Holiday houses in Winchester

4.92 out of 5 average rating, 151 reviews

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

4.98 out of 5 average rating, 262 reviews

Cabin in McKee

The Cabin on Panther Branch

Drive down Kentucky scenic highway 89 South just 9 miles south of McKee. The cabin is newly built and set back in a secluded area with a small creek running right beside the cabin and a larger creek just across the road. The Cabin on Panther Branch is a perfect place to come fish and kayak on the creek. Bring your ATV’s, side by side or dirt bikes and enjoy miles and miles of riding in S-Tree Tower in the Daniel Boone National Forest. We don’t think you will be disappointed with your stay.

4.97 out of 5 average rating, 367 reviews

Cabin in McKee

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

4.93 out of 5 average rating, 199 reviews

Guesthouse in Winchester

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

4.93 out of 5 average rating, 222 reviews

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

4.91 out of 5 average rating, 812 reviews

Home in Winchester

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

4.91 out of 5 average rating, 261 reviews

Guesthouse in Lexington

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

4.97 out of 5 average rating, 119 reviews

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm is 5 minutes to DT Winchester close to Lexington Quick access to I64 close to I75 **Check-in & SAVE~Mon.-Fri. ~June 23,24,25,26,27 Centrally located: Eateries & Historical Sites Lexington 20min State Parks Meadow Green Music Park 20min Keeneland 30.4mi. Kentucky Horse Park 30min Red River Gorge 35min Ark Encounter 45min Creation Museum 1hr 30min ~Home is surrounded by our family farm EST. 1803 at the beginning of Scenic Rt.15 So much to see & do

4.99 out of 5 average rating, 130 reviews

Tiny home in Stanton

Tiny Cabin At The Pond

Welcome to peace and quiet! If seclusion is what you're searching for, then you have found the place! Located on a hobby farm beside of a stocked fishing pond, it's as much of a destination as it is an accommodation. The closest neighbors are 3 friendly donkeys that love to greet guests at the fence for attention and ear rubs. Fishing poles and donkey treats are provided to round out your stay. We're 20 scenic minutes to Slade or Stanton and 25 to Mount Sterling.

Superhost

4.82 out of 5 average rating, 114 reviews

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

4.82 out of 5 average rating, 576 reviews

Cabin in Lexington

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

4.89 out of 5 average rating, 151 reviews

Apartment in Winchester

The River House Floor 2 Getaway, w/a river view.

Enjoy the spectacular views of the Kentucky River from this second floor studio. Located within an easy walk of hiking trails. After your hike (or whenever, you are on vacation), visit the Waterfront Grill or Hall’s on the River. They offer dining, bar, and seasonal outdoor seating. They are about a half mile down the road from the cottage. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby.

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Other great holiday rentals in Winchester

4.95 out of 5 average rating, 84 reviews

Cabin in Paris

1791 Cabin on Historic Horse Farm

AmandaRating, 5 stars1 week ago

Jessica was a wonderful host; kind and thoughtful. The cabin was exactly as described. It was clean and comfortable. Waking up to the chirping birds and seeing the horses grazing was fantastic.

Apartment in Winchester

4.66 out of 5 average rating, 110 reviews

2nd Story Historic Downtown 2 BR w Modern Comforts

NicholasRating, 5 stars3 weeks ago

As we walked down the sidewalk to the little red door on main street. we were greeted by the sounds of laughter and children playing. as the sun crested the city sky, we embarked on our journey upstairs. we had some trouble with the locking mechanism, but as spider-man rescues mary jane, so to did joel come to our rescue and he saved us from the dangerous world outside. joel is an outstanding host with a very kind and gentle voice. i knew from the second i met joel that there is only here and now! As we entered the apartment we were greeted with scents of vanilla and lavender. as the moon rose and we got settled for bedtime, we listened to the sounds of birds chirping and watched the beautiful night sky dance above our heads. as heaven and earth collided we drifted off to sleep in the most comfortable memory foam beds. joel is an incredible human being who possessed the professionalism of a wall street billionaire with childlike enthusiasm. joel has changed my life for the better.

4.9 out of 5 average rating, 67 reviews

Renovated historic home on working cattle farm

NicoleRating, 5 stars2 weeks ago

Beautiful farm and location! The stay could not have been more perfect! We really appreciated the recommendation book that the host left for us. Thank you for an amazing weekend :)

4.88 out of 5 average rating, 205 reviews

Home in Mount Sterling

THE DOLLY - Cozy, Bright Home in Historic Downtown

RobertRating, 5 stars1 month ago

We've stayed at The Dolly before, and it's one of our favorite places! Lot's of space, very comfortable bed, and extra clean. Highly recommend!

4.9 out of 5 average rating, 84 reviews

Home in Paris

Misfit Farm

VictoriaRating, 5 stars1 week ago

I cannot say enough good things about Misfit Farm! The location was so serene, the movie room was awesome for our family movie night, and the garden tub was so relaxing. But our favorite part was getting to meet all the animals on the farm! Tim let my seven-year-old son feed the goats and let me bottle-feed Buttercup, the baby cow. Our favorite farm friends were Rusty, the bull and Shadow, the cat - so friendly! We sipped tea on the front porch at night while we watched fireflies, and then we got a heavenly night's sleep on the comfy beds. This place is amazing - we will definitely be back.

4.86 out of 5 average rating, 66 reviews

Cabin in Clay City

It’s the perfect Silver Lining!

Heather ReneeRating, 5 stars6 days ago

We stayed in the smaller cabin, which was perfect for the 2 of us. I wish the kitchen had better lighting which is my only complaint. and won't prevent me from staying again. I will stay here again. Sonya was very friendly. The area was very private. Her dogs are so friendly.

Apartment in Winchester

4.85 out of 5 average rating, 33 reviews

Whimsical Winchester Apartment!

MichelleRating, 5 stars1 month ago

We had a wonderful short stay at this property. We had everything we needed. Joseph was so kind in his communication! He stayed up late until we arrived to make sure we didn't have any issues.