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Compare 181 Cabin Rentals in Winchester with updated reviews, rates, and availability.

Natural Bridge State Resort Park
Outdoor pool
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1325)
"Beautiful views. Property could use a finish refresh but the beds are comfortable and staff are friendly. Would stay again."
The price is $131
$144 total
includes taxes & fees
Jun 9 - Jun 10
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Fridge, oven, stovetop, coffee/tea maker
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (242)
"The cabin was amazing. Nice and peaceful location. The cabin had everything that we needed. The jacuzzi was nice and relaxing, My wife enjoyed it very much! We are planning to get one at home shortly. The location of the property was a little puzzling at first. When we started to venture of and visit locations. The placement of the property made perfect sense! You’re literally right in the middle of everything that you will want to see! Everything interesting is just a few miles away! My wife...
The price is $172
$294 total
includes taxes & fees
Jul 7 - Jul 8
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Pool
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (99)
"This was a great property that was exactly the way it was described in VRBO. Would definitely stay here again!"
The price is $129
$225 total
includes taxes & fees
Jun 9 - Jun 10
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
Outdoor spa tub
The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
10.0 out of 10, Exceptional, (56)
"The property was very clean and interesting to stay in. The hot tub was much appreciated after long days of hiking. Had a great time."
The price is $139
$237 total
includes taxes & fees
Jun 9 - Jun 10
The Container Den-Shipping Container Cabin with HotTub-WIFI-Great View! BOOK IT!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near 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, (39)
"After both of us working super hard in 2024 non stop, we needed a quiet little getaway from society. This was perfect! We put our phones away for a few days and just spent quality time together! I highly recommend this cabin for anyone looking to take a break from the real world! Lol"
The price is $105
$212 total
includes taxes & fees
Jun 11 - Jun 12
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Interior
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
8.8 out of 10, Excellent, (32)
"Could use some updating and tlc. Wasnt a issue but there was only enough seat place for 3 people to watch tv. All in all it was fine and we enjoyed our stay."
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
Property grounds
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
9.2 out of 10, Wonderful, (130)
"Fun relaxing cabin in the woods"
The price is $153
$289 total
includes taxes & fees
Jun 12 - Jun 13
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
Red River Gorge Birch Hollow Hideaway
Living area
Red River Gorge Birch Hollow Hideaway
10.0 out of 10, Exceptional, (6)
"The cabin was wonderful we had a great time is was very beautiful and everything that was advertised we give it 5 stars"
The price is $130
$165 total
includes taxes & fees
Jun 12 - Jun 13
Red River Gorge Birch Hollow Hideaway
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - 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, (118)
"The cabin was perfect for our stay to go hiking in Red River Gorge and Natural Bridge. The cabin had everything that you need for a comfortable and enjoyable trip. We loved the hot tub after hiking all day and the seclusion of the cabin was delightful. It was very peaceful for us. I would recommend this cabin for a great stay in Kentucky."
The price is $122
$245 total
includes taxes & fees
Jun 11 - Jun 12
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
Exterior
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
10.0 out of 10, Exceptional, (237)
"We were amazed at how clean and neat and relaxing this place was! Absolutely 5 star worthy! It was like living in a tree house - sitting on the covered porch with our morning tea, listening to the birds. We would highly recommend this place - Amanda and Chad are wonderful hosts and when we lost power due to storm, they even offered to bring us coffee. Make reservations today - you won’t regret it!"
The price is $139
$255 total
includes taxes & fees
Jun 26 - Jun 27
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
Fridge, microwave, oven, stovetop
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
10.0 out of 10, Exceptional, (252)
"We needed a relaxing weekend and this property was perfect. The container concept was well executed, property kept very clean, and we are already talking about when to come back for a longer stay."
The price is $139
$254 total
includes taxes & fees
Jun 12 - Jun 13
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Interior
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
8.2 out of 10, Very Good, (91)
"Loved the secluded area and the cabin was lovely"
The price is $115
$225 total
includes taxes & fees
Jun 10 - Jun 11
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Hot Tub & No Pet Fee - Beary Secluded - Small Family Cabin in Red River Gorge, Kentucky!
Interior
Hot Tub & No Pet Fee - Beary Secluded - Small Family Cabin in Red River Gorge, Kentucky!
9.0 out of 10, Wonderful, (73)
"Overall great time. The location was perfect for our purposes. The inside was clean and neat. The furniture was a little worn and broken down. The bedroom lights didn’t have shades, so the bare bulbs were harsh. The finishes in the bathroom were poorly done."
The price is $184
$317 total
includes taxes & fees
Jul 2 - Jul 3
Hot Tub & No Pet Fee - Beary Secluded - Small Family Cabin in Red River Gorge, Kentucky!
Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View
Property grounds
Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View
10.0 out of 10, Exceptional, (33)
"Even before booking, Mr. Brad was so great and prompt answering questions! The place was immaculate and the pictures do not do it justice! You will love it here! Quiet neighborhood, about 30 minutes away from the hustle and bustle, which was what we were looking for."
The price is $175
$335 total
includes taxes & fees
Jun 9 - Jun 10
Starway to Heaven Cabin at Red River Gorge - Hot Tub - Great View
Wildwood Cabin RRG, Hot tub-private hikes nearby
TV, fireplace
Wildwood Cabin RRG, Hot tub-private hikes nearby
9.4 out of 10, Exceptional, (3)
"We went to the cabin for the first three days of our honeymoon. We enjoyed the private hikes up and around the rocky bluff. The rocks offered moderate difficulty for beginner rock climbers and a great view from the higher ledges. There is a neighbor cabin in direct eye shot of the cabin, but we had fun there."
Wildwood Cabin RRG, Hot tub-private hikes nearby
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Property grounds
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (105)
"We had a wonderful time. The cabin was clean and comfortable. It is close to a lot of great hiking trails. There’s a grocery store, several restaurants, and gas stations all close by. Would definitely stay here again!"
The price is $155
$285 total
includes taxes & fees
Jun 13 - Jun 14
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Cozy Red River Gorge Cabin w/Hot Tub & Fire Pit
Property grounds
Cozy Red River Gorge Cabin w/Hot Tub & Fire Pit
10.0 out of 10, Exceptional, (14)
"Cozy little cabin with all the comforts of home on a ridge overlooking a beautiful wooded valley. The hot tub on the deck was wonderful!"
Cozy Red River Gorge Cabin w/Hot Tub & Fire Pit
Nestled in the beautiful mountains of the Red River Gorge Area
Exterior
Nestled in the beautiful mountains of the Red River Gorge Area
8.0 out of 10, Very Good, (1)
"The cabin was clean enough except for the linens that smelled of cigarette smoke. We had a problem with check-in due to not receiving an entry code from VRBO. With no cell service, we had to drive to find reception to call the Scenic Cabin rentals for our code. Fortunately, we arrived during daylight hours."
Nestled in the beautiful mountains of the Red River Gorge Area
Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!
TV, fireplace
Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!
8.8 out of 10, Excellent, (73)
"Great location, close to restaurants and state park."
The price is $156
$276 total
includes taxes & fees
Jun 10 - Jun 11
Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!
Eagle View RRG -Hot Tub-spacious!
Property grounds
Eagle View RRG -Hot Tub-spacious!
9.4 out of 10, Exceptional, (6)
"Fantastic property with great amenities. Would definitely stay here again!"
Eagle View RRG -Hot Tub-spacious!
Don't see what you're looking for?
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

Natural Bridge State Resort Park
Outdoor pool
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1325)
"Beautiful views. Property could use a finish refresh but the beds are comfortable and staff are friendly. Would stay again."
The price is $131
$144 total
includes taxes & fees
Jun 9 - Jun 10
Natural Bridge State Resort Park
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Fridge, oven, stovetop, coffee/tea maker
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (242)
"The cabin was amazing. Nice and peaceful location. The cabin had everything that we needed. The jacuzzi was nice and relaxing, My wife enjoyed it very much! We are planning to get one at home shortly. The location of the property was a little puzzling at first. When we started to venture of and visit locations. The placement of the property made perfect sense! You’re literally right in the middle of everything that you will want to see! Everything interesting is just a few miles away! My wife...
The price is $172
$294 total
includes taxes & fees
Jul 7 - Jul 8
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Pool
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (99)
"This was a great property that was exactly the way it was described in VRBO. Would definitely stay here again!"
The price is $129
$225 total
includes taxes & fees
Jun 9 - Jun 10
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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
2,926
Accommodation
181 Cabin Rentals
Lowest Price
$105
Highest Price
$184

Frequently asked questions

What are the best cabins near Winchester?
Experience the great outdoors without giving up the comforts at one of our 475 cabins in and around Winchester. Whether you have relaxation or fun on your itinerary, Secluded Red River Gorge Pet - Friendly Cabin On 3 Acres - Serenity Falls has plenty of both. Alternatively, get cozy at Maco’s Mountain Resort - Hemlock Cabin and enjoy its beautiful natural surroundings.
Are there cheap cabins in Winchester?
Priced between $105 and $184 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, return home to the serious comfort and style of a Winchester luxury cabin. Cabin - Hot Tub, Wifi, Pet - Friendly - Beary Cozy is an excellent option if you’d love to enjoy the finer things. You’ll enjoy the deluxe amenities here, such as a deck and a spa tub. Cabin - Muirs Retreat Rrg - Hot Tub - No Cleaning Fee is another appealing stay. Make use of a spa tub, off-street parking options and a whole lot more.
What are the best river cabins near Winchester?
Spend your days making the most of the water and your evenings listening to it rolling past at a river cabin near Winchester. Our top pick — 4500 Sq Ft Secluded Log Cabin Home. This riverside escape offers nearby birdwatching activities and a firepit. Alternatively, throw your bags down at Upscale Shipping Container Cabin In The Woods Of Red River Gorge. Along with its lovely location, highlights here include outdoor furniture and nearby birdwatching activities.
What are the best cabins with pools near Winchester?
If you love the idea of every day being a pool day, make a reservation at Cabin - Serene, Beautiful Views With Hot Tub. It’s one of our top recommended cabin rentals with a pool and comes with useful amenities like a swimming pool and a spa tub. Cabin With Wi - Fi is another great place to spend lazy days poolside. A barbecue grill, a swimming pool and good times are all on the menu here.
What are some great Winchester cabins?
Tucked away in nature but with plenty of creature comforts, nothing tops a cabin if you’d love to really experience the great outdoors. Cabin - Bourbon Trail, Ark Encounter, Family Gatherings is a wonderful place to escape from the daily grind. Amenities here include nearby museums and a king bed. Luxurious Cabin Across From The Red River Gorge is another sought-after property. A king bed and a firepit will help make your visit nice and comfy.
What are the best weekend cabin rentals in Winchester?
It doesn’t get much better than a weekend cabin getaway after an exhausting week at work. Swap the office for a few days or more in nature at Cabin - Bourbon Trail, Ark Encounter, Family Gatherings. A patio and a firepit are a few of the amenities it offers. You can also forget all about work at Luxurious Cabin Across From The Red River Gorge. Settle in here and make the most 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 $105 per night.
Can I find log cabins in Winchester?
For some adventurers, the ideal outdoor vacation is all about staying in a cozy log cabin. Go adventuring or simply unwind and relax at Well Decorated Log Cabin, Themed In Red And Black rooster Furnishings. Recreational activities such as canoeing and camping are among the fun things to do here. Another enticing log cabin getaway is Secluded Log Cabin In A Heavily Forested Area. Quad biking and shore fishing will keep you on the go when you’re not chilling in your timber-clad digs.
What are the highest-rated cabins in Winchester?
Guests keep going back to Cabin - Bourbon Trail, Ark Encounter, Family Gatherings. This hot spot comes with plenty of handy amenities like a patio and a firepit. It won’t take you much time to see why Luxurious Cabin Across From The Red River Gorge is also a hit with vacationers. Conveniences like a firepit and a patio will help make your stay more 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 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.

Recent reviews of Winchester hotels
Expedia verified reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

5/5 Excellent
"Enjoyed our stay!"
A verified traveler from PAOLI stayed at Natural Bridge State Resort Park
Posted 1 day ago
Natural Bridge State Resort Park