Search the Best Cabins in Winchester

Find vacation rentals that suit your style

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Our top choices for Winchester cabin rentals

1. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,141 reviews)
"Love staying here, such easy access to the Gorge and Natural Bridge. Always convenient and easy to deal with. Always a place I keep in mind when I’m staying in the area."
United States
Logan
$70 nightly
The price is $77
Dec 6 - Dec 7
Total with taxes and fees
Natural Bridge State Resort Park

2. 1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (86 reviews)
"This house has a lot of character. It's quiet and peaceful while also being close to Lexington and historic sites."
United States
Barbara H.
$209 nightly
The price is $243
Nov 16 - Nov 17
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate

3. Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (114 reviews)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveler
$155 nightly
The price is $180
Nov 17 - Nov 18
Total with taxes and fees
Unique Stay in a 1907 Log Cabin on The Kentucky River

4. Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (134 reviews)
"It was a great cozy place for a weekend for me and my sister. It had everything we needed and we especially loved having the window bed! Would definitely consider staying here again."
United States
Anonymous traveler
$184 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

5. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (82 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
$428 nightly
The price is $465
Nov 16 - Nov 17
Total with taxes and fees
Cabin in Kentucky Horse Country

6. Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge

Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge
Stanton
10.0 out of 10, Exceptional, (141 reviews)
"This was an absolutely cool little private spot. Exactly what my lady and I were looking for."
United States
john m.
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees
Romantic RRG Cabin • Private Hot Tub • Amazing Views • Near Natural Bridge

7. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.4 out of 10, Very good, (9 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
$179 nightly
The price is $196
Nov 17 - Nov 18
Total with taxes and fees
New, Cozy, Secluded Cabin

8. Dappled Grey Cabin with hot tub at Red River Gorge

Dappled Grey Cabin with hot tub at Red River Gorge
Stanton
10.0 out of 10, Exceptional, (8 reviews)
"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"
United States
Jessica
$162 nightly
The price is $166
Nov 17 - Nov 18
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge

9. Social Distance/127 Private Acres -Hot Tub -Wi-Fi

Social Distance/127 Private Acres -Hot Tub -Wi-Fi
Irvine
9.6 out of 10, Exceptional, (4 reviews)
"This place is the definition of seclusion. It is so peaceful here. Very nice cabin with plenty of room for a family or a few friends. Only 30 minutes from the gorge and it was a pleasant drive to get there with many options to eat and shop. I highly recommend Toads BarN grill and definitely Miguel’s pizza. The hot tub was a fantastic treat to come back to after long days of hiking. It was very clean and heated up waiting for us. Very secluded and you hear nothing but the sounds of nature. Beds...
United States
Tyler N.
$315 nightly
The price is $326
Nov 30 - Dec 1
Total with taxes and fees
Social Distance/127 Private Acres -Hot Tub -Wi-Fi

10. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (100 reviews)
"Great little place , clean and comfortable quiet nice place to just relax for a few days and take in the fresh air"
United States
Jason B.
$149 nightly
The price is $164
Nov 16 - Nov 17
Total with taxes and fees
Mountain Memories Cabin

11. Trailer Parking/Hot Tub/King Size Beds/Mt Views

Trailer Parking/Hot Tub/King Size Beds/Mt Views
Stanton
10.0 out of 10, Exceptional, (1 review)
"Here’s a polished version of your review:We had a wonderful stay at this cabin with another couple. The accommodations were excellent — comfortable, clean, and very well stocked with everything we needed. It truly felt like a hidden gem, especially with the ample parking space for our trailers, which can be hard to find. We loved relaxing around the fire pit in the evenings after a long day. We thoroughly enjoyed our stay and will definitely be coming back soon!"
United States
Sarah G.
$262 nightly
The price is $288
Nov 17 - Nov 18
Total with taxes and fees
Trailer Parking/Hot Tub/King Size Beds/Mt Views

12. Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods

Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods
Stanton
10.0 out of 10, Exceptional, (345 reviews)
"great secluded property with everything we needed for a great weekend. Hot Tub was nice after a day of hiking."
United States
Kenneth
$257 nightly
The price is $283
Nov 19 - Nov 20
Total with taxes and fees
Private RRG Cabin • Hot Tub • 2BR • Secluded in the Woods

13. Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape

Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape
Stanton
10.0 out of 10, Exceptional, (51 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees
Romantic Red River Gorge Cabin • Private Hot Tub • Secluded Escape

14. Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape

Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape
Stanton
10.0 out of 10, Exceptional, (183 reviews)
"Loved the secluded atmosphere"
United States
Andrea
$235 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees
Romantic Red River Gorge Cabin • Hot Tub • Quiet Escape

15. 3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.8 out of 10, Exceptional, (10 reviews)
"This house was amazing for our little friend group! Very clean, and has a rope swing outside along with the ping pong table. My friends and I loved staying in this house!"
United States
Dakota S.
$218 nightly
The price is $240
Nov 16 - Nov 17
Total with taxes and fees
3 Miles Hollerwood/ATV Parking/Mountain Views

16. Private | Hot Tub | Stargazing | Mountain View

Private | Hot Tub | Stargazing | Mountain View
Stanton
9.8 out of 10, Exceptional, (8 reviews)
"Great for a nice weekend getaway! House was very clean and close to all the gift shops & activities!"
United States
Kiersten R.
$307 nightly
The price is $330
Dec 16 - Dec 17
Total with taxes and fees
Private | Hot Tub | Stargazing | Mountain View

17. Sandstone-Cozy Cliffside Cabin, Hot Tub + Fire Pit

Sandstone-Cozy Cliffside Cabin, Hot Tub + Fire Pit
Stanton
$280 nightly
The price is $309
Nov 24 - Nov 25
Total with taxes and fees
Sandstone-Cozy Cliffside Cabin, Hot Tub + Fire Pit

18. Cozy RRG Cabin • King Beds • Hot Tub • Views

Cozy RRG Cabin • King Beds • Hot Tub • Views
Stanton
10.0 out of 10, Exceptional, (392 reviews)
"The whole stay was awesome.. will definitely be back...😍😍😍"
United States
Edith
$265 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees
Cozy RRG Cabin • King Beds • Hot Tub • Views

19. Plum Crazy: Hot Tub Cabin in Frenchburg

Plum Crazy: Hot Tub Cabin in Frenchburg
Frenchburg
9.6 out of 10, Exceptional, (17 reviews)
"This is the perfect little cabin for a getaway! It was clean, had all the amenities we needed, and the hot tub was a huge plus."
United States
Robert
$265 nightly
The price is $292
Nov 16 - Nov 17
Total with taxes and fees
Plum Crazy: Hot Tub Cabin in Frenchburg

20. Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.4 out of 10, Very good, (47 reviews)
"This was a great place for a weekend stay."
United States
Schuyler W.
$190 nightly
The price is $209
Nov 17 - Nov 18
Total with taxes and fees
Quaint, heavily forested cabin, mountain valley view.
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.

Learn more about Winchester

Stroll through charming downtown streets lined with local shops and eateries. Tee off at Cassell Creek or Southwind Golf Course, then explore local history at the Bluegrass Heritage Museum.

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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 $77 and $464 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 $77 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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