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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, (1605)
"Room was clean and staff was amazing "
Natural Bridge State Resort Park

Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (121)
"We enjoyed the cabin it was a super cute place. My only complaint was when we arrived the couch was torn up and there was cookies all over it. Other than that it was a great place, close to everything you want to experience "
The price is NZ$488
includes taxes & fees
8 July - 9 July
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (147)
"Was an amazing stay"
The price is NZ$388
includes taxes & fees
28 July - 29 July
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

9.6 out of 10, Exceptional, (288)
"The cabin is lovely! Everything was clean and all the extras provided made this a comfortable stay. "
The price is NZ$347
includes taxes & fees
21 July - 22 July
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

9.4 out of 10, Exceptional, (71)
"We needed a short convenient layover in the middle of a trip and this worked perfectly. "
The price is NZ$359
includes taxes & fees
17 July - 18 July
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

8.8 out of 10, Excellent, (17)
"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!!

Cabin for two with an awesome view

9.4 out of 10, Exceptional, (20)
"Great place and great location."
The price is NZ$486
includes taxes & fees
2 July - 3 July
Cabin for two with an awesome view

Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

9.6 out of 10, Exceptional, (49)
"Wonderful cabin! Great communication with the owner. The interior is up to date and well appointed. I would stay there again."
The price is NZ$519
includes taxes & fees
2 July - 3 July
Ursa Major Cabin - 10 mins from Natural Bridge State Park, Red River Gorge

Mountain Memories Cabin

10.0 out of 10, Exceptional, (37)
"Our stay was great and very relaxing. The host responded to all communication very quickly. Definitely would stay again. "
The price is NZ$358
includes taxes & fees
9 July - 10 July
Mountain Memories Cabin

Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!

9.0 out of 10, Wonderful, (156)
"Beautiful cabin in a terrific location. We enjoyed all the amenities!! Thanks for a lovely stay."
The price is NZ$498
includes taxes & fees
7 July - 8 July
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!

Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

10.0 out of 10, Exceptional, (22)
"We really enjoyed the place and will be back in the future. "
The price is NZ$241
includes taxes & fees
8 July - 9 July
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

9.2 out of 10, Wonderful, (80)
"Well managed clean perfect location for child out. "
The price is NZ$455
includes taxes & fees
8 July - 9 July
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (11)
"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$316
includes taxes & fees
14 July - 15 July
Mountaintop Cottage

Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

10.0 out of 10, Exceptional, (13)
"Bathroom was SO CLEAN! Beautiful location, will come back! "
The price is NZ$235
includes taxes & fees
22 July - 23 July
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (58)
"Cabin was the perfect getaway and so peaceful."
The price is NZ$243
includes taxes & fees
7 July - 8 July
Tranquil Getaway in the Woods ~ Sunset Ridge

Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!

8.4 out of 10, Very good, (120)
"This cabin is great! The wrap around deck is awesome for hanging out in the evenings, and the loft bedroom was super cool."
The price is NZ$350
includes taxes & fees
9 July - 10 July
Hot Tub - Tiny A-Frame Cabin - Haven at the Red - Red River Gorge, Kentucky!

Whispering Woods • Modern Cabin w/ HOT TUB

9.8 out of 10, Exceptional, (10)
"My family stayed here for a long weekend getaway. We went cave kayaking and hiking. We loved the location. My kids loved the hot tub and loft beds. "
Whispering Woods • Modern Cabin w/ HOT TUB

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

9.4 out of 10, Exceptional, (19)
"We had a great time staying here. Barely noticed the highway noise. "
The price is NZ$418
includes taxes & fees
8 July - 9 July
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!

"ENDLESS VIEW" Red River Gorge/Natural Bridge- New Construction!! Dog Friendly!!

10.0 out of 10, Exceptional, (53)
"Our stay at the endless view property was excellent. The owners are very responsive to any and all questions and have created a beautiful place to spend with friends and family. Would not hesitate to book again if vacationing in the area "
"ENDLESS VIEW" Red River Gorge/Natural Bridge- New Construction!! Dog Friendly!!

Unique, Cozy Stay near Red River Gorge

8.0 out of 10, Very good, (4)
"Love it ❤️"
The price is NZ$230
includes taxes & fees
8 July - 9 July
Unique, Cozy Stay near 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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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?

WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!: This holiday home rental outside of Winchester is located in the mountains, and has a selection of games, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Winchester?

Expedia has 8 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.