Places to stay in Winchester

A small pony is depicted grazing in a grassy area, surrounded by two cats resting nearby. The fenced pasture in the background enhances the rural setting, with green panels visible behind the animals.

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.

4.97 out of 5 average rating, 366 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, 198 reviews

A charming exterior view of the house features a welcoming porch with decorative plants and an American flag. A concrete pathway leads from the sidewalk to the entrance, flanked by manicured lawn areas and mature trees providing shade.

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.

4.99 out of 5 average rating, 282 reviews

The cozy cabin is set against a vibrant green landscape, featuring large trees and an inviting pond. A stone fire pit is surrounded by several outdoor chairs, creating a tranquil space for relaxation. A deck extends from the cabin, offering views of the serene surroundings.

Cabin in McKee

Peaceful getaway for couples - Hemlock Haven LLC

*Please read entire listing and rules* Step away from fast paced life to experience true relaxation at our tiny cabin, situated in the one stop light town with some of the country's best internet! Located in the heart of the Daniel Boone National Forest, Hemlock Haven LLC has been customized to be a nature lovers paradise. Our cabin is in a fairly remote area, but we do have a few local convenience stores and restaurants where you'll find plenty of hospitality and country cooking!

4.91 out of 5 average rating, 808 reviews

A small outdoor seating area features two bright red chairs and a round table on a pebbled surface. A lush green lawn extends into the distance, framed by trees and a wooden fence, creating a peaceful outdoor retreat.

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.

4.97 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~June 10,11,12,16,17;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

4.91 out of 5 average rating, 259 reviews

Two gray Adirondack chairs are positioned around a circular stone firepit, which features a glowing fire at its center. Surrounding the area are trees and lush greenery, providing a natural backdrop for outdoor relaxation.

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.

4.99 out of 5 average rating, 120 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

A clean bathroom space includes a toilet and a storage shelf with magazines. A cozy couch is visible in the adjacent area, contributing to a relaxed atmosphere. Natural light enters through a nearby window, enhancing the overall brightness of the room.

4.81 out of 5 average rating, 110 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, 573 reviews

The image shows a stone plaque embedded in a textured concrete wall, featuring the year '1907' etched into its surface. Ivy leaves are partially visible, growing against the wall and adding a touch of greenery to the historical element.

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, 150 reviews

A tranquil river scene at dusk is depicted, with dark silhouettes of trees lining the shore. A reflection of the fading light creates a serene atmosphere on the water's surface. Subtle colors blend in the sky, transitioning from deep blue to soft pastels.

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.

4.97 out of 5 average rating, 115 reviews

A young alpaca with a fluffy, light tan coat is captured front and center. Its large, expressive eyes and small mouth create a gentle appearance. A larger companion alpaca is partially visible in the background, alongside the rustic wooden barn and patches of straw on the ground.

Cottage in Clay City

Scenic views, farm fun in peaceful modern cottage

A family-friendly farm that offers opportunities for couples, families or small groups to create special memories. Our farm is also the perfect place for unique family adventures, family reunions, retreats, parties of any type and intimate weddings - all in an idyllic country setting (events charged separately). We offer educational tours and introductions to our animals for guests that are interested.

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Popular amenities for Winchester places to stay

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Other great vacation rentals in Winchester

4.95 out of 5 average rating, 82 reviews

Cabin in Paris

1791 Cabin on Historic Horse Farm

RachelRating, 5 stars1 week ago

Enjoyed getting to stay in cabin and explore the property at Houstondale. Loved all the Horses there and also the pool area was very nice. Jessica was an Awesome host and made us feel right at home, very accessible and friendly! Very Beautiful location and would recommend to any guest if they are looking for a nice getaway.

The wooden staircase features polished steps and a decorative railing, highlighted by a vintage lantern resting on the newel post. The warm tones of the wood enhance the historic character, while a soft yellow wall provides a gentle backdrop to the elegant design.

Home in Winchester

5 out of 5 average rating, 4 reviews

College Park Getaway

MikaelRating, 5 stars3 weeks ago

Had an issue with the AC not working and it was fixed very quickly! Nice house with good beds.

The historic courthouse features a prominent clock tower with a gold dome atop its white façade. Nearby, the street is lined with charming buildings showcasing the downtown area's character. An American flag stands in front of the courthouse, contributing to the local atmosphere.

Apartment in Winchester

4.66 out of 5 average rating, 109 reviews

2nd Story Historic Downtown 2 BR w Modern Comforts

JamRating, 5 stars1 month ago

Joel is truly what an Airbnb Host should be. Her delivers a pristine clean place and is Extremely Responsive! Just note that your GPS will not lead you to the entrance. But, that’s not Joel’s fault.

4.93 out of 5 average rating, 28 reviews

Place to stay in Irvine

Stay at The World Famous Holla Holler in Downtown

BeverlyRating, 5 stars2 days ago

Such an amazing find. This was a great family bonding experience. We took advantage of the performance area and brought instruments and had so much fun the TV wasn’t turned on once. Very clean and the beds were very comfortable. A Mexican and pizza restaurant are right across the street. The host is very responsive and nice. Highly recommend.

4.9 out of 5 average rating, 67 reviews

Renovated historic home on working cattle farm

NicoleRating, 5 stars1 week 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!