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Winchester Holiday Rentals

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Holiday Rentals in Winchester

Cabin in Slade

3.5 star property
8.6 out of 10, Excellent, (1783)
"Front desk staff was super nice, room was perfect as we were hiking and needed a place to relax and get some sleep! "
United States
Kathy
Natural Bridge State Resort Park

Cabin in Slade

9.6 out of 10, Exceptional, (200)
"It was a very relaxing stay. I would recommend this place to everyone. "
United States
Robert S.
Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area

Camping in Stanton

10.0 out of 10, Exceptional, (24)
"Will definitely stay again. Next time will be with our kiddos. "
United States
Alexandra
The price is AU$208
includes taxes & fees
8 Dec - 9 Dec
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Cabin in Stanton

9.6 out of 10, Exceptional, (308)
"Cabin was wonderful. Great communication before and during arrival and was so incredibly clean. Definitely recommend!"
United States
Todd
Hot Tub & WiFi - Cozy Canopy - Red River Gorge KY

Cabin in Stanton

10.0 out of 10, Exceptional, (345)
"Fantastic place! We loved our visit! "
United States
Christe H.
The price is AU$443
includes taxes & fees
8 Dec - 9 Dec
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!

Cabin in Stanton

9.0 out of 10, Wonderful, (26)
"Great cabin close to hiking trails great places to eat "
United States
Zachary N.
Pet-Friendly Retreat by Rock Wall w/ Hot Tub

Cabin in Stanton

9.6 out of 10, Exceptional, (35)
"Nice place, very quiet. We enjoyed the quiet mornings on the deck watching the sun come up. "
United States
Mike V.
Cabin for two with an awesome view

Cabin in Stanton

9.8 out of 10, Exceptional, (28)
"Nice clean place to stay"
United States
Logan R.
The price is AU$334
includes taxes & fees
9 Dec - 10 Dec
"Valley View Lodge" - Modern Spacious Stay RRG - Slade

Cabin in Stanton

2.0 star property
7.0 out of 10, Good, (7)
"Nice calm and nice cabin and was cozy I had fun for my birthday overall great experience "
United States
MainSlime
The price is AU$270
includes taxes & fees
11 Dec - 12 Dec
Hot Tub! Tiny Cabin Retreat near RRG

Cabin in Stanton

10.0 out of 10, Exceptional, (153)
"We really enjoyed staying here! Hopefully we’ll be back some day!"
United States
Donna K.
The price is AU$366
includes taxes & fees
8 Dec - 9 Dec
UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!

Cabin in Irvine

10.0 out of 10, Exceptional, (54)
"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$411
includes taxes & fees
8 Dec - 9 Dec
Secluded & Tranquil Cabin ~ Near Red River Gorge

Cottage in Slade

7.4 out of 10, Good, (10)
"Me and my girlfriend had a great time enjoy the area around were we were staying and had a great time and the people their were nice"
United States
William
Unique, Cozy Stay near Red River Gorge

Cabin in Slade

9.0 out of 10, Wonderful, (87)
"beautiful stay! "
United States
Brookeanne H.
Hot Tub & WiFi - Romantic Hideaway

Cabin in Irvine

10.0 out of 10, Exceptional, (83)
"The stay was awesome! My husband asked if we could stay another night. It is so quiet and peaceful here. Awesome experience!"
United States
Marsha
The price is AU$227
includes taxes & fees
4 Jan - 5 Jan 2026
Tranquil Getaway in the Woods ~ Sunset Ridge

Cabin in Stanton

9.2 out of 10, Wonderful, (134)
"The cabin was cozy and comfortable. We enjoyed the porch, side deck, and hot tub. Perfect location to get to great hikes. The manager was super responsive. The Wi-Fi wasn’t working. They tries to fix it and gave us a small refund when it couldn’t re corrected. "
United States
Elizabeth D.
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn

Cabin in Stanton

9.6 out of 10, Exceptional, (161)
"Cabin was adorable. It was the perfect getaway for my husband and me. "
United States
Danielle
Hot Tub, WiFi & Pet-Friendly - Pilot Point

Cabin in Slade

9.6 out of 10, Exceptional, (56)
"Great place and location."
United States
Jim H.
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!

Cabin in Slade

8.8 out of 10, Excellent, (164)
"We stayed over night on a short trip to the gorge. Cabin was very clean and looked just like the pictures. We also enjoyed the hot tub!"
United States
Heather H.
Gorgeous View Cabin - in Red River Gorge, KY

Camping in Stanton

9.8 out of 10, Exceptional, (28)
"It was amazing peaceful great view comfortable beds. "
United States
James F.
The price is AU$208
includes taxes & fees
8 Dec - 9 Dec
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Cabin in Stanton

9.0 out of 10, Wonderful, (66)
"Great weekend "
United States
Josh A.
Hot Tub, WiFi & Pool Table - Mountain Rose
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$208 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?

Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location: This holiday home rental outside of Winchester is located in the city centre, and has a fireplace, a patio 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.

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. Cassell Creek 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.