Search the Best Cabins in Winchester

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winchester cabin rentals

Hiking

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,887 reviews)
"Beautiful area, surrounded by woods and hiking trials. Food and staff was exceptional! Highly recommend."
United States
Terrance
$121 nightly
The price is $133
Jun 14 - Jun 15
Total with taxes and fees
Natural Bridge State Resort Park
Exterior detail

"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (14 reviews)
"Great location "
United States
Zach M.
$197 nightly
The price is $217
May 18 - May 19
Total with taxes and fees
"Rocky Top" - Cozy RRG Cabin
Exterior

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (73 reviews)
"We loved our stay. If you want a quiet out of the way get-a-way, this it it! The cabin was very clean and had what we needed. We had the pleasure of meeting the host in person when he brought us fire wood and he was very nice. We enjoyed feeding the donkeys and meeting the neighboring dogs who were super friendly. We would definitely stay here again."
United States
Lisa
$177 nightly
The price is $195
May 18 - May 19
Total with taxes and fees
Mountain Memories Cabin
Exterior

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Stanton
10.0 out of 10, Exceptional, (321 reviews)
"Great stay! Loved the private driveway. "
United States
Emily N.
$263 nightly
The price is $289
May 18 - May 19
Total with taxes and fees
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Exterior

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (128 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
$257 nightly
The price is $283
May 18 - May 19
Total with taxes and fees
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
1 bedroom, iron/ironing board, travel crib, WiFi

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (5 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
$221 nightly
The price is $243
May 18 - May 19
Total with taxes and fees
"Cardinal Crest" - Overlook Dome 002 in RRG
Exterior

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT

YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Stanton
10.0 out of 10, Exceptional, (361 reviews)
"Great place and location, would stay again!"
United States
Larry D.
$286 nightly
The price is $315
May 24 - May 25
Total with taxes and fees
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Exterior

"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub

"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Stanton
9.4 out of 10, Exceptional, (18 reviews)
"Greet stay, loved the hot tub next to the creek. Quiet and felt secluded / peaceful "
United States
Dan B.
$215 nightly
The price is $236
May 19 - May 20
Total with taxes and fees
"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Exterior

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion

Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
Irvine
9.8 out of 10, Exceptional, (15 reviews)
"Perfect little get away for our anniversary! We had a great time exploring Red River Gorge and it was nice having a place like this to come back to. We cooked breakfast every morning on the griddle and the tutorial video for the pellet stove was much appreciated!"
United States
Jacob S.
$194 nightly
The price is $214
May 18 - May 19
Total with taxes and fees
Tin Cantina - Cozy Tiny Cabin Near Red River Gorge - Stargazing & Seclusion
Exterior

Larkspur Cabin with Hot Tub near Red River Gorge

Larkspur Cabin with Hot Tub near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (11 reviews)
"Cabin was immaculate, instructions were clear, host was communicative, easy to reach and friendly. We were driving across the country and was a very much needed peaceful stay. Lovely place to stay. "
United States
ElyCilia
$164 nightly
The price is $169
May 20 - May 21
Total with taxes and fees
Larkspur Cabin with Hot Tub near Red River Gorge
Exterior detail

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL

STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Stanton
10.0 out of 10, Exceptional, (163 reviews)
"Everything was so clean and organized, easy check in-check out directions, secluded but close enough to restaurants and hikes! Would highly recommend! "
United States
Matt C.
$246 nightly
The price is $271
May 18 - May 19
Total with taxes and fees
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
Exterior

Just 1 mile from Natural Bridge State Park!

Just 1 mile from Natural Bridge State Park!
Slade
8.8 out of 10, Excellent, (29 reviews)
"The house was very welcoming and the cabin was beautiful"
United States
Sherry Z.
$219 nightly
The price is $241
May 20 - May 21
Total with taxes and fees
Just 1 mile from Natural Bridge State Park!
Outdoor dining

Tiny Cabin At The Pond

Tiny Cabin At The Pond
Stanton
9.8 out of 10, Exceptional, (20 reviews)
"Stayed one night and enjoyed the peaceful area. The placed had everything we needed. We enjoyed the fire pit and pond. "
United States
Marvin D.
$179 nightly
The price is $198
May 18 - May 19
Total with taxes and fees
Tiny Cabin At The Pond
Exterior

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (45 reviews)
"The cabin was very clean and absolutely beautiful! Check in was a breeze and host was very kind."
United States
Stacy B.
$192 nightly
The price is $212
May 21 - May 22
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Exterior

Cabin for two with an awesome view

Cabin for two with an awesome view
Stanton
9.2 out of 10, Wonderful, (40 reviews)
"What a lovely cabin! We had a blast. You can tell that someone put a lot of thought into the decor and amenities. Perfect for outdoor folks! The driveway is TRICKY for a light vehicle but that's hardly a detractor. "
United States
Kyle K.
Cabin for two with an awesome view
Exterior

Chalet style cabin with loft bedroom, hot tub and internet

Chalet style cabin with loft bedroom, hot tub and internet
Stanton
9.2 out of 10, Wonderful, (41 reviews)
"Our experience was great, cabin was beautiful and had an awesome time!"
United States
Tiffany G.
$343 nightly
The price is $360
May 25 - May 26
Total with taxes and fees
Chalet style cabin with loft bedroom, hot tub and internet
WiFi, bed sheets

Love Shack

Love Shack
Stanton
$178 nightly
The price is $196
May 18 - May 19
Total with taxes and fees
Love Shack
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, (22 reviews)
"Communication was great. Sweet little secluded place with awesome land for exploring. We hiked back to a beautiful waterfall."
United States
Kaela N.
$272 nightly
The price is $298
May 18 - May 19
Total with taxes and fees
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
Exterior

Hot Tub! Tiny House Retreat in the Woods

Hot Tub! Tiny House Retreat in the Woods
Stanton
8.0 out of 10, Very Good, (11 reviews)
"Amazing little place in the heart of RRG"
United States
Madelyn B.
$165 nightly
The price is $182
May 21 - May 22
Total with taxes and fees
Hot Tub! Tiny House Retreat in the Woods
Exterior

"Cloud Chaser" - Overlook Dome 005 in RRG

"Cloud Chaser" - Overlook Dome 005 in RRG
Stanton
10.0 out of 10, Exceptional, (4 reviews)
"Amazing place to stay"
United States
Isaiah F.
$227 nightly
The price is $250
May 20 - May 21
Total with taxes and fees
"Cloud Chaser" - Overlook Dome 005 in RRG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Quality Inn Lexington -Horse Park

Quality Inn Lexington -Horse Park

10/10 Excellent
"Clean room. Traveling alone & I felt safe there. Check in was smooth & it was quiet. Breakfast was sufficient, but nothing extraordinary. Easy to get to from LEX airport."
Amy 1-night trip
Posted 3 hours ago
Quality Inn Lexington -Horse Park

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
3,083
Accommodation
231 Cabin Rentals
Lowest Price
$133
Highest Price
$360

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 $133 and $360 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 $133 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.

Explore a world of travel with Expedia