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Featured Cabin Rentals in Winchester

Fridge, microwave, oven, stovetop
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
10.0 out of 10, Exceptional, (248)
"First off, we would go out of our way to stay here again. The property was beautiful and the pictures of the cabin do not do it justice. The property owner was very easy to communicate with and responded quickly when you send a message. The cabin and property were immaculately clean and ammenities were very well kept.This has been added as a must stay next time we are in the area."
The price is NZ$401
per night
22 May - 23 May
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
Pool
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (96)
"We loved how secluded it was, but close to the park and restaurants. The hot tub and fire pit were a nice addition. It was well decorated and felt upscale. I liked that it had k-cups. Love the travel pics on the wall. We had a great time and enjoyed the accommodations. Overall a wonderful get away. We will definitely be back!"
The price is NZ$348
per night
15 May - 16 May
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Exterior
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
10.0 out of 10, Exceptional, (232)
"It’s it’s was a beautiful and unique cabin. Very clean, easy check in, and loved the area. 10/ 10 would recommend for couples or just a home base for the red river gorge."
The price is NZ$377
per night
20 May - 21 May
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
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Outdoor spa tub
Shipping Container Den-Hot Tub!-View! FREE FIREWOOD for May weeknight bookings!
10.0 out of 10, Exceptional, (50)
"We had a blast at this property. It’s perfect for a two person stay."
The price is NZ$390
per night
15 May - 16 May
Shipping Container Den-Hot Tub!-View! FREE FIREWOOD for May weeknight bookings!
Interior
NEW CONSTRUCTION 2BR cabin near Red River Gorge, FRENCHBURG, Montgomery County
10.0 out of 10, Exceptional, (9)
"We had a wonderful time staying here for a romantic weekend getaway. The cabin is very cute, cozy and clean. It is in a quiet and peaceful setting with an amazing view. We loved sitting out on the deck in the morning drinking our coffee while enjoying the view and the sounds of nature. I would highly recommend staying here."
NEW CONSTRUCTION 2BR cabin near Red River Gorge, FRENCHBURG, Montgomery County
Exterior
Amazing Views! Hot Tub!! Minutes from the Gorge!!!
10.0 out of 10, Exceptional, (11)
"Nice place to relax! The view is awesome and just minutes away from the Red Rver Gorge. Definitely would recommend!"
Amazing Views! Hot Tub!! Minutes from the Gorge!!!
Property grounds
Secluded getaway in beautiful new cabin near Red River Gorge.
10.0 out of 10, Exceptional, (50)
"The cabin and location are amazing! Definitely plan to come back!"
The price is NZ$416
per night
15 May - 16 May
Secluded getaway in beautiful new cabin near Red River Gorge.
Exterior
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
10.0 out of 10, Exceptional, (14)
"Very peaceful and quite. We enjoyed sitting outside on the porch! A nice place to stay."
The price is NZ$297
per night
19 May - 20 May
Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Living area
Barred Owl Cabin. Hand-Hewn Log Cabin behind the Nada Tunnel.
10.0 out of 10, Exceptional, (6)
"The cabin was in a great location. The drive up to the cabin was a bit of a challenge. Definitely need a four wheel or awd vehicle. Quiet evenings. Due to a foot injury, we ended up staying at the cabin throughout the day and evening. So we got a chance to enjoy the tranquility of the area. The furnishings were great. We were surprised by the number of electrical outlets which was plentiful and strategic. I would recommend the cabin as a great getaway spot."
The price is NZ$434
per night
15 May - 16 May
Barred Owl Cabin. Hand-Hewn Log Cabin behind the Nada Tunnel.
Fridge, microwave, oven, stovetop
Moondance Cabin near Red River Gorge - Hot Tub
10.0 out of 10, Exceptional, (41)
"We are two couples that love to hike and enjoy cabin life which we did here for a seven night stay. The cabin is pretty new, with quality construction and furnishings. We found the cabin very clean, with everything we needed and everything works. We cooked two meals a day and ate inside or out on the porch where we could enjoy the view and listen to the birds. The hot tub was very welcome after a day of hiking. We had a great week!"
Moondance Cabin near Red River Gorge - Hot Tub
Fridge, oven, stovetop, coffee/tea maker
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (240)
"Great little cabin in the woods. Pretty much as advertised. The beds were not good. Very mushy and soft. My chiropractor will have fun with me at our next appointment."
The price is NZ$406
per night
11 Jun - 12 Jun
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Property grounds
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (116)
"Nice property"
The price is NZ$399
per night
6 Jun - 7 Jun
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Exterior
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (37)
"The ants were bad, but we bought oranges and used the peels. Also, the stove only worked with the skillets. We improvised and it was a really nice getaway"
The price is NZ$344
per night
15 May - 16 May
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Exterior
Wildcat Cabin | RRG | Hot tub
9.6 out of 10, Exceptional, (8)
"Perfect little cabin close to everything"
Wildcat Cabin | RRG | Hot tub
Smart TV, fireplace, books
1800’s Historical Log Cabin near I-75 Interstate
9.6 out of 10, Exceptional, (5)
"Met our expectations as shown on the VRBO site. Spent the week visiting with friends, a day at Keenland, and of course a few distilleries."
The price is NZ$341
per night
15 May - 16 May
1800’s Historical Log Cabin near I-75 Interstate
Interior
Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!
9.4 out of 10, Exceptional, (32)
"We had an absolute amazing time. A beautiful cabin with a beautiful view. Management was amazing and got right back to me when we needed something. We will be staying again."
The price is NZ$446
per night
21 May - 22 May
Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!
1 bedroom, WiFi, bed sheets
Mountain Memories | RRG |
9.4 out of 10, Exceptional, (11)
"We had a great time and stay at the cabin. Was located 15 mins away from attractions and restaurants. Only thing was the gravel road to the cabin was something we werent expected. Needs a ceiling fan in order to circulate the air around from the upstairs. Great outdoor view on the balcony to have breakfast and dinner. Miguels pizza was great pizza spot. Had fun hiking to the natiral bridge."
Mountain Memories | RRG |
Exterior
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
9.4 out of 10, Exceptional, (51)
"My boyfriend and I stayed there for three night's and 4 days. The place was perfectly located by both the parks and close to everything we needed. However, getting up to the cabin was an adventure of itself as it's located up pretty high with steep hills and sharp turns, so being a confident/comfortable driver is a must. The cabin was very neat and clean and included everything we needed for our stay, even a coffee and popcorn maker. My only complaint was that the stairs matched the steep hill...
The price is NZ$442
per night
28 May - 29 May
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Property grounds
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Sundance - Red River Gorge, Kentucky!
9.4 out of 10, Exceptional, (104)
"Nice stay away with friends for a girls weekend!"
The price is NZ$476
per night
15 May - 16 May
Hot Tub, WiFi, Pet-Friendly - Family Cabin - Sundance - Red River Gorge, Kentucky!
Fridge, microwave, stovetop, coffee/tea maker
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
9.4 out of 10, Exceptional, (6)
"We enjoyed our stay at this home to visit with family and attend Court Days. The house was great for seven of us, lots of room. The only issue we had was the falling black walnuts all over the driveway and steps. We had to park the cars out of the way so not under the falling black walnuts to prevent damage. The grounds looked great, but we had rain all weekend so could not enjoy the firepit. Thanks for a great KY weekend!"
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
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See all available properties in Winchester
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.

Other property types in Winchester

Pool
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (96)
"We loved how secluded it was, but close to the park and restaurants. The hot tub and fire pit were a nice addition. It was well decorated and felt upscale. I liked that it had k-cups. Love the travel pics on the wall. We had a great time and enjoyed the accommodations. Overall a wonderful get away. We will definitely be back!"
The price is NZ$348
per night
15 May - 16 May
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Fridge, microwave, oven, stovetop
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
10.0 out of 10, Exceptional, (248)
"First off, we would go out of our way to stay here again. The property was beautiful and the pictures of the cabin do not do it justice. The property owner was very easy to communicate with and responded quickly when you send a message. The cabin and property were immaculately clean and ammenities were very well kept.This has been added as a must stay next time we are in the area."
The price is NZ$401
per night
22 May - 23 May
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
Fridge, oven, stovetop, coffee/tea maker
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (240)
"Great little cabin in the woods. Pretty much as advertised. The beds were not good. Very mushy and soft. My chiropractor will have fun with me at our next appointment."
The price is NZ$406
per night
11 Jun - 12 Jun
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
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.

Winchester Cabin Rentals information

Number of reviews
1,458
Accommodation
155 Cabin Rentals
Lowest Price
NZ$294
Highest Price
NZ$476

Frequently asked questions

What are the best cabins near Winchester?
Ranging from small and quaint to those full of luxury and style, there are 293 cabins available in and around Winchester. Some of our most popular options include Secluded Red River Gorge Pet - Friendly Cabin On 3 Acres - Serenity Falls and Maco’s Mountain Resort - Hemlock Cabin.
Are there cheap cabins in Winchester?
For a budget-friendly escape in the great outdoors, take a look at our cheap cabins in Winchester. Wake in the mornings to the sound of birds singing from one of our cosy stays priced from NZ$294 to NZ$476 a night.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?
Splash out and book a holiday you’ll never forget at one of our Winchester luxury cabins. Hot Tub, Wifi - Woodsman - Rugged Rustic Cabin is one option where you can spend a couple of days or so appreciating the finer things. It features a spa tub and a firepit. Or, use Hot Tub, Wifi - Family Cabin - Wine Cellar as a base to explore the beautiful natural areas around you. Nice touches here include a deck and a king bed.
What are the best river cabins near Winchester?
If you’re looking for a comfortable retreat overlooking the water, a Winchester river cabin is hard to go past. Settle in at Newly - Built See Rocks Vista Cabin and let all your stresses disappear downstream. Amenities here include nearby wildlife walks and nearby birdwatching activities. Another quality riverside option is Cabin - Hot Tub, Wifi, Pet - Friendly - Beary Cosy. You’ll have use of nearby wildlife walks, nearby birdwatching activities and more.
What are the best cabins with pools near Winchester?
Put on your swimsuit and enjoy a refreshing dip whenever the mood strikes when you reserve one of our cabin homes with a pool near Winchester. Cabin - Serene, Beautiful Views With Hot Tub is a top choice. A swimming pool and a patio are some other amenities that await you here. Or, spend your getaway at Hot Tub, Wifi - Family Cabin - Wine Cellar. As well as a pool, this cabin comes with a porch and a spa tub.
What are some great Winchester cabins?
When you want to spend time with Mother Nature but don’t feel like wrestling with tarpaulins and tent poles, a cabin is an excellent choice. Book a few nights or more at Cabin - Bourbon Trail, Ark Encounter, Family Gatherings. This visitor favourite comes with a nearby waterfront, a firepit and more. Alternatively, experience outdoor fun and comfort combined at Luxurious Cabin Across From The Red River Gorge. A fireplace and a firepit are among the amenities here.
What are the best weekend cabin homes in Winchester?
If you’d love to spend a few glorious days surrounded by nature, Cabin - Bourbon Trail, Ark Encounter, Family Gatherings is just the place. Get comfy here for a weekend and make use of conveniences including windsurfing and a spa tub. Another superb retreat is Luxurious Cabin Across From The Red River Gorge. Offering windsurfing, a fireplace and plenty of chill vibes, you’ll go home feeling refreshed and renewed.
What are the best cabin prices in Winchester?
With prices starting from as little as NZ$294 a night for a cabin home in Winchester, there’s no reason to rough it in a tent.This price was 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.
Can I find log cabins in Winchester?
If you’re looking for a more laid-back pace, you’ll find it at one of our log cabins in Winchester. For example, Well Decorated Log Cabin, Themed In Red And Black rooster Furnishings. Spend your days here caving and shore fishing and then return home to relax among its many comforts. Time also seems to go slower at Secluded Log Cabin In A Heavily Forested Area. When you want to venture beyond your front door, hiking and fishing opportunities are close by.
What are the highest-rated cabins in Winchester?
Expedia travellers keep going back to Cabin - Bourbon Trail, Ark Encounter, Family Gatherings. This hot spot comes with a host of amenities including windsurfing and a spa tub. It’s not difficult to understand why Luxurious Cabin Across From The Red River Gorge is also popular with visitors. Conveniences like windsurfing and a fireplace will help make your stay nice and comfortable.
What are the top things to see and do in Winchester?
Any fabulous cabin stay should involve checking out some sights. For example, Bluegrass Heritage Museum. It’s one of the leading attractions in Winchester. If you’d like to explore a little farther out, rent a car and head to Cassell Creek Golf Course.
Why should I book a cabin in Winchester?
For a nature-filled holiday that won’t blow your budget, you can’t beat a cabin. Imagine rising to the sounds of the wilderness and drinking coffee on a private deck surrounded by dreamy views. Lock in a cabin in Winchester and say goodbye to the hectic routine of modern life. Whether they’re in the mountains, by the beach or someplace else, cabins offer an affordable and relaxing experience for those who need a break.

Recent Reviews in Winchester
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