Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

The Winchester

The Winchester
Winchester
8.4 out of 10, Very good, (7 reviews)
"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "
United States
Karissa A.
The price is AU$442
includes taxes & fees
8 June - 9 June
The Winchester

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

4 Bed 3 bath clean , spacious all brick home , welcome families and work groups
Winchester
9.8 out of 10, Exceptional, (9 reviews)
"Very homey place to stay! Nice neighborhood!"
United States
Tim T.
The price is AU$442
includes taxes & fees
8 June - 9 June
4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5
Stanton
9.4 out of 10, Exceptional, (15 reviews)
"Fun for the family!"
United States
Jennifer
The price is AU$189
includes taxes & fees
9 June - 10 June
Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

Conveniently Located ~ WiFi ~ Central Heat & Air.

Conveniently Located ~ WiFi ~ Central Heat & Air.
Stanton
9.8 out of 10, Exceptional, (50 reviews)
"Very nice area and quiet. Outside of the home looked a bit rough. Inside was clean and organized with everything you would need to be comfortable. The owner was very responsive and informative. It was a very fun stay. Stanton is a beautiful town with lots of outdoor activities. I highly recommend booking here at the Towner. We will be booking again next year."
United States
Darren
The price is AU$302
includes taxes & fees
21 June - 22 June
Conveniently Located ~ WiFi ~ Central Heat & Air.

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,912 reviews)
"Great place to stay, they have a place to eat, trails to walk and lots of nice people around."
United States
Coty jay
The price is AU$177
includes taxes & fees
14 June - 15 June
Natural Bridge State Resort Park

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, (107 reviews)
"This was a wonderful location and a delightfully cozy cabin for a couple or a solo stay. Might very well stay here again in the future."
United States
Jason H.
The price is AU$275
includes taxes & fees
11 June - 12 June
Sunset Ridge Cabin – Hilltop Sunset Views Near Red River Gorge

Quaint, heavily forested cabin, mountain valley view.

Quaint, heavily forested cabin, mountain valley view.
Slade
8.2 out of 10, Very good, (33 reviews)
"Beautiful little cabin"
United States
Ryan W.
The price is AU$298
includes taxes & fees
8 June - 9 June
Quaint, heavily forested cabin, mountain valley view.

"Rocky Top" - Cozy RRG Cabin

"Rocky Top" - Cozy RRG Cabin
Stanton
9.2 out of 10, Wonderful, (14 reviews)
"Great location "
United States
Zach M.
The price is AU$342
includes taxes & fees
8 June - 9 June
"Rocky Top" - Cozy RRG Cabin

Briar Patch Cabin RRG: Firepit, Sunset, WIFI

Briar Patch Cabin RRG: Firepit, Sunset, WIFI
Stanton
10.0 out of 10, Exceptional, (46 reviews)
"The cabin was beautiful. We had a peaceful stay with everything we needed."
United States
Jennifer B.
The price is AU$305
includes taxes & fees
8 June - 9 June
Briar Patch Cabin RRG: Firepit, Sunset, WIFI

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)
"This is a unique property, it feels like stepping into history. It is well maintained, clean and comfortable but not your average stay! "
United States
Jennie C.
The price is AU$258
includes taxes & fees
9 June - 10 June
Unique Stay in a 1907 Log Cabin on The Kentucky River

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, (6 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 AU$254
includes taxes & fees
8 June - 9 June
Dappled Grey Cabin with hot tub at Red River Gorge

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, (130 reviews)
"Wonderful stay! Everything was clean and view was great. Thanks for a great stay! "
United States
Abby H.
The price is AU$406
includes taxes & fees
9 June - 10 June
THIS IS THE ONE! SHIPPING CONTAINER CABIN-VIEW-WIFI-NATURAL BRIDGE-NADA TUNNEL

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, (69 reviews)
"Excellent stopover. "
United States
Robert W.
The price is AU$331
includes taxes & fees
9 June - 10 June
1800’s Historical Log Cabin near I-75 Interstate

Mountain Memories Cabin

Mountain Memories Cabin
Stanton
10.0 out of 10, Exceptional, (76 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 AU$278
includes taxes & fees
18 June - 19 June
Mountain Memories Cabin

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (35 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is AU$260
includes taxes & fees
8 June - 9 June
Mountaintop Cottage

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveller
The price is AU$481
includes taxes & fees
10 June - 11 June
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub
Stanton
10.0 out of 10, Exceptional, (7 reviews)
"Yes, I brought my tiny dog and she loved it there as much as we did! "
United States
Kimberly J.
The price is AU$461
includes taxes & fees
8 June - 9 June
Red River Gorge Cozy Glamping Tent for 4 • Heated, Fire Pit & Hot Tub

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi

Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Stanton
8.6 out of 10, Excellent, (61 reviews)
"Very cozy and an amazing stay!"
United States
Sam P.
The price is AU$472
includes taxes & fees
18 June - 19 June
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi

"Cardinal Crest" - Overlook Dome 002 in RRG

"Cardinal Crest" - Overlook Dome 002 in RRG
Stanton
10.0 out of 10, Exceptional, (6 reviews)
"Very quiet, cozy and a nice place to come back to after a long day of physical activity! "
United States
Gregory L.
"Cardinal Crest" - Overlook Dome 002 in RRG

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
Stanton
9.6 out of 10, Exceptional, (23 reviews)
"Beautiful cabin and property, very quiet and surely secluded. Very clean and decorated, stocked well with cooking utensils. We will definitely make plans to visit again!"
United States
Kevin S.
The price is AU$344
includes taxes & fees
8 June - 9 June
Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.
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

Find out more about Winchester

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, 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 favourite 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 depend 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 AU$177 per night. Entering your travel dates in the search wizard might find you 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.

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

Near Kentucky State Horse Park 💛The Yalla House🚪 🏇🏼Horse & Bourbon Central🥃: This holiday home rental outside of Winchester is located in a rural location, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Winchester?

Expedia has 5 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

Community Park and The Holler are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Wiseman Park and Winchester Traveling Trail 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.