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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

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 €158
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 €177
includes taxes & fees
6 Jan - 7 Jan 2026
Quaint, heavily forested cabin, mountain valley view.
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 €156
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub! Tiny Cabin Retreat near RRG
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 €306
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
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 €170
includes taxes & fees
24 Dec - 25 Dec
Mountain Memories 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 €193
includes taxes & fees
12 Jan - 13 Jan 2026
"Rocky Top" - Cozy RRG Cabin
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 €158
includes taxes & fees
22 Jan - 23 Jan 2026
Hot Tub! Tiny House Retreat in the Woods
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 €317
includes taxes & fees
5 Jan - 6 Jan 2026
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
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 €187
includes taxes & fees
25 Dec - 26 Dec
A Frame of Mind - near Red River Gorge KY
Exterior
Tranquil Getaway in the Woods ~ Sunset Ridge

Cabin in Irvine

Tranquil Getaway in the Woods ~ Sunset Ridge
10.0 out of 10, Exceptional, (83)
"Beautiful, secluded and spacious "
United States
Shannon H.
The price is €121
includes taxes & fees
4 Jan - 5 Jan 2026
Tranquil Getaway in the Woods ~ Sunset Ridge
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 €205
includes taxes & fees
22 Jan - 23 Jan 2026
NEW, Promo Pricing - Karmic Loft Woodland Escape
Exterior
Hot Tub & WiFi - Cozy Canopy - Red River Gorge KY

Cabin in Stanton

Hot Tub & WiFi - Cozy Canopy - Red River Gorge KY
9.6 out of 10, Exceptional, (310)
"Cabin was wonderful. Great communication before and during arrival and was so incredibly clean. Definitely recommend!"
United States
Todd
The price is €177
includes taxes & fees
6 Jan - 7 Jan 2026
Hot Tub & WiFi - Cozy Canopy - Red River Gorge KY
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 €162
includes taxes & fees
6 Jan - 7 Jan 2026
New, Cozy, Secluded Cabin
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 €229
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub, WiFi & Pet-Friendly - Pilot Point
Exterior
Stargazer Cabin-Look Up. Relax. Repeat.

Cabin in Irvine

Stargazer Cabin-Look Up. Relax. Repeat.
9.8 out of 10, Exceptional, (9)
The price is €276
includes taxes & fees
24 Dec - 25 Dec
Stargazer Cabin-Look Up. Relax. Repeat.
Exterior
"Cardinal Crest" - Overlook Dome 002 in RRG

Cabin in Stanton

"Cardinal Crest" - Overlook Dome 002 in RRG
10.0 out of 10, Exceptional, (4)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
"Cardinal Crest" - Overlook Dome 002 in RRG
Exterior
Turkey Cove: Newly Renovated, Pet-Friendly 3BR Home with Hot Tub and Fireplace

Cabin in Stanton

Turkey Cove: Newly Renovated, Pet-Friendly 3BR Home with Hot Tub and Fireplace
9.0 out of 10, Wonderful, (44)
"Cozy cabin with updated amenities and a great hot tub!"
United States
Nicole S.
The price is €258
includes taxes & fees
24 Dec - 25 Dec
Turkey Cove: Newly Renovated, Pet-Friendly 3BR Home with Hot Tub and Fireplace
Exterior
Hot Tub, WiFi, Pet-Friendly - Mountain Spirit

Cabin in Stanton

Hot Tub, WiFi, Pet-Friendly - Mountain Spirit
9.2 out of 10, Wonderful, (110)
"This place had great views, was very clean and would definitely stay here again! "
United States
Tracy Z.
The price is €244
includes taxes & fees
8 Jan - 9 Jan 2026
Hot Tub, WiFi, Pet-Friendly - Mountain Spirit
Living area
3 Miles Hollerwood/ATV Parking/Mountain Views

Cabin in Zoe

3 Miles Hollerwood/ATV Parking/Mountain Views
2.0 star property
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"The room was very nice and the staff was also!"
Crystal 1-night trip
Posted 1 day ago
Hyatt Regency Lexington

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,700
Accommodation
232 Cabin Rentals
Lowest Price
€121
Highest Price
€317

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 €121 and €317 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 €121 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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