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.

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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester cabin rentals

Exterior

1. 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, (112 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
$163 nightly
The price is $189
Aug 31 - Sep 1
Total with taxes and fees
Unique Stay in a 1907 Log Cabin on The Kentucky River
Exterior detail

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, (75 reviews)
"It was really great staying in a historical home. It was clean and very comfortable."
United States
Nancy L.
$209 nightly
The price is $243
Aug 31 - Sep 1
Total with taxes and fees
1800’s Historical Log Cabin near I-75 Interstate
Exterior

3. 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
$191 nightly
The price is $197
Sep 3 - Sep 4
Total with taxes and fees
Dappled Grey Cabin with hot tub at Red River Gorge
Exterior

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, (123 reviews)
"great place!"
United States
Ava G.
$175 nightly
The price is $193
Sep 1 - Sep 2
Total with taxes and fees
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Terrace/patio

5. Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (2,019 reviews)
"Great place to stay."
United States
Monty
$106 nightly
The price is $117
Sep 13 - Sep 14
Total with taxes and fees
Natural Bridge State Resort Park
Exterior

6. The Lakeview Cabin and Highland Retreat

The Lakeview Cabin and Highland Retreat
Clay City
10.0 out of 10, Exceptional, (1 review)
The Lakeview Cabin and Highland Retreat
Exterior

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

Social Distance/127 Private Acres -Hot Tub -Wi-Fi
Irvine
10.0 out of 10, Exceptional, (1 review)
"Beautiful cabin with in the woods. The hot tub was amazing with powerful jets. All the amenities on site for a fire, grilling and full kitchen. Was extremely quiet at nighttime with fireflies everywhere. Wanted to ride the side by side that is on premise. We should have asked if that was an option. Christie was very proactive with directions and communication as well. We are looking to come back in October. The Woodman's."
United States
Justin W.
$357 nightly
The price is $370
Aug 30 - Aug 31
Total with taxes and fees
Social Distance/127 Private Acres -Hot Tub -Wi-Fi
Exterior

8. Hike on Inn!

Hike on Inn!
Clay City
$287 nightly
The price is $316
Sep 8 - Sep 9
Total with taxes and fees
Hike on Inn!
Exterior

9. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (88 reviews)
"Our second visit here. Host very responsive, location great and very clean. Would recommend to anyone looking to visit the area."
United States
Robert C.
$174 nightly
The price is $192
Sep 1 - Sep 2
Total with taxes and fees
Mountain Memories Cabin
Exterior

10. New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.4 out of 10, Very Good, (7 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
$178 nightly
The price is $195
Aug 30 - Aug 31
Total with taxes and fees
New, Cozy, Secluded Cabin
Exterior

11. Cabin in Kentucky Horse Country

Cabin in Kentucky Horse Country
Bourbon County
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful cabin with wonderful views in a peaceful setting"
United Kingdom
Siobann S.
$450 nightly
The price is $489
Aug 30 - Aug 31
Total with taxes and fees
Cabin in Kentucky Horse Country
Exterior

12. Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (57 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
$195 nightly
The price is $215
Aug 30 - Aug 31
Total with taxes and fees
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Exterior

13. Hot Tub Dome with Epic Ridge Views- Sunrise Summit

Hot Tub Dome with Epic Ridge Views- Sunrise Summit
Stanton
9.8 out of 10, Exceptional, (7 reviews)
"Great views with a nicely decorated place to stay"
United States
Zack L.
$240 nightly
The price is $265
Sep 2 - Sep 3
Total with taxes and fees
Hot Tub Dome with Epic Ridge Views- Sunrise Summit
Exterior

14. Hot Tub Dome with Epic Ridge Views- Pineview Peak

Hot Tub Dome with Epic Ridge Views- Pineview Peak
Stanton
9.6 out of 10, Exceptional, (7 reviews)
"We loved staying here."
United States
Kelsey M.
$240 nightly
The price is $265
Aug 31 - Sep 1
Total with taxes and fees
Hot Tub Dome with Epic Ridge Views- Pineview Peak
Exterior detail

15. "Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.4 out of 10, Exceptional, (16 reviews)
"Great location "
United States
Zach M.
$191 nightly
The price is $211
Aug 30 - Aug 31
Total with taxes and fees
"Rocky Top" - Cozy RRG Cabin
Exterior

16. 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)
"My wife and I had a very relaxing get away. Lovely place for a couple."
United States
Anonymous traveler
$136 nightly
The price is $140
Aug 30 - Aug 31
Total with taxes and fees
Larkspur Cabin with Hot Tub near Red River Gorge
Exterior

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

"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Stanton
9.0 out of 10, Wonderful, (22 reviews)
"Cabin was beautiful no complaints "
United States
Dana S.
$203 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Living area

18. 3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.8 out of 10, Exceptional, (9 reviews)
"Remote and nice location with plenty of room. "
United States
Keith P.
$227 nightly
The price is $250
Aug 30 - Aug 31
Total with taxes and fees
3 Miles Hollerwood/ATV Parking/Mountain Views
Exterior

19. Spacious Secluded Cabin on 100 Acres Near Red River Gorge

Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Irvine
10.0 out of 10, Exceptional, (91 reviews)
"Clean, great outdoor space"
United States
Jen M.
$238 nightly
The price is $262
Aug 30 - Aug 31
Total with taxes and fees
Spacious Secluded Cabin on 100 Acres Near Red River Gorge
Exterior

20. Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (14 reviews)
"Fun place to stay for 2!"
United States
Bob R.
$269 nightly
The price is $297
Aug 30 - Aug 31
Total with taxes and fees
Plum Crazy: Frenchburg Cabin on 1 Acre
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

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

8/10 Good
"Clean rooms and pleasant staff. Breakfast was not included in our pricing. This would have been nice to have a breakfast buffet. Would recommend for families. Great location for shopping!"
Claudine 1-night trip
Posted 7 hours ago
Holiday Inn Lexington - Hamburg by IHG

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
2,718
Accommodation
242 Cabin Rentals
Lowest Price
$117
Highest Price
$489

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 $117 and $489 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 $117 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