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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Winchester cabin rentals

View from room
Natural Bridge State Resort Park

Cabin in Slade

Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1785)
"Front desk staff was super nice, room was perfect as we were hiking and needed a place to relax and get some sleep! "
United States
Kathy
Natural Bridge State Resort Park
Exterior
Dappled Grey Cabin with hot tub at Red River Gorge

Cabin in Stanton

Dappled Grey Cabin with hot tub at Red River Gorge
2.0 star property
10.0 out of 10, Exceptional, (5)
"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 HK$715
HK$1,412 total
includes taxes & fees
28 Dec - 29 Dec
Dappled Grey Cabin with hot tub at Red River Gorge
Exterior
Quaint, heavily forested cabin, mountain valley view.

Cabin in Slade

Quaint, heavily forested cabin, mountain valley view.
2.0 star property
8.2 out of 10, Very good, (26)
"Cabin was good but other cabins are close cabin was very comfortable road to cabin is very steep but doable "
United States
Terry
The price is HK$816
HK$1,582 total
includes taxes & fees
1 Jan - 2 Jan 2026
Quaint, heavily forested cabin, mountain valley view.
Exterior
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

Cabin in Stanton

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
2.0 star property
9.8 out of 10, Exceptional, (15)
"Overall the cabin was very nice. There were some minor maintenance issues, such as the electric fireplace not working and the remotes for the tv needing batteries, but it was a great cabin. We enjoyed our stay. "
United States
Anonymous traveller
The price is HK$1,259
HK$2,810 total
includes taxes & fees
6 Jan - 7 Jan 2026
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Terrace/patio
Hot Tub! Tiny Cabin Retreat near RRG

Cabin in Stanton

Hot Tub! Tiny Cabin Retreat near RRG
2.0 star property
7.4 out of 10, Good, (8)
"Nice calm and nice cabin and was cozy I had fun for my birthday overall great experience "
United States
MainSlime
The price is HK$553
HK$1,381 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub! Tiny Cabin Retreat near RRG
Exterior
Hot Tub! Tiny House Retreat in the Woods

Cabin in Stanton

Hot Tub! Tiny House Retreat in the Woods
2.0 star property
7.2 out of 10, Good, (5)
"Overall, great stay! The tiny house looked just like the photos and the hot tub was added relaxation. Lots of hiking options in the area that we were able to explore!The only heads up would be that the drive back to the cabin is gravel, bumpy, and mainly uphill…so if you don’t have a vehicle that can handle it, it could be tricky. Our Jeep made it just fine though!"
United States
Jaimie K.
The price is HK$653
HK$1,405 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hot Tub! Tiny House Retreat in the Woods
Exterior
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

Cabin in Frenchburg

Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
9.8 out of 10, Exceptional, (17)
"This cabin was beautiful! It had everything we needed! Comfortable stay, family friendly! Wish we would have had more time to stay and can’t wait to come back!"
United States
Kristen W.
The price is HK$904
HK$2,176 total
includes taxes & fees
25 Jan - 26 Jan 2026
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
Exterior
Tranquil Getaway in the Woods ~ Sunset Ridge

Cabin in Irvine

Tranquil Getaway in the Woods ~ Sunset Ridge
10.0 out of 10, Exceptional, (84)
"Beautiful, secluded and spacious "
United States
Shannon H.
The price is HK$734
HK$1,067 total
includes taxes & fees
4 Jan - 5 Jan 2026
Tranquil Getaway in the Woods ~ Sunset Ridge
Exterior
New, Cozy, Secluded Cabin

Cabin in Jeffersonville

New, Cozy, Secluded Cabin
2.0 star property
8.0 out of 10, Very good, (4)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is HK$816
HK$1,449 total
includes taxes & fees
27 Jan - 28 Jan 2026
New, Cozy, Secluded Cabin
Exterior detail
"Rocky Top" - Cozy RRG Cabin

Cabin in Stanton

"Rocky Top" - Cozy RRG Cabin
9.0 out of 10, Wonderful, (12)
"Great place to stay! Super close to RRG and the DBBB. Also just a few minutes for Miguel’s for the BEST pizza!"
United States
Mallory H.
The price is HK$822
HK$1,746 total
includes taxes & fees
8 Jan - 9 Jan 2026
"Rocky Top" - Cozy RRG Cabin
Microwave, oven, stovetop
NEW, Promo Pricing - Karmic Loft Woodland Escape

Cabin in Stanton

NEW, Promo Pricing - Karmic Loft Woodland Escape
9.6 out of 10, Exceptional, (4)
"Excellent location and cool place to relax. "
United States
Arthur G.
The price is HK$901
HK$1,730 total
includes taxes & fees
1 Jan - 2 Jan 2026
NEW, Promo Pricing - Karmic Loft Woodland Escape
Exterior
Just 1 mile from Natural Bridge State Park!

Cabin in Slade

Just 1 mile from Natural Bridge State Park!
8.6 out of 10, Excellent, (27)
"Just a lil family getaway before the school year starts and Bear Cub cabin was absolutely perfect for our family of five! "
United States
Michael F.
The price is HK$955
HK$1,863 total
includes taxes & fees
2 Jan - 3 Jan 2026
Just 1 mile from Natural Bridge State Park!
Exterior
Hot Tub, WiFi & Pet-Friendly - Pilot Point

Cabin in Stanton

Hot Tub, WiFi & Pet-Friendly - Pilot Point
9.6 out of 10, Exceptional, (162)
"Cabin was adorable. It was the perfect getaway for my husband and me. "
United States
Danielle
The price is HK$933
HK$2,034 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub, WiFi & Pet-Friendly - Pilot Point
Exterior
Mountain Memories Cabin

Cabin in Stanton

Mountain Memories Cabin
10.0 out of 10, Exceptional, (61)
"Great cabin!!"
United States
Amanda S.
The price is HK$1,127
HK$1,611 total
includes taxes & fees
28 Dec - 29 Dec
Mountain Memories Cabin
Exterior
The DEN Shipping Container Cabin-HotTub!-High Speed WiFi!-Great View & Location!

Cabin in Stanton

The DEN Shipping Container Cabin-HotTub!-High Speed WiFi!-Great View & Location!
10.0 out of 10, Exceptional, (117)
"Nice clean and private with a great view."
United States
James B.
The price is HK$1,208
HK$2,154 total
includes taxes & fees
28 Dec - 29 Dec
The DEN Shipping Container Cabin-HotTub!-High Speed WiFi!-Great View & Location!
Exterior
CREEKSIDE CABIN

Cabin in Stanton

CREEKSIDE CABIN
7.6 out of 10, Good, (5)
"Cute and cozy and very clean."
United States
Sheena P.
The price is HK$944
HK$1,803 total
includes taxes & fees
30 Dec - 31 Dec
CREEKSIDE CABIN
Exterior
A Frame of Mind - near Red River Gorge KY

Cabin in Jeffersonville

A Frame of Mind - near Red River Gorge KY
9.2 out of 10, Wonderful, (69)
"This place was perfect for me and my two kids. "
United States
Lindsey B.
The price is HK$847
HK$1,643 total
includes taxes & fees
4 Jan - 5 Jan 2026
A Frame of Mind - near Red River Gorge KY
Exterior
The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX

Cabin in Stanton

The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX
10.0 out of 10, Exceptional, (308)
"The shipping container was beautifully decorated and perfect size for our weekend getaway. The hot tub was great after hiking."
United States
Tara
The price is HK$1,322
HK$2,339 total
includes taxes & fees
28 Dec - 29 Dec
The WOODS Shipping Container Cabin-High Speed WiFi!-Hot Tub!-Covered Deck!-RELAX
Exterior
Hot Tub & WiFi - Romantic Hideaway

Cabin in Slade

Hot Tub & WiFi - Romantic Hideaway
9.0 out of 10, Wonderful, (88)
"This was the perfect spot for a getaway. Very clean, fast response from owner when needed. Definitely recommend for 2 people needing to unplug and relax. Hot tub was amazing. "
United States
Tiffany S.
The price is HK$1,018
HK$1,998 total
includes taxes & fees
28 Dec - 29 Dec
Hot Tub & WiFi - Romantic Hideaway
Living area
3 Miles Hollerwood/ATV Parking/Mountain Views

Cabin in Zoe

3 Miles Hollerwood/ATV Parking/Mountain Views
2.0 star property
The price is HK$470
HK$1,864 total
includes taxes & fees
8 Jan - 9 Jan 2026
3 Miles Hollerwood/ATV Parking/Mountain Views
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
"Great staff and facility. "
Nathan 1-night trip
Posted 2 days ago
Origin Lexington a Wyndham Hotel

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,782
Accommodation
260 Cabin Rentals
Lowest Price
HK$1,067
Highest Price
HK$2,810

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 HK$1,067 and HK$2,810 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 HK$1,067 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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