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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Outdoor pool
Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1310)
"Very good with good service and information at the desk. Great hike to the bridge!"
The price is ￥19,775
￥21,800 total
includes taxes & fees
Jun 6 - Jun 7
Natural Bridge State Resort Park
Fridge, oven, stovetop, coffee/tea maker
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (242)
"The cabin was amazing. Nice and peaceful location. The cabin had everything that we needed. The jacuzzi was nice and relaxing, My wife enjoyed it very much! We are planning to get one at home shortly. The location of the property was a little puzzling at first. When we started to venture of and visit locations. The placement of the property made perfect sense! You’re literally right in the middle of everything that you will want to see! Everything interesting is just a few miles away! My wife...
The price is ￥20,411
￥38,148 total
includes taxes & fees
Jun 12 - Jun 13
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Pool
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (96)
"We loved how secluded it was, but close to the park and restaurants. The hot tub and fire pit were a nice addition. It was well decorated and felt upscale. I liked that it had k-cups. Love the travel pics on the wall. We had a great time and enjoyed the accommodations. Overall a wonderful get away. We will definitely be back!"
The price is ￥21,824
￥36,867 total
includes taxes & fees
Jun 9 - Jun 10
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
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Outdoor spa tub
Shipping Container Den-Hot Tub!-View! FREE FIREWOOD for May and June weeknights!
10.0 out of 10, Exceptional, (52)
"Had a kid free weekend with the wife. Great location, very clean, and everything we needed. Would def stay again"
The price is ￥18,684
￥33,060 total
includes taxes & fees
May 27 - May 28
Shipping Container Den-Hot Tub!-View! FREE FIREWOOD for May and June weeknights!
Fridge, microwave, oven, stovetop
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
10.0 out of 10, Exceptional, (250)
"The property was lovely and very close to many hiking spots! It was spacious and the accommodations were lovely!"
The price is ￥20,254
￥37,732 total
includes taxes & fees
May 27 - May 28
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
Exterior
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
10.0 out of 10, Exceptional, (235)
"Canisters is a really neat ideas"
The price is ￥22,729
￥40,954 total
includes taxes & fees
Jun 10 - Jun 11
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
Property grounds
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
9.2 out of 10, Wonderful, (130)
"Fun relaxing cabin in the woods"
The price is ￥22,986
￥44,023 total
includes taxes & fees
May 30 - May 31
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
Exterior
Nestled in the beautiful mountains of the Red River Gorge Area
8.0 out of 10, Very Good, (1)
"The cabin was clean enough except for the linens that smelled of cigarette smoke. We had a problem with check-in due to not receiving an entry code from VRBO. With no cell service, we had to drive to find reception to call the Scenic Cabin rentals for our code. Fortunately, we arrived during daylight hours."
Nestled in the beautiful mountains of the Red River Gorge Area
Outdoor dining
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
10.0 out of 10, Exceptional, (233)
"Fantastic property. Owner is responsive and friendly without being too much. Top notch. Will stay again!"
The price is ￥22,729
￥39,664 total
includes taxes & fees
Jun 5 - Jun 6
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Property grounds
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (117)
"The cabin was what we were looking for, quite secluded and wooded with a hot tub. It was nice and clean and we enjoyed soaking in the tub to the pouring rain on the tin roof. The cabin cat outside was cute. The drawback is to make sure to check your dates! At booking. It defaulted to different dates than we wanted. Then continued to show other options for other cabins on the dates we wanted. Double check before you pay. The positive was that the staff were great communicators and patient when...
The price is ￥18,421
￥37,344 total
includes taxes & fees
Jun 10 - Jun 11
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Exterior
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (38)
"After both of us working super hard in 2024 non stop, we needed a quiet little getaway from society. This was perfect! We put our phones away for a few days and just spent quality time together! I highly recommend this cabin for anyone looking to take a break from the real world! Lol"
The price is ￥16,139
￥32,629 total
includes taxes & fees
May 30 - May 31
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Property grounds
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (105)
"We had a wonderful time. The cabin was clean and comfortable. It is close to a lot of great hiking trails. There’s a grocery store, several restaurants, and gas stations all close by. Would definitely stay here again!"
The price is ￥24,330
￥44,828 total
includes taxes & fees
May 30 - May 31
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
Property grounds
Treetops on Garden
10.0 out of 10, Exceptional, (58)
"Perfect for is for UK graduation weekend. We like to stay close to where our daughter lives. We rented upstairs and downstairs too. Great neighborhood!"
Treetops on Garden
Interior
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
8.2 out of 10, Very Good, (90)
"Loved the secluded area and the cabin was lovely"
The price is ￥23,149
￥41,456 total
includes taxes & fees
Jun 10 - Jun 11
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!
Interior
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
8.8 out of 10, Excellent, (32)
"Could use some updating and tlc. Wasnt a issue but there was only enough seat place for 3 people to watch tv. All in all it was fine and we enjoyed our stay."
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Exterior
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
9.4 out of 10, Exceptional, (51)
"My boyfriend and I stayed there for three night's and 4 days. The place was perfectly located by both the parks and close to everything we needed. However, getting up to the cabin was an adventure of itself as it's located up pretty high with steep hills and sharp turns, so being a confident/comfortable driver is a must. The cabin was very neat and clean and included everything we needed for our stay, even a coffee and popcorn maker. My only complaint was that the stairs matched the steep hill...
The price is ￥24,127
￥41,824 total
includes taxes & fees
May 28 - May 29
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Property grounds
Furnished Teepee/Glamping/Kayak Ramp Access on the Red River
9.8 out of 10, Exceptional, (8)
"Best experience ever"
The price is ￥11,004
￥22,500 total
includes taxes & fees
May 27 - May 28
Furnished Teepee/Glamping/Kayak Ramp Access on the Red River
Fridge, microwave, oven, stovetop
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
9.2 out of 10, Wonderful, (18)
"I stayed in Lexington for a week for my son’s surgery. This house had everything I needed. A nice back yard for my dog to romp and play. Close proximity to food and medical center Will definitely be back"
The price is ￥15,701
￥31,873 total
includes taxes & fees
May 27 - May 28
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
Exterior
Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!
9.2 out of 10, Wonderful, (46)
"Nice, clean place. Comfortable and private. It was a little out of the way from Red River Gorge - about 25 minute drive. It was great for the three of us, not sure I’d want to try and add a 4th. The kids loved the pac man game!!"
The price is ￥14,509
￥27,928 total
includes taxes & fees
Jun 5 - Jun 6
Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!
Fridge, microwave, oven, stovetop
Studio Cabin near the Red River Gorge
8.8 out of 10, Excellent, (3)
"Perfect location to hit up the trails. Very clean, had all the amenities we needed. We’ll be back!"
Studio Cabin near the Red River Gorge
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Front of property
Quality Inn Lexington -Horse Park
2.5 star property
8.4 out of 10, Very Good, (971)
"Ease of check in. "
The price is ￥12,383
￥14,374 total
includes taxes & fees
May 28 - May 29
Quality Inn Lexington -Horse Park
Interior
Embassy Suites by Hilton Lexington Green
3.5 star property
9.2 out of 10, Wonderful, (1003)
"The free snacks were a great addition!"
The price is ￥21,887
￥25,404 total
includes taxes & fees
Jun 20 - Jun 21
Embassy Suites by Hilton Lexington Green
Lobby
GuestHouse Lexington
2.5 star property
8.2 out of 10, Very Good, (1001)
"Good place"
The price is ￥10,534
￥12,227 total
includes taxes & fees
Jun 9 - Jun 10
GuestHouse Lexington
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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Frequently asked questions

Are there vacation rentals in Winchester?

Yes, we offer vacation rentals close to top points of interest in Winchester, or you can choose a more secluded option if you want a relaxing place to stay. Our travelers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffeehouses and shopping during your trip.

What are some of the best vacation home rentals that Winchester has to offer?

Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital: You might want to consider this vacation home rental near Winchester, which is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winchester?

Expedia has 7 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Lykins Park and Community Park are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Southwind Golf Course and Cassell Creek Golf Course are other places to visit while you're in town.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winchester. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Recent reviews of Winchester properties
Expedia verified reviews

The Manchester

The Manchester

5/5 Excellent
"Great place"
A verified traveler stayed at The Manchester
Posted 1 day ago
The Manchester