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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

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 €223
per night
6 Jun - 7 Jun
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Outdoor spa tub
Shipping Container Den-Hot Tub!-View! FREE FIREWOOD for May and June weeknights!
10.0 out of 10, Exceptional, (51)
"We had a blast at this property. It’s perfect for a two person stay."
The price is €223
per night
3 Jun - 4 Jun
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)
"Host was quick to respond to any questions we had. Very clean cabin, peaceful, relaxing property."
The price is €225
per night
27 May - 28 May
The Original Shipping Container Cabin in Red River Gorge-Hot Tub and a View!
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Exterior
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
10.0 out of 10, Exceptional, (235)
"We loved everything about our stay in the shipping container. It was super clean & had everything we needed. We enjoyed sitting on the porch watching a turkey watching us. We had a fire & made hot dogs & s’mores. Our hosts were great! It was perfect!!!"
The price is €214
per night
22 May - 23 May
Shipping Container Cabin in the Woods of Red River Gorge-HotTub-Secluded-Private
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 €238
per night
3 Jun - 4 Jun
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Property grounds
Treetops on Garden
10.0 out of 10, Exceptional, (57)
"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
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 €254
per night
6 Jun - 7 Jun
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
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 €221
per night
29 May - 30 May
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - 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 €136
per night
23 May - 24 May
Furnished Teepee/Glamping/Kayak Ramp Access on the Red River
Exterior
The Wellington: Fire-pit; Walk to EKU & Town by I-75
9.8 out of 10, Exceptional, (61)
"Great location! We went to horse races at Keeneland on Saturday (about 40 minute drive) and hiked East Pinnacle in Berea College Forest on Sunday (about 20 minute drive). Beautiful and so much fun! House was spotless and included all necessary amenities. Host was very responsive to all my questions; provided lots of tips on dining options in area. EKU is just a block away! Beautiful campus to take a walk."
The price is €250
per night
22 May - 23 May
The Wellington: Fire-pit; Walk to EKU & Town by I-75
Interior
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (47)
"Quaint peaceful cottage with a great fire pit and hot tub. It was very comfortable and had all the coveniences. MI finca in town for really good mexican food was a plus. We went to RRG underground Kayak and climbed the Natural Bridge in one afternoon so it was so nice to come back to seclusion and relax in the hot tub. We would highly recommend it!!"
The price is €193
per night
22 May - 23 May
Hot Tub, WiFi, Pet-Friendly - Cozy Tiny Cabin - The Ridge at 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 €196
per night
22 May - 23 May
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 €278
per night
10 Jun - 11 Jun
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!
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 €251
per night
28 May - 29 May
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!
Interior
Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!
9.4 out of 10, Exceptional, (32)
"We had an absolute amazing time. A beautiful cabin with a beautiful view. Management was amazing and got right back to me when we needed something. We will be staying again."
The price is €253
per night
22 May - 23 May
Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!
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 €204
per night
22 May - 23 May
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!
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 €192
per night
27 May - 28 May
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 €167
per night
3 Jun - 4 Jun
Tiny Cabin - A Frame of Mind - near Red River Gorge Kentucky!
Property grounds
Eagle View RRG -Hot Tub-spacious!
9.2 out of 10, Wonderful, (5)
"Overall our group had a great experience at this property. A few minor issues were encountered but nothing major. It would be nice to have internet service and better cell service, but this didn't raise any complaints from the group. We could make calls after walking a short distance down the driveway. We had a group of 13 and had plenty of room. This property was very secluded. The road became a private drive just past the driveway."
Eagle View RRG -Hot Tub-spacious!
Interior
Hot Tub & No Pet Fee - Beary Secluded - Small Family Cabin in Red River Gorge, Kentucky!
9.0 out of 10, Wonderful, (73)
"Overall great time. The location was perfect for our purposes. The inside was clean and neat. The furniture was a little worn and broken down. The bedroom lights didn’t have shades, so the bare bulbs were harsh. The finishes in the bathroom were poorly done."
The price is €239
per night
30 May - 31 May
Hot Tub & No Pet Fee - Beary Secluded - Small Family Cabin in Red River Gorge, Kentucky!
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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

Lobby
GLō Best Western Lexington
3.0 star property
9.4 out of 10, Exceptional, (2266)
"the food/breakfast was great. The noise from the the floor above was high. I would definitely stay at a GLO best best western again"
The price is €117
per night
29 May - 30 May
GLō Best Western Lexington
Interior
Embassy Suites by Hilton Lexington Green
3.5 star property
9.2 out of 10, Wonderful, (1006)
"The staff especially Andy were the best ever."
The price is €150
per night
27 May - 28 May
Embassy Suites by Hilton Lexington Green
Front of property
Quality Inn Lexington -Horse Park
2.5 star property
8.4 out of 10, Very good, (966)
"It’s a clean budget motel"
The price is €76
per night
26 May - 27 May
Quality Inn Lexington -Horse Park
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.

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Winchester has a good selection of restaurants. Make sure you have time to check out the coffee shops and shopping during your trip.

How many holiday rentals are there in Winchester?

Expedia has 7 holiday 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.

Recent reviews of Winchester properties
Expedia verified reviews