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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1653)
"Very convenient and beautiful views! "
Natural Bridge State Resort Park

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

9.4 out of 10, Exceptional, (123)
"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 €261
includes taxes & fees
13 Aug - 14 Aug
Hot Tub & WiFi - Intimate Cabin - Snuggle Inn - Red River Gorge, Kentucky!

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

9.6 out of 10, Exceptional, (295)
"The cabin is lovely! Everything was clean and all the extras provided made this a comfortable stay. "
The price is €180
includes taxes & fees
12 Aug - 13 Aug
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!

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

9.0 out of 10, Wonderful, (158)
"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!"
Hot Tub & WiFi - Gorgeous View Cabin - Large Family Cabin in Red River Gorge, Kentucky!

Cabin for two with an awesome view

9.4 out of 10, Exceptional, (25)
"We had a great time celebrating our anniversary. "
The price is €257
includes taxes & fees
25 Aug - 26 Aug
Cabin for two with an awesome view

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

9.6 out of 10, Exceptional, (150)
"Was an amazing stay"
The price is €213
includes taxes & fees
10 Aug - 11 Aug
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!

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

9.8 out of 10, Exceptional, (23)
"We really enjoyed the place and will be back in the future. "
The price is €127
includes taxes & fees
14 Aug - 15 Aug
Furnished Glamping Tent/King Bed/Access to the Red River - Dancing Deer - #6

Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!

8.8 out of 10, Excellent, (104)
"Great stay"
The price is €251
includes taxes & fees
19 Aug - 20 Aug
Hot Tub, WiFi, No Pet Fee - Beary Cozy - Romantic Cabin in Red River Gorge, Kentucky!

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

9.0 out of 10, Wonderful, (82)
"Well managed clean perfect location for child out. "
The price is €243
includes taxes & fees
12 Aug - 13 Aug
Hot Tub & WiFi - Romantic Hideaway - Wooded Retreat near Red River Gorge, Kentucky!

Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!

9.0 out of 10, Wonderful, (60)
"This place is not only amazing to stay at, it’s so close to everything. So many amazing trails, and plenty of options for food. The pictures really don’t do this place justice. It was in perfect shape, and the hot tub was an amazing touch after a long day of hiking. "
The price is €248
includes taxes & fees
19 Aug - 20 Aug
Hot Tub, WiFi & Pool Table - Perfect Cabin Retreat - Mountain Rose - Getaway to Red River Gorge, KY!

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

9.6 out of 10, Exceptional, (41)
"Cozy, attractive cottage near to all the natural attractions and hiking. "
Tanzanite-- The "GEM" with a Hot Tub & WiFi!!

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

8.6 out of 10, Excellent, (19)
"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!

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

9.2 out of 10, Wonderful, (76)
"My family had a pleasant time at Throw'n Shade. It was a quick trip to get outdoors at the Gorge, grab some pizza, then a evening at the cabin. The location is beautiful, nice view of a valley in the spring with no close neighbors. Just enough for what we were looking for."
The price is €192
includes taxes & fees
19 Aug - 20 Aug
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!

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

9.8 out of 10, Exceptional, (42)
"We had a really relaxing stay with our dogs! They really enjoyed the yard & we enjoyed the pool! We will be back again! Thank you again!"
Morning View Ranch- Red River Gorge- Indoor Pool open March-Nov. Pet friendly.

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

8.6 out of 10, Excellent, (20)
"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!!

Mountain Memories Cabin

10.0 out of 10, Exceptional, (43)
"The layout was perfect for two families. "
The price is €197
includes taxes & fees
11 Aug - 12 Aug
Mountain Memories Cabin

Wildwood Cabin RRG, Hot tub-private hikes nearby

9.2 out of 10, Wonderful, (15)
"Wife and I stayed a couple of days as a getaway. We had a great time. Owner was easy to communicate with. Recommend the cabin."
Wildwood Cabin RRG, Hot tub-private hikes nearby

Tranquil Getaway in the Woods ~ Sunset Ridge

9.8 out of 10, Exceptional, (63)
"Nice little place tucked into the woods. Good proximity to interesting areas."
The price is €130
includes taxes & fees
18 Aug - 19 Aug
Tranquil Getaway in the Woods ~ Sunset Ridge

Upscale Shipping Container in the Woods of Red River Gorge | Hot Tub | Private

10.0 out of 10, Exceptional, (132)
"This was the perfect spot for our weekend getaway. We had the feeling of being remote, but within driving range of Natural Bridge and our multiple visits to Miguel’s Pizza! Unit was very cozy and host was very welcoming! Would definitely stay again!"
The price is €196
includes taxes & fees
10 Aug - 11 Aug
Upscale Shipping Container in the Woods of Red River Gorge | Hot Tub | Private

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

10.0 out of 10, Exceptional, (15)
"Beautiful place, great accommodations and we loved the evening fires next to the river."
The price is €127
includes taxes & fees
20 Aug - 21 Aug
Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1
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

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.