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Winchester Holiday Rentals

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Holiday Rentals in Winchester

Natural Bridge State Resort Park
3.5 star property
8.6 out of 10, Excellent, (1742)
"We had a wonderful stay. Everyone was friendly and helpful and the cottage was spacious, well kept, beautiful and walkable to all attractions. "
United States
Sarah Ann
Natural Bridge State Resort Park
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
10.0 out of 10, Exceptional, (13)
"It fit our family of 13 very well. We hiked near by during the day and played games and used the hot tub at night! Very clean and had everything we needed. We would definitely stay here again. "
United States
Matt M.
Hot Tub, Fire Pit, WiFi, EV Charger | Biggie cabin near Red River Gorge, KY!
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
10.0 out of 10, Exceptional, (12)
"This place was different than any other place I’ve stayed at; so cool! It was very comfortable and super clean. The setting is perfect for a quiet getaway, but the location is close to everything. We had a great stay! "
United States
Josh B.
The price is AU$399
includes taxes & fees
26 Oct - 27 Oct
ESCAPE!-In The Woods of Red River Gorge!-Hot Tub-High Speed WIFI!-Outdoor Shower
Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area
9.6 out of 10, Exceptional, (197)
"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
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!
10.0 out of 10, Exceptional, (335)
"Location was great for exploring the Red River Gorge. Hot tub was perfect after long days of hiking!"
United States
Steven S.
The price is AU$467
includes taxes & fees
29 Oct - 30 Oct
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!
UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!
10.0 out of 10, Exceptional, (147)
"We really enjoyed staying here! Hopefully we’ll be back some day!"
United States
Donna K.
The price is AU$385
includes taxes & fees
4 Nov - 5 Nov
UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
10.0 out of 10, Exceptional, (22)
"Such an amazing get away "
United States
Laqueena
The price is AU$223
includes taxes & fees
5 Nov - 6 Nov
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
"Valley View Lodge" - Modern Spacious Stay RRG - Slade
9.8 out of 10, Exceptional, (26)
"Cozy cabin. Enjoyed the hot tub. Close "
United States
Shastine
The price is AU$605
includes taxes & fees
6 Nov - 7 Nov
"Valley View Lodge" - Modern Spacious Stay RRG - Slade
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
8.4 out of 10, Very good, (22)
"This place was the best little get away.... Very cute and very clean....There were some things that I had to address, but it was a really nice stay for me and my Penny. I will definitely book this little quaint getaway again"
United States
fell b.
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
Quaint, heavily forested cabin, mountain valley view.
2.0 star property
8.0 out of 10, Very good, (23)
"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$319
includes taxes & fees
23 Oct - 24 Oct
Quaint, heavily forested cabin, mountain valley view.
Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action
10.0 out of 10, Exceptional, (4)
"Cabin was perfect for our anniversary weekend! Spent nights out by the fire pit and loved having a hot tub. This cabin truly felt like our home away from home. The host was excellent and very polite to work with. Definitely adding this place to our favorite places to stay in the gorge!"
United States
Evan M.
Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action
CREEKSIDE CABIN
7.0 out of 10, Good, (2)
"Cute and cozy and very clean."
United States
Sheena P.
The price is AU$315
includes taxes & fees
3 Nov - 4 Nov
CREEKSIDE CABIN
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
9.6 out of 10, Exceptional, (50)
"This little cabin was super cute and charming. It had everyhting we needed and for a short weekend stay. The local restaurants were great ans views amazing!"
United States
Kelly S.
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
9.8 out of 10, Exceptional, (26)
"It was amazing peaceful great view comfortable beds. "
United States
James F.
The price is AU$223
includes taxes & fees
5 Nov - 6 Nov
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
8.8 out of 10, Excellent, (53)
"Very nice stay. We loved the covered porch with the swing and hot tub. All we could see around us was trees. Very Peaceful."
United States
Melissa
Secluded cabin in Red River Gorge with a Hot Tub and wi-fi
Quaint old fashioned cabin, Loft, Grill, Fire Pit!
8.0 out of 10, Very good, (22)
"We loved the cabin it was clean , cool and was exactly what we were looking for !! Will definitely book again. "
United States
Sabrina
Quaint old fashioned cabin, Loft, Grill, Fire Pit!
Cabin for two with an awesome view
9.6 out of 10, Exceptional, (33)
"Had a super relaxing and fun stay for our two year wedding anniversary. Beautiful views and peaceful, quiet atmosphere. Loved the lights and record player in the cabin. "
United States
Kirsten W.
Cabin for two with an awesome view
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
9.8 out of 10, Exceptional, (45)
"The pool was awesome!!! We spent hours in the pool. The house is bigger than it looks in the pictures and had everything we needed. Close to town with all the shopping you need but felt like it was out in the country."
United States
Karen R.
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
Mountaintop Cottage
2.0 star property
10.0 out of 10, Exceptional, (21)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
United States
Brandylynn M.
The price is AU$303
includes taxes & fees
22 Oct - 23 Oct
Mountaintop Cottage
Relaxing, cozy cabin in the heart of the Red River Gorge!
10.0 out of 10, Exceptional, (121)
"Amazing!!!"
United States
Carla M.
Relaxing, cozy cabin in the heart of the Red River Gorge!
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$223 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?

Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge: This holiday home rental outside of Winchester offers a patio, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 College 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 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.