Photo by Hyelsinta

Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1715)
"Beautiful and quiet place to stay."
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)
"Biggie cabin was perfect, and great location! Would absolutely stay there again! "
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, (9)
"This is a great property we used for a long weekend. Quiet and private yet not a long drive to hiking trails and restaurants. Owner is easy to work with and very kind. Appreciate the use of your property."
The price is NZ$471
includes taxes & fees
1 Oct - 2 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, (195)
"Convenient location and great stay!"
Luxurious Cabin Across From The Red River Gorge, In The Natural Bridge Area

UPSCALE Shipping Container Cabin-Private-High Speed WIFI!-Hot Tub!-In The Woods!

10.0 out of 10, Exceptional, (145)
"We really enjoyed staying here! Hopefully we’ll be back some day!"
The price is NZ$460
includes taxes & fees
1 Oct - 2 Oct
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, (20)
"Such an amazing get away "
The price is NZ$248
includes taxes & fees
1 Oct - 2 Oct
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

"Valley View Lodge" - Modern Spacious Stay RRG - Slade

9.6 out of 10, Exceptional, (24)
"Great location for visiting Red River Gorge. We happily will stay there again!"
The price is NZ$594
includes taxes & fees
1 Oct - 2 Oct
"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 cottage was such a great place to come back to after a long day of hiking and exploring Red River Gorge. Super cute in & outside with a beautiful landscape. We also had visits from a local cat every morning and night and he was so extremely sweet and made the trip all the more better."
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!

10.0 out of 10, Exceptional, (331)
"Location was great for exploring the Red River Gorge. Hot tub was perfect after long days of hiking!"
The price is NZ$555
includes taxes & fees
19 Oct - 20 Oct
The ORIGINAL Shipping Container Cabin in RRG-High Speed WiFi!-Hot Tub!-View!

Quaint, heavily forested cabin, mountain valley view.

2.0 star property
8.0 out of 10, Very good, (22)
"Everything was great. The hiking and rocks around the property were awesome. "
The price is NZ$352
includes taxes & fees
2 Oct - 3 Oct
Quaint, heavily forested cabin, mountain valley view.

Quaint old fashioned cabin, Loft, Grill, Fire Pit!

8.2 out of 10, Very good, (21)
"We loved the cabin it was clean , cool and was exactly what we were looking for !! Will definitely book again. "
Quaint old fashioned cabin, Loft, Grill, Fire Pit!

CREEKSIDE CABIN

10.0 out of 10, Exceptional, (1)
"Cute and cozy and very clean."
The price is NZ$394
includes taxes & fees
1 Oct - 2 Oct
CREEKSIDE CABIN

Delightfully secluded 1 bed and a loft for extra space. TV and DVD player.

9.0 out of 10, Wonderful, (22)
"We had a Wonderful Relaxing Peaceful Time at This Cottage It Was Very Nice!."
Delightfully secluded 1 bed and a loft for extra space. TV and DVD player.

Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action

10.0 out of 10, Exceptional, (3)
"This was the most beautiful cabin we have ever stayed in! Everything was clean and the kitchen is well stocked with essentials. We had the most relaxing last minute getaway. Shane checked on us several times to assure our stay was great. The cabin is very peaceful and the huge windows accentuate the outdoor beauty making you feel part of the forest."
Scandanavian Cabin-Hot Tub-EV Charger-Fire Pit-Close to All RRG Action

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (18)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
The price is NZ$334
includes taxes & fees
1 Oct - 2 Oct
Mountaintop Cottage

Tanzanite-- The "GEM" with a Hot Tub & WiFi!!

9.8 out of 10, Exceptional, (47)
"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!"
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, (25)
"It was amazing peaceful great view comfortable beds. "
The price is NZ$248
includes taxes & fees
1 Oct - 2 Oct
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Peregrine Cabin - Off the Grid, hike-in cabin

10.0 out of 10, Exceptional, (12)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
Peregrine Cabin - Off the Grid, hike-in cabin

Relaxing, cozy cabin in the heart of the Red River Gorge!

10.0 out of 10, Exceptional, (119)
"We really enjoyed our stay. The evenings were relaxing hanging out on the porch listening to the rain and nature. Very clean and had everything we needed. Nice and close to a lot of trails and natural attractions. "
Relaxing, cozy cabin in the heart of the Red River Gorge!

Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.

9.8 out of 10, Exceptional, (44)
"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."
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

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 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 NZ$248 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.

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

This bungalow is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.: This holiday home rental outside of Winchester is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge to make your meal-planning easier.

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.