Holiday Rentals in Winchester
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Holiday Rentals in Winchester

Natural Bridge State Resort Park

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!

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!

Cabin for two with an awesome view

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

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!

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

Mountain Memories Cabin

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

Mountaintop Cottage

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

Unique, Cozy Stay near Red River Gorge

Tranquil Getaway in the Woods ~ Sunset Ridge
Other types of properties in Winchester you may be interested in

Baymont by Wyndham Winchester
Holiday Accommodation Winchester
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Winchester are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Winchester itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Winchester holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Winchester, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Winchester with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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