price is €417
includes taxes & fees
8 Nov - 9 Nov
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, (133 reviews)
"It was a great cozy place for a weekend for me and my sister. It had everything we needed and we especially loved having the window bed! Would definitely consider staying here again."
United States
Anonymous traveller
The price is €170
includes taxes & fees
11 Nov - 12 Nov
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
A rustic cabin with a porch, surrounded by trees.

6. 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 €150
includes taxes & fees
8 Nov - 9 Nov
Larkspur Cabin with Hot Tub near Red River Gorge
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
9.6 out of 10, Exceptional, (4 reviews)
"This place is the definition of seclusion. It is so peaceful here. Very nice cabin with plenty of room for a family or a few friends. Only 30 minutes from the gorge and it was a pleasant drive to get there with many options to eat and shop. I highly recommend Toads BarN grill and definitely Miguel’s pizza. The hot tub was a fantastic treat to come back to after long days of hiking. It was very clean and heated up waiting for us. Very secluded and you hear nothing but the sounds of nature. Beds...
United States
Tyler N.
The price is €288
includes taxes & fees
8 Nov - 9 Nov
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
8.4 out of 10, Very good, (9 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
New, Cozy, Secluded Cabin
A cabin with a porch, surrounded by autumn trees.

9. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (99 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.
The price is €180
includes taxes & fees
5 Dec - 6 Dec
Mountain Memories Cabin
A rustic cabin with a metal roof, a deck, and a grill area.

10. 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, (344 reviews)
"great secluded property with everything we needed for a great weekend. Hot Tub was nice after a day of hiking."
United States
Kenneth
The price is €264
includes taxes & fees
16 Nov - 17 Nov
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
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, (141 reviews)
"The room was so cozy and clean! The host was super communicative."
United States
Vamsidhar S.
The price is €242
includes taxes & fees
15 Nov - 16 Nov
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
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, (47 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is €233
includes taxes & fees
8 Nov - 9 Nov
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
A wooden cabin with a deck, a staircase, and a door.

13. Trailer Parking/Hot Tub/King Size Beds/Mt Views

Trailer Parking/Hot Tub/King Size Beds/Mt Views
Stanton
10.0 out of 10, Exceptional, (1 review)
"Here’s a polished version of your review:We had a wonderful stay at this cabin with another couple. The accommodations were excellent — comfortable, clean, and very well stocked with everything we needed. It truly felt like a hidden gem, especially with the ample parking space for our trailers, which can be hard to find. We loved relaxing around the fire pit in the evenings after a long day. We thoroughly enjoyed our stay and will definitely be coming back soon!"
United States
Sarah G.
The price is €261
includes taxes & fees
16 Nov - 17 Nov
Trailer Parking/Hot Tub/King Size Beds/Mt Views
A small, single-story wooden cabin with a porch and a front door, surrounded by a dark forest.

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (67 reviews)
"Best cabin I have ever stayed at."
United States
Richard D.
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
A small cabin with a wooden deck and a metal roof, surrounded by trees.

15. Luxury Cabin with Pasture Views & Private Hot Tub

Luxury Cabin with Pasture Views & Private Hot Tub
STANTON
8.0 out of 10, Very good, (2 reviews)
"Great visit in a wonderful area. We had a terrific time exploring the area in a very comfortable home. You might want to bring some extra towels as we had barely enough for our visit."
United States
Anonymous traveller
The price is €241
includes taxes & fees
8 Nov - 9 Nov
Luxury Cabin with Pasture Views & Private Hot Tub
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, (183 reviews)
"Loved the secluded atmosphere"
United States
Andrea
The price is €233
includes taxes & fees
8 Nov - 9 Nov
Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
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, (3 reviews)
"The cabin is super clean, were some games and the pedalboat for lake was a great addition! Definitely a perfect couples get away . Quiet, Great Lake/mountain view! Was as described and was reasonably priced! Highly recommended and would stay again! Host was wonderful and answered every question with quick response."
United States
Randy P.
The Lakeview Cabin and Highland Retreat
A modern house with a well-lit porch and outdoor seating area.

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

Cozy RRG Cabin • King Beds • Hot Tub • Views
Stanton
10.0 out of 10, Exceptional, (391 reviews)
"The whole stay was awesome.. will definitely be back...😍😍😍"
United States
Edith
The price is €263
includes taxes & fees
9 Nov - 10 Nov
Cozy RRG Cabin • King Beds • Hot Tub • Views
A rustic cabin with a porch, a flag, and a small table and chairs.

19. 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
180 Acre Forrest Retreat, Private Trails, Natural Springs, Near Red River Gorge
Exterior

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

100 Acres, Creek, Sunset Overlook, Kayaks/Pond
Stanton
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

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Would definitely come back. Rooms were clean. Smelled good. Breakfast was included and has a restaurant on site. Other food choices are available in the area. Close to many tourist attractions . There is a bar on site, friendliest bar in Red River Gourge. Can't say enough would come back for sure"
Michelle 1-night trip
Posted 1 hour ago
Natural Bridge State Resort Park

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
3,708
Accommodation
246 Cabin Rentals
Lowest Price
€68
Highest Price
€417

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 €68 and €417 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 €68 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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