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Search the Best Cabins in Winchester

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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
$86 nightly
The price is $95
Dec 26 - Dec 27
Total with taxes and fees
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
$171 nightly
The price is $179
Dec 26 - Dec 27
Total with taxes and fees
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
$185 nightly
The price is $204
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$162 nightly
The price is $179
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$259 nightly
The price is $284
Jan 13 - Jan 14, 2026
Total with taxes and fees
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.
$177 nightly
The price is $195
Dec 24 - Dec 25
Total with taxes and fees
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.
$203 nightly
The price is $224
Jan 12 - Jan 13, 2026
Total with taxes and fees
"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.
$164 nightly
The price is $181
Jan 8 - Jan 9, 2026
Total with taxes and fees
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 traveler
$328 nightly
The price is $361
Jan 12 - Jan 13, 2026
Total with taxes and fees
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.
$193 nightly
The price is $214
Dec 25 - Dec 26
Total with taxes and fees
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.
$125 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$201 nightly
The price is $222
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$182 nightly
The price is $202
Jan 6 - Jan 7, 2026
Total with taxes and fees
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.
$171 nightly
The price is $187
Dec 28 - Dec 29
Total with taxes and fees
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
$236 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
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)
$287 nightly
The price is $315
Dec 24 - Dec 25
Total with taxes and fees
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.
$294 nightly
The price is $324
Dec 26 - Dec 27
Total with taxes and fees
"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.
$268 nightly
The price is $293
Dec 24 - Dec 25
Total with taxes and fees
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.
$252 nightly
The price is $280
Jan 8 - Jan 9, 2026
Total with taxes and fees
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
$217 nightly
The price is $240
Jan 8 - Jan 9, 2026
Total with taxes and fees
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

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"The staff member was so friendly! She even gave my kids some baggies with activities in them for them to do!"
Stephanie 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Lexington Green

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,700
Accommodation
260 Cabin Rentals
Lowest Price
$95
Highest Price
$361

Frequently asked questions

What are the best cabins near Winchester?
Ranging from small and basic to those that are all about luxury, there are 602 cabins available in and around Winchester. A few of the most popular options are 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 $95 and $361 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?
After spending your day having fun in Mother Nature, head home to the impeccable style and comfort of a Winchester luxury cabin. Cabin - Hot Tub, Wifi, No Pet Fee - Beary Cozy is a perfect option if you'd love to treat yourself. You'll appreciate the deluxe amenities here, such as a deck and a spa tub. 2 Bed Cabin Hot Tub - Fire Pit is another sought-after stay. Make use of a deck, a spa tub and a good deal more.
What are the best river cabins near Winchester?
Spend your days relaxing near the water and your nights listening to it surging past at a river cabin near Winchester. Our top recommendation — Hot Tub, Wifi, Adventure - New Family Cabin. This riverside getaway offers nearby ecotour services and a queen bed. Or, spend your break at Cabin - Pet - Friendly And Great Location. On top of its gorgeous location, amenities here include pet-friendly facilities and a deck.
What are the best cabins with pools near Winchester?
Slip on your swimsuit and go for a dip at your leisure when you book one of our cabin rentals with a pool. Cozy East Bernstadt Cabin With Porch + Fishing Lake is a winning option. A porch and a patio are among the other amenities that'll help make your stay comfortable. Or, enjoy some time out 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 your vacation in nature but don't feel like wrestling with tarpaulins and tent poles, a cabin is the way to go. Book a few nights or longer at Cabin - Sits On 8 Private Acres, Hiking Trails At This Secluded Chalet Wi. This favorite comes with an oven, a stovetop and more. You can also experience comfort and outdoor fun in the perfect package at Cave Run Red River Gorge Cabin. A firepit and a garden are among this retreat's 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. Ditch the office cubicle for a few days in the great outdoors at Cabin - Private, Gated, Wall Of Windows. On-site watersports and a firepit are some amenities it comes with. Otherwise, forget all about work at Whispering Pine Cabin Unit 2 In The Rrg. Kick back here and take advantage of 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 $95 per night.
Can I find log cabins in Winchester?
Kick off your day with a hot coffee in your log cabin and then spend the rest of your time fishing and picnicking. Sound like your dream vacation? Then head for Big Rock Log Cabin, Beside Natural Bridge. Another wooden retreat that comes with ample charm and warmth is Hot Tub, Wifi, Adventure - Family Log Cabin. Activities like fishing and hiking will add to your memories here.
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 travelers. It offers amenities like a patio and a firepit. Cozy Secluded Cabin With Wi - Fi is another fabulous option. Quality conveniences such as a porch and a patio will help make your stay a comfortable one.
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 nature-filled escape that won't cost a fortune, you can't beat a cabin. Visualize yourself waking up to the sounds of wildlife and sipping coffee on a private deck surrounded by stunning vistas. Stay in a cabin in Winchester to get away from the fast pace of modern life. Whether they're beachside, lakeside or up a mountain, cabins offer a uniquely relaxing experience for anyone needing a break.
What are the top nature cabins in Winchester?
Make a booking at Hot Tub, Wifi, Adventure - New Family Cabin and let all your troubles float downstream. Fun activities like nearby golfing and nearby fishing help make this river cabin in Winchester a top option. Cabin - Pet - Friendly And Great Location is another property where you can relax in nature. If you're in the mood for adventure, go nearby horse riding and hiking.
What are some of the best cabins near Bluegrass Heritage Museum in Winchester?
Secluded Getaway In Beautiful New Cabin Near Red River Gorge is popular cabin in Bluegrass Heritage Museum. Home comforts, a picture-perfect backdrop and access to activities such as nearby hiking and biking trails and nearby rock climbing help make it the ideal escape. Hot Tub, Wifi, Pet - Friendly - Cozy Tiny Cabin also combines nature and adventure. Spend your stay here and add nearby fishing and nearby kayaking to your to-do list.

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