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Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Cabin Rentals in Winchester and around

Property grounds
Eco-Chic Retreat in Kentucky, Perfect for Glamping in Style near Red River Gorge

Eco-Chic Retreat in Kentucky, Perfect for Glamping in Style near Red River Gorge

Stanton
The price is €130
includes taxes & fees
8 Dec - 9 Dec
Eco-Chic Retreat in Kentucky, Perfect for Glamping in Style near Red River Gorge
Exterior
Ultimate Glamping Getaway near Red River Gorge, Kentucky, Perfect for Romantic Getaways

Ultimate Glamping Getaway near Red River Gorge, Kentucky, Perfect for Romantic Getaways

Stanton
The price is €130
includes taxes & fees
8 Dec - 9 Dec
Ultimate Glamping Getaway near Red River Gorge, Kentucky, Perfect for Romantic Getaways
Property grounds
Secluded A-Frame Cabin in Stanton, Kentucky - Perfect Glamping Spot near Red River Gorge

Secluded A-Frame Cabin in Stanton, Kentucky - Perfect Glamping Spot near Red River Gorge

Stanton
The price is €130
includes taxes & fees
8 Dec - 9 Dec
Secluded A-Frame Cabin in Stanton, Kentucky - Perfect Glamping Spot near Red River Gorge
Exterior detail
Glamping Retreat for the Modern Explorer in this Lovely A-Frame Rental in Kentucky

Glamping Retreat for the Modern Explorer in this Lovely A-Frame Rental in Kentucky

Stanton
The price is €130
includes taxes & fees
8 Dec - 9 Dec
Glamping Retreat for the Modern Explorer in this Lovely A-Frame Rental in Kentucky
View from room
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 star property
Slade
8.6 out of 10, Excellent, (1764)
"Beautiful autumn stay."
United States
Cheryl
Natural Bridge State Resort Park
Microwave, oven, stovetop
NEW, Promo Pricing - Karmic Loft Woodland Escape

NEW, Promo Pricing - Karmic Loft Woodland Escape

Stanton
9.4 out of 10, Exceptional, (3)
"We wanted to try out a tiny house. This met the mark, it was small but accommodating. I wish we had a head up that the toilet was a composting toilet not plumbed. If you are looking for a complete shut down weekend, this is the place no cell signal or Wi-Fi. We enjoyed the peacefulness. "
United States
Breeze B.
The price is €202
includes taxes & fees
9 Nov - 10 Nov
NEW, Promo Pricing - Karmic Loft Woodland Escape
Exterior
Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge

2.0 star property
Stanton
10.0 out of 10, Exceptional, (4)
"The property was in good condition. Everything was clean. The area was quiet. The driveway could use some smoothing out but we had a nice stay."
United States
Monica
The price is €237
includes taxes & fees
6 Dec - 7 Dec
Dappled Grey Cabin with hot tub at Red River Gorge
Exterior
New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin

2.0 star property
Jeffersonville
10.0 out of 10, Exceptional, (2)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is €167
includes taxes & fees
11 Nov - 12 Nov
New, Cozy, Secluded Cabin
Exterior
Backcountry Shelter | 0 Bed, 0.5 Bath

Backcountry Shelter | 0 Bed, 0.5 Bath

Stanton
8.8 out of 10, Excellent, (6)
"The little cabin was almost exactly as described. It's in a beautiful area and has a trail out back that goes through some great scenery. The only things that were different from the listing were 1) no sheets or adequate blanket on the second bed, just a thin blanket covering the mattress and 2) no running water when we went in mid November. I think they shut off the water earlier in the year. They did provide two large jugs of water in those large blue containers, so we were able to drink from...
United States
Sarah M.
Backcountry Shelter | 0 Bed, 0.5 Bath
Exterior
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

Frenchburg
9.8 out of 10, Exceptional, (15)
"Place is absolutely beautiful! We absolutely loved it!would absolutely stay again"
United States
John M.
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
Exterior
240 Sq Ft Tiny Home w/ WIFI in Irvine

240 Sq Ft Tiny Home w/ WIFI in Irvine

Irvine
10.0 out of 10, Exceptional, (9)
"We love our vacations simple and this place made just that happen! Close enough to get to places to see yet far enough away for perfect privacy! We really enjoyed our stay! "
United States
Samantha M.
The price is €188
includes taxes & fees
8 Dec - 9 Dec
240 Sq Ft Tiny Home w/ WIFI in Irvine
Exterior detail
"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin

Stanton
9.0 out of 10, Wonderful, (12)
"The property was everything it was booked to be. Perfect location, right in the middle of everything, but still very private!!"
United States
Walter M.
"Rocky Top" - Cozy RRG Cabin
Exterior
"Black Hawk" - Overlook Cabin in RRG

"Black Hawk" - Overlook Cabin in RRG

Stanton
10.0 out of 10, Exceptional, (2)
"It was a beautiful, well kept little two-story cabin with two big wrap around porches. There were two nice fire pit outdoor areas. The accommodations were very clean and the bed was comfortable."
United States
Mark S.
"Black Hawk" - Overlook Cabin in RRG
Exterior
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

2.0 star property
Stanton
9.8 out of 10, Exceptional, (14)
"Easy access into the house. All information was provided by our host. Home has everything you need, it was clean and beds are comfortable. Restaurants close by and enjoyed our stay. We will definitely do this again "
United States
Leanne
The price is €312
includes taxes & fees
19 Nov - 20 Nov
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Exterior
Tranquil Getaway in the Woods ~ Sunset Ridge

Tranquil Getaway in the Woods ~ Sunset Ridge

Irvine
10.0 out of 10, Exceptional, (78)
"The stay was awesome! My husband asked if we could stay another night. It is so quiet and peaceful here. Awesome experience!"
United States
Marsha
The price is €132
includes taxes & fees
9 Nov - 10 Nov
Tranquil Getaway in the Woods ~ Sunset Ridge
Exterior
"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG

Stanton
10.0 out of 10, Exceptional, (4)
"Impressive views and overall a great mountain escape "
United States
Justin M.
"Cardinal Crest" - Overlook Dome 002 in RRG
Exterior
Mountain Memories Cabin

Mountain Memories Cabin

Stanton
10.0 out of 10, Exceptional, (58)
"We had a wonderful stay! Clean, safe and excellent hospitality! "
United States
Matthew K.
The price is €173
includes taxes & fees
9 Nov - 10 Nov
Mountain Memories Cabin
Exterior
Cozy Cabin in Red River Gorge

Cozy Cabin in Red River Gorge

Jeffersonville
10.0 out of 10, Exceptional, (3)
"Wonderful cabin. Very comfortable, quiet location."
United States
Linda S.
Cozy Cabin in Red River Gorge
Exterior
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

Stanton
9.4 out of 10, Exceptional, (54)
"We thoroughly enjoyed our stay at this cabin. It was clean and had well-furnished kitchen. The hot tub is a nice addition to soothe sore muscles after hiking. We saw an indigo bunting, deer and fawn, and group of turkeys with young."
United States
Jennifer M.
The price is €270
includes taxes & fees
29 Nov - 30 Nov
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge
Exterior
Perfect Perch at Three Suns Cabins

Perfect Perch at Three Suns Cabins

Stanton
10.0 out of 10, Exceptional, (3)
"The cabin was very clean and it had the perfect amount of space. We loved the grounds with the walking trails. "
United States
Sarah P.
Perfect Perch at Three Suns Cabins
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

Hilton Lexington/Downtown

Hilton Lexington/Downtown

10/10 Excellent
"Clean comfortable room"
Marian 1-night trip
Posted 2 days ago
Hilton Lexington/Downtown

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,000
Accommodation
253 Cabin Rentals
Lowest Price
€127
Highest Price
€312

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 €127 and €312 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 €127 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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