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 Cabin Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winchester cabin rentals

Terrace/patio

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,939 reviews)
"Great area Nice place to stay"
United States
Julie
The price is HK$995
HK$1,097 total
includes taxes & fees
12 Jul - 13 Jul
Natural Bridge State Resort Park
Living area

3 Miles Hollerwood/ATV Parking/Mountain Views

3 Miles Hollerwood/ATV Parking/Mountain Views
Zoe
9.4 out of 10, Exceptional, (3 reviews)
"Remote and nice location with plenty of room. "
United States
Keith P.
The price is HK$572
HK$2,005 total
includes taxes & fees
29 Jun - 30 Jun
3 Miles Hollerwood/ATV Parking/Mountain Views
Exterior

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Stanton
9.8 out of 10, Exceptional, (24 reviews)
"Wonderful location and cabin is very spacious "
United States
Anonymous traveller
The price is HK$1,888
HK$4,036 total
includes taxes & fees
28 Jun - 29 Jun
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
Exterior

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (78 reviews)
"Would stay again. Responsive host, property was very clean and host had left nice touches / decorations for valentines day weekend visit."
United States
Robert C.
The price is HK$1,058
HK$1,521 total
includes taxes & fees
5 Jul - 6 Jul
Mountain Memories Cabin
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, (367 reviews)
"Great spot for weekend getaway. "
United States
Liz A.
The price is HK$1,408
HK$2,469 total
includes taxes & fees
28 Jun - 29 Jun
YOU WILL LOVE THIS ONE!-SUPER CLEAN-KING BEDS-HOT TUB-VIEW-HI SPEED WIFI-BOOK IT
Exterior

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, (112 reviews)
"great place!"
United States
Ava G.
The price is HK$692
HK$1,515 total
includes taxes & fees
5 Jul - 6 Jul
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge
Exterior

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (48 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is HK$1,334
HK$1,669 total
includes taxes & fees
5 Jul - 6 Jul
Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Exterior

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Frenchburg
9.6 out of 10, Exceptional, (13 reviews)
"Fun place to stay for 2!"
United States
Bob R.
The price is HK$949
HK$2,470 total
includes taxes & fees
28 Jun - 29 Jun
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
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
The price is HK$857
HK$1,473 total
includes taxes & fees
2 Jul - 3 Jul
Larkspur Cabin with Hot Tub near Red River Gorge
Exterior

Love Shack

Love Shack
Stanton
The price is HK$610
HK$1,537 total
includes taxes & fees
28 Jun - 29 Jun
Love Shack
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, (131 reviews)
"Cute little spot to stay, the view and hot tub is incredible, both day & night. "
United States
Tawny Freber- S.
The price is HK$1,259
HK$2,235 total
includes taxes & fees
28 Jun - 29 Jun
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL
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)
"Cabin was beautiful no complaints "
United States
Dana S.
The price is HK$787
HK$1,862 total
includes taxes & fees
28 Jun - 29 Jun
"Alpine Hills" Cozy Hideaway RRG Cabin w/ Hot Tub
Exterior

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
9.6 out of 10, Exceptional, (9 reviews)
"Very responsive host. Cabin has lots of charm. Location is fairly remote- follow directions given by host and not those from google maps….latter can lead you to the wrong spot/a turn-off that’s not actually a road. "
United States
Matthew P.
The price is HK$896
HK$2,008 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Oak Hideaway | 3BR Cabin Retreat w/Hot Tub Near Red River Gorge
Exterior

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, (28 reviews)
"Love the area and the stay was great! Thanks for the communication we had a great time. "
United States
Holly,
The price is HK$1,325
HK$2,316 total
includes taxes & fees
14 Jul - 15 Jul
PRIVATE SHIPPING CONTAINER CABIN IN THE WOODS-RED RIVER GORGE-VERY CLEAN-HOT TUB
Exterior

New, Cozy, Secluded Cabin

New, Cozy, Secluded Cabin
Jeffersonville
8.0 out of 10, Very good, (6 reviews)
"Great host, beautiful property, exactly as listed, steep driveway entrance but awesome overall!"
United States
Edgar O.
The price is HK$831
HK$1,487 total
includes taxes & fees
2 Jul - 3 Jul
New, Cozy, Secluded Cabin
Exterior

"Cloud Chaser" - Overlook Dome 005 in RRG

"Cloud Chaser" - Overlook Dome 005 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Amazing place to stay"
United States
Isaiah F.
The price is HK$1,082
HK$2,126 total
includes taxes & fees
28 Jun - 29 Jun
"Cloud Chaser" - Overlook Dome 005 in RRG
Exterior

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$1,082
HK$2,127 total
includes taxes & fees
28 Jun - 29 Jun
"Cardinal Crest" - Overlook Dome 002 in RRG
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, (326 reviews)
"Wonderful place to stay. We loved it!"
United States
Jamie B.
The price is HK$1,482
HK$2,558 total
includes taxes & fees
12 Jul - 13 Jul
BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK
Exterior

Mountaintop Cabin - Hot Tub - Natural Bridge 3mile

Mountaintop Cabin - Hot Tub - Natural Bridge 3mile
Stanton
9.6 out of 10, Exceptional, (4 reviews)
"We planned a quick weekend to RRG and this cabin was perfect! It was close to everything we wanted to explore and all the recommended restaurants were just a few miles away. Beds were comfy and the hot tub is always a plus. Thank you!"
United States
Jessica M.
The price is HK$603
HK$1,945 total
includes taxes & fees
30 Jun - 1 Jul
Mountaintop Cabin - Hot Tub - Natural Bridge 3mile
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, (165 reviews)
"The place was great!! Hot tub was a nice addition. The property was clean, quiet and relaxing! I would stay again if in the area!!"
United States
Denise M.
The price is HK$1,259
HK$2,235 total
includes taxes & fees
30 Jun - 1 Jul
STOP SCROLLING!-HOT TUB-HIGH SPEED WIFI-SUPER CLEAN-NATURAL BRIDGE-NADA TUNNEL
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

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent
"Clean room and plenty parking"
Keisha 2-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Find out more about Winchester

Winchester Cabin Rentals information

Number of reviews
1,129
Accommodation
235 Cabin Rentals
Lowest Price
HK$1,096
Highest Price
HK$4,036

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 HK$1,096 and HK$4,036 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 HK$1,096 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.

Explore a world of travel with Expedia