Vacation rentals in Winchester

4.93 out of 5 average rating, 161 reviews

A wooden sign reading 'LENMAR FARM Est. 2019' is prominently displayed on a green metal gate. The sign showcases a natural wood grain, and the background features an open field with scattered trees and horse jumps.

Farm stay in Winchester

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ 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.

4.96 out of 5 average rating, 134 reviews

A spacious living area features a comfortable sectional sofa accompanied by a recliner. A patterned area rug covers the floor, and a coffee table stands nearby. A fireplace is set against a white brick wall, with decorative shelves holding various items above.

Home in Richmond

Near to EKU; discounts to 10%

Located 5 minutes from I-75. Newly renovated basement apartment perfect for solo travelers, friends or couples and is pet friendly. Take it easy at this country setting and enjoy the pool. Convenient to EKU, stay after a day at Keeneland, exploring the Bourbon Trial, concerts or just a peaceful and relaxing getaway. Available small hot tub on request. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

4.83 out of 5 average rating, 212 reviews

A cozy bedroom features blue walls adorned with butterfly decor and soft lighting. A queen bed is dressed with a floral comforter and surrounded by an inviting area rug. A small couch and side table add to the room's charm, with doors leading to additional living spaces.

Home in Mount Sterling

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

4.93 out of 5 average rating, 205 reviews

A traditional bedroom showcases a four-poster bed with a patterned comforter. A decorative lamp sits on a bedside table, and a vintage console table with a plant adds a touch of greenery. Natural light enters the room through the open door, enhancing the serene ambiance.

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.

4.87 out of 5 average rating, 103 reviews

A tranquil outdoor pool is surrounded by a smooth deck, featuring blue planters at each corner. Lush greenery and trees create a natural backdrop, while the Kentucky River is visible beyond the pool area. The setting offers a relaxing ambiance for outdoor enjoyment.

Cottage in Winchester

Life is Better On The River

Make lasting memories at this unique and family-friendly cottage on the Kentucky River. Enjoy nature at its best, along with all the comforts of home. Guests return year after year. * WiFi is sometimes unreliable. It connects via satellite, as this is the only option available in our neighborhood. WIFI Riverstar, Pw 12345678 This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations, but occasional cobwebs happen.

4.97 out of 5 average rating, 126 reviews

A rustic wooden box labeled 'Farmhouse' holds jars filled with daisies and assorted natural elements, set against a green field. A cow stands nearby, framed by soft evening light, with trees in the background, creating a peaceful farm scene.

Farm stay in Winchester

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm is 5 minutes to DT Winchester close to Lexington 5min. access to I64; 15min. to I75/I 64 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 *All guests must be registered to see total price of your stay before booking

4.91 out of 5 average rating, 838 reviews

The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.

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.

4.94 out of 5 average rating, 104 reviews

A serene bedroom features a spacious bed dressed in a navy blue coverlet and decorative pillows. Natural light filters through two large windows adorned with blinds, illuminating the warm wood flooring. A small decorative bench sits beside the bed, complemented by a nightstand and a framed piece of art on the wall.

Apartment in Winchester

The Carriage Inn - 1-bdrm apt in historic downtown

Centrally located in historic downtown Winchester with views of the county courthouse. Apartment is upstairs in a building that was originally used as a carriage repair shop. It is within walking distance to lots of unique shops and restaurants and the Bluegrass Heritage Museum. Walk or drive to the Farmers Market (seasonal) on historic Depot Street on Saturday mornings. The Red River Gorge/Natural Bridge area is 40 minutes east. Lexington is a short 20-30 minutes west.

5 out of 5 average rating, 214 reviews

A private entrance is displayed, featuring a white door with glass panels above. Wood railing with modern iron designs surrounds a small porch area, creating an inviting entrance. The exterior wall is clad in gray siding, complemented by a stylish light fixture.

Guest suite in Gainesway

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!

4.81 out of 5 average rating, 130 reviews

Farm stay in Winchester

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, 592 reviews

The living area features rustic log walls contrasted by a bright ceiling. A cozy sectional sofa faces a wooden coffee table and a small desk with a TV. Two armchairs are positioned beside a colorful area rug, while natural light filters through multiple windows.

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)

4.98 out of 5 average rating, 122 reviews

A comfortable living room is presented, featuring two plush armchairs and a spacious sectional sofa with cushions. A coffee table is positioned centrally, while a stone fireplace adds a rustic element. Large windows provide natural light, framing views of the surrounding nature.

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 vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winchester

5 out of 5 average rating, 8 reviews

A charming farmhouse exterior is highlighted by a welcoming front porch and gabled roof. Surrounding greenery complements the well-maintained landscaping, with spacious lawns providing an inviting setting. The home is illuminated by soft lighting during twilight, creating a peaceful atmosphere.

Home in Paris

The Tisbury House

Apartment in Winchester

4.5 out of 5 average rating, 22 reviews

The Perch - NEW / Downtown!

A spacious home exterior is visible, featuring a two-story structure with a wooden balcony and an entrance door. The green yard is surrounded by trees, and a driveway leads to a covered parking area below the balcony. Power lines are discreetly visible in the background.

Home in Winchester

4.68 out of 5 average rating, 25 reviews

The Winchester 2

4.94 out of 5 average rating, 16 reviews

A white, two-story house is framed by lush greenery and brick pathways. An inviting front porch is adorned with a decorative railing. A garden with a fountain and flowering plants enhances the exterior, creating a charming and welcoming entrance.

Farm stay in Paris

Carriage House

4.97 out of 5 average rating, 29 reviews

A living room features hardwood flooring and a cozy seating area with a light-colored couch and an armchair. A wooden coffee table sits in front of a stone fireplace, and a television is mounted above the mantel. A potted plant adds greenery to the space.

Home in Lexington

Cozy and Welcoming Condo

5 out of 5 average rating, 18 reviews

A modern cabin exterior is framed by tall trees, showcasing a combination of wood and large glass windows. A wooden deck extends from the cabin, providing outdoor seating. The surrounding lush green forest enhances the natural integration of the structure.

Cabin in Rosslyn

Skogen - A Modern Masterpiece in the Trees

Shipping container in Lexington

The exterior of the tiny home features a welcoming entrance with a lit door and two potted plants on either side. A wooden chair and side table are positioned on a deck made of wooden planks. Soft lighting enhances the ambiance as twilight approaches.

4.8 out of 5 average rating, 5 reviews

Shipping Container Cabin - Tuck Jr