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.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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 traveller
The price is €168
includes taxes & fees
9 Aug - 10 Aug
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)
"Excellent stopover. "
United States
Robert W.
The price is €215
includes taxes & fees
25 Aug - 26 Aug
1800’s Historical Log Cabin near I-75 Interstate
Exterior

3. Hike on Inn!

Hike on Inn!
Clay City
The price is €259
includes taxes & fees
31 Aug - 1 Sept
Hike on Inn!
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, (121 reviews)
"great place!"
United States
Ava G.
The price is €169
includes taxes & fees
9 Aug - 10 Aug
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, (1,985 reviews)
"Clean room and good continental breakfast."
United States
Jeff
The price is €87
includes taxes & fees
20 Aug - 21 Aug
Natural Bridge State Resort Park
Exterior

6. 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.
The price is €172
includes taxes & fees
13 Aug - 14 Aug
New, Cozy, Secluded Cabin
Exterior

7. 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
The price is €221
includes taxes & fees
3 Sept - 4 Sept
Dappled Grey Cabin with hot tub at Red River Gorge
Exterior

8. Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (86 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.
The price is €158
includes taxes & fees
16 Aug - 17 Aug
Mountain Memories Cabin
Exterior

9. 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.
The price is €429
includes taxes & fees
13 Aug - 14 Aug
Cabin in Kentucky Horse Country
Exterior

10. "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, (19 reviews)
"Cabin was beautiful no complaints "
United States
Dana S.
The price is €205
includes taxes & fees
10 Aug - 11 Aug
"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Exterior

11. 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, (326 reviews)
"The hot tub was very nice and a very private "
United States
Donnie W.
The price is €251
includes taxes & fees
9 Aug - 10 Aug
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Exterior

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

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (55 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is €185
includes taxes & fees
13 Aug - 14 Aug
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Exterior

13. Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge

Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Stanton
9.8 out of 10, Exceptional, (14 reviews)
"The cabin was nice and clean. Really liked the covered porch and deck area. Hot tub was clean and the temperature was perfect! I would stay there again"
United States
John P.
The price is €217
includes taxes & fees
17 Aug - 18 Aug
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Exterior

14. Tiny Cabin At The Pond

Tiny Cabin At The Pond
Stanton
9.4 out of 10, Exceptional, (23 reviews)
"Loved the friendly Donkeys! Very relaxing location."
United States
Sharon C.
The price is €173
includes taxes & fees
9 Aug - 10 Aug
Tiny Cabin At The Pond
Exterior

15. Hot Tub Dome with Epic Ridge Views - Cardinal Crest

Hot Tub Dome with Epic Ridge Views - Cardinal Crest
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"This place was perfect for what I needed, a little space from the world and back to nature. Will be back. "
United States
Danny P.
The price is €264
includes taxes & fees
12 Aug - 13 Aug
Hot Tub Dome with Epic Ridge Views - Cardinal Crest
Exterior

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

Hot Tub Dome with Epic Ridge Views- Sunrise Summit
Stanton
9.6 out of 10, Exceptional, (5 reviews)
"Great views with a nicely decorated place to stay"
United States
Zack L.
Hot Tub Dome with Epic Ridge Views- Sunrise Summit
Exterior

17. 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, (134 reviews)
"Cute little spot to stay, the view and hot tub is incredible, both day & night. "
United States
Tawny Freber- S.
The price is €236
includes taxes & fees
9 Aug - 10 Aug
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
Exterior

18. PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB

PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Stanton
10.0 out of 10, Exceptional, (31 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is €236
includes taxes & fees
11 Aug - 12 Aug
PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Exterior

19. 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, (375 reviews)
"Great location, not too far of a drive to many trails. Great place to spend our 25th anniversary!"
United States
Laura H.
The price is €260
includes taxes & fees
9 Aug - 10 Aug
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
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.
The price is €258
includes taxes & fees
7 Aug - 8 Aug
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.
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Top Winchester Hotel Reviews

Hyatt Place Lexington

Hyatt Place Lexington

10/10 Excellent
"Large room for our toddler to run around but sadly the carpet turned her feet/socks black. The shower head was also nearly impossible to fully turn off which explains the rust on the drain."
Daniel 1-night trip
Posted 4 hours ago
Hyatt Place Lexington

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
1,484
Accommodation
234 Cabin Rentals
Lowest Price
€87
Highest Price
€429

Frequently asked questions

What are the best cabins near Winchester?
Ranging from rustic and small to large and luxurious, you have 607 cabins on offer in and around Winchester. Some popular options include 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 €87 and €429 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?
Get set to treat yourself to a stay to remember at one of our Winchester luxury cabins. Cabin - Hot Tub, Wifi, No Pet Fee - Beary Cosy is one place where you can spend a few days or more living the high life. It features a deck and a spa tub. Or, use 2 Bed Cabin Hot Tub - Fire Pit as a base to explore the impressive natural areas around you. Quality touches here include a deck and a spa tub.
What are the best river cabins near Winchester?
If you're seeking a comfy hideaway by the water, a Winchester river cabin will be just the thing. Put your feet up at Hot Tub, Wifi, Adventure - New Family Cabin and let any worries on your mind disappear downstream. Handy amenities here include nearby ecotour services and a queen bed. Another top riverside property is Cabin - Pet - Friendly And Great Location. Guests have use of pet-friendly facilities, a deck and more.
What are the best cabins with pools near Winchester?
Slip on your swimsuit and go for a dip whenever you want when you stay at one of our cabin rentals with a pool near Winchester. Cosy East Bernstadt Cabin With Porch + Fishing Lake is a favourite among travellers. A porch and a patio are some other amenities you'll find here. Or you can enjoy a break from the hustle and bustle 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 some time out in nature but aren't into roughing it, a cabin is a perfect solution. Book a few nights or longer at Cabin - Sits On 8 Private Acres, Hiking Trails At This Secluded Chalet Wi. This property comes with an oven, a stovetop and more. You can also experience comfort and outdoor fun rolled into one at Cave Run Red River Gorge Cabin. A firepit and a garden are among its 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. Swap your cramped office for a few days in the great outdoors at Hot Tub, Wifi, Adventure - New Family Cabin. A porch and a patio are some of the amenities it comes with. Alternatively, forget all about work at Secluded Cabin On 70 Acres Private Land. Put your bags down here and enjoy access to 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 €87 per night.
Can I find log cabins in Winchester?
For lots of nature lovers, the ideal outdoor holiday isn't complete without bunking down in a cosy log cabin. Get exploring or simply slow down and relax at Big Rock Log Cabin, Beside Natural Bridge. Recreational activities such as picnicking and hiking are within easy reach here. Another attractive log cabin getaway is Hot Tub, Wifi, Adventure - Family Log Cabin. Canoeing and quad biking will keep you active when you're not happily hibernating in your rustic hideaway.
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 cabin travellers. Some amenities here include a patio and a firepit. Cosy Secluded Cabin With Wi - Fi is another fantastic choice. Conveniences such as a porch and a patio will help make your stay happy and 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 further 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 holiday that's big on charm, value for money and home comforts, a cabin is the best choice. Leave your city blues behind and wander through the greenery of nature. From days spent hiking to peaceful nights cuddled up by the fire, cabins offer both excitement and relaxation. Check out all the great Winchester options right here on Expedia.
What are the top nature cabins in Winchester?
Escape to Hot Tub, Wifi, Adventure - New Family Cabin and let all your worries drift downstream. Activities such as nearby rock climbing and cycling help make this river cabin in Winchester a hit with travellers. Cabin - Pet - Friendly And Great Location is another getaway where you can hang out in nature. If you're in the mood for adventure, try nearby mountain biking and nearby fishing.
What are some of the best cabins near Bluegrass Heritage Museum in Winchester?
Leave the noisy city behind and venture into nature from a Bluegrass Heritage Museum cabin. Get up close to wildlife, take in the fresh air and then settle back at Secluded Getaway In Beautiful New Cabin Near Red River Gorge. Popular activities such as paddle boating and nearby fishing are mere moments away here. Another place where you'll feel right at home is Hot Tub, Wifi, Pet - Friendly - Cosy Tiny Cabin. Nearby fishing and hiking are a few things to keep you busy during your stay.

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