Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

7.0 out of 10, Good, (4 reviews)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
United States
Maeve R.
River Relaxation - Calm Riverfront Home in Winchester Kentucky
10.0 out of 10, Exceptional, (24 reviews)
"Will definitely stay again. Next time will be with our kiddos. "
United States
Alexandra
The price is AU$205
includes taxes & fees
22 Jan - 23 Jan
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
9.8 out of 10, Exceptional, (47 reviews)
"A great place to stay while exploring the area"
United States
lisa s.
The price is AU$256
includes taxes & fees
22 Jan - 23 Jan
Conveniently Located ~ WiFi ~ Central Heat & Air.
10.0 out of 10, Exceptional, (128 reviews)
"Wonderful stay!! So close to red river gorge! Was packed with anything you would need for a great stay!!! "
United States
Julie S.
The price is AU$324
includes taxes & fees
22 Jan - 23 Jan
Relaxing, cozy cabin in the heart of the Red River Gorge!
3.5 star property
8.6 out of 10, Excellent, (1,795 reviews)
"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."
United States
Kimberly
Natural Bridge State Resort Park
3.0 star property
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$390
includes taxes & fees
22 Jan - 23 Jan
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
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$264
includes taxes & fees
22 Jan - 23 Jan
Dappled Grey Cabin with hot tub at Red River Gorge
2.0 star property
8.0 out of 10, Very good, (11 reviews)
"Nice calm and nice cabin and was cozy I had fun for my birthday overall great experience "
United States
MainSlime
The price is AU$267
includes taxes & fees
23 Jan - 24 Jan
Hot Tub! Tiny Cabin Retreat near RRG
8.2 out of 10, Very good, (28 reviews)
"Cabin was good but other cabins are close cabin was very comfortable road to cabin is very steep but doable "
United States
Terry
The price is AU$307
includes taxes & fees
24 Jan - 25 Jan
Quaint, heavily forested cabin, mountain valley view.

Cottage in Stanton

Mountaintop Cottage
2.0 star property
10.0 out of 10, Exceptional, (27 reviews)
"I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again."
United States
Jessica H.
The price is AU$290
includes taxes & fees
31 Jan - 1 Feb
Mountaintop Cottage
2.0 star property
7.2 out of 10, Good, (5 reviews)
"Overall, great stay! The tiny house looked just like the photos and the hot tub was added relaxation. Lots of hiking options in the area that we were able to explore!The only heads up would be that the drive back to the cabin is gravel, bumpy, and mainly uphill…so if you don’t have a vehicle that can handle it, it could be tricky. Our Jeep made it just fine though!"
United States
Jaimie K.
The price is AU$272
includes taxes & fees
22 Jan - 23 Jan
Hot Tub! Tiny House Retreat in the Woods
9.8 out of 10, Exceptional, (15 reviews)
"Overall the cabin was very nice. There were some minor maintenance issues, such as the electric fireplace not working and the remotes for the tv needing batteries, but it was a great cabin. We enjoyed our stay. "
United States
Anonymous traveller
The price is AU$518
includes taxes & fees
22 Jan - 23 Jan
Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit
10.0 out of 10, Exceptional, (13 reviews)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
United States
Kenetra F.
The price is AU$261
includes taxes & fees
22 Jan - 23 Jan
Peregrine Cabin - Off the Grid, hike-in cabin
10.0 out of 10, Exceptional, (58 reviews)
"Loved every bit of this precious space, very close to lots of different activities and tons of stuff to do inside the cabin as well for lazy days "
United States
Ryan S.
The price is AU$388
includes taxes & fees
22 Jan - 23 Jan
Secluded & Tranquil Cabin ~ Near Red River Gorge
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great. It was a nice place to relax for a weekend. The kitchen is fully equipped so bring some groceries and make your own meals."
United States
Randy S.
The price is AU$419
includes taxes & fees
22 Jan - 23 Jan
Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi
9.2 out of 10, Wonderful, (13 reviews)
"Great place to stay! Super close to RRG and the DBBB. Also just a few minutes for Miguel’s for the BEST pizza!"
United States
Mallory H.
The price is AU$308
includes taxes & fees
26 Jan - 27 Jan
"Rocky Top" - Cozy RRG Cabin
10.0 out of 10, Exceptional, (18 reviews)
"It was wonderful and cozy! So conveniently located to all the good hiking spots. Would return for another stay (:"
United States
Maya J.
The price is AU$367
includes taxes & fees
22 Jan - 23 Jan
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!
10.0 out of 10, Exceptional, (118 reviews)
" Cozy, private and clean cabin with a lovely view from the hot tub."
United States
kelly l.
The price is AU$360
includes taxes & fees
22 Jan - 23 Jan
The DEN Shipping Container Cabin-HotTub!-High Speed WiFi!-Great View & Location!
8.4 out of 10, Very good, (32 reviews)
"We had a beautiful stay. This house has a wonderful home feel! It was clean and had everything we needed. We will be back! "
United States
Corrie S.
The price is AU$266
includes taxes & fees
3 Feb - 4 Feb
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay. Location was amazing for our trip!"
United States
Deanna E.
The price is AU$346
includes taxes & fees
2 Feb - 3 Feb
Amazing Beds, Fast WiFi - Walk to EKU & Downtown Venues - 5 minutes to I-75
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$197 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?

Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.: This holiday home rental outside of Winchester is located on a river, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 6 holiday rentals for your stay in Winchester.

What can I see and do in Winchester?

College Park and GRCHS Baseball Field are a couple of scenic spots to enjoy the outdoors, whereas Bluegrass Heritage Museum is one of the cultural attractions. Southwind Golf Course and Winchester Opera House 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.