Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

Apartment in Richmond

4.96 out of 5 average rating, 294 reviews

East Unit Apartment in Historic Tenant House on Main Street

Head past the custom front-door painting and into an interior with original hardwood flooring. Standouts include a remote-control fireplace and subway-tiled kitchen with stainless steel appliances. A wood stove adds a warm glow to the shared patio. This 1920's shotgun-style four unit apartment building has been completely restored with all modern amenities. The Tenant House has a rich history on Main Street in downtown Richmond. Guests have access to all shared spaces I will be available 24/7 for contact via text, call, email, or in person. Information about the surrounding area and the unit will be provided. Walk to the latest downtown venues and jog round nearby parks from this location, directly across from the Richmond Visitors Center. Eastern Kentucky University is also convenient for here, while many places to eat and drink are on the doorstep.

Jul 1 – 8

G$24,510 GYD per night

Guest favorite

Farm stay in Winchester

4.94 out of 5 average rating, 108 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.

Jul 19 – 26

G$20,290 GYD per night

Guest favorite

Cabin in McKee

4.99 out of 5 average rating, 136 reviews

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.

Mar 25 – Apr 1

G$23,386 GYD per night

Guest favorite

Home in Berea

4.92 out of 5 average rating, 639 reviews

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

Apr 5 – 12

G$22,796 GYD per night

Guest favorite

Home in Mount Sterling

4.96 out of 5 average rating, 143 reviews

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!

Jun 26 – Jul 3

G$16,751 GYD per night

Guest favorite

Guesthouse in Winchester

4.95 out of 5 average rating, 160 reviews

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.

Jul 29 – Aug 5

G$16,947 GYD per night

Guest favorite

Apartment in Winchester

4.93 out of 5 average rating, 74 reviews

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.

May 3 – 10

G$20,295 GYD per night

Guest favorite

Home in Winchester

4.91 out of 5 average rating, 676 reviews

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 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.

Jul 20 – 27

G$12,783 GYD per night

Guest favorite

Guesthouse in Winchester

4.98 out of 5 average rating, 176 reviews

Escape and unwind in the country

Relax and unwind in the country! Close to Lexington, Red River Gorge, Pilot Knob and Natural Bridge with easy access to the Mountain Parkway. We now have Wi-Fi!! Pets are welcome but we request that dogs are either crated or not left unattended. There is a $25 pet cleaning fee. Our guest house has a fully equipped kitchen, washer/dryer, queen size Sleep Number Bed, queen size sleeper sofa, and patio with gas grill. An air mattress is available by request.

Aug 22 – 29

G$16,024 GYD per night

Guest favorite

Farm stay in Irvine

4.96 out of 5 average rating, 114 reviews

Beautiful cabin, creek, woods, horse farm.

Bella Vista sits on 175 acres of pasture, woods, trails and a beautiful creek in the Red Lick Valley. Once a large-scale horse farm we currently have only four pasture puffs who you will see grazing around the cabin. Enjoy beautiful sunsets, walk the creek looking for Kentucky agates, geodes, explore the trails, or just take solace in the peace and quiet of the cabin. We bought the farm in 2020 and are in the process of bringing it back to its glory days.

Jul 9 – 16

G$26,875 GYD per night

Superhost

Cabin in Lexington

4.81 out of 5 average rating, 448 reviews

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)

Mar 5 – 12

G$17,827 GYD per night

Guest favorite

Barn in Lexington

4.94 out of 5 average rating, 294 reviews

Stay with our horses and goats on a private farm

Lovely and private studio barn apartment in super safe neighborhood. Stay with our horse and goats on 12 private acres, minutes from downtown Lexington. Hiking trails around property, and just minutes to several state parks. Three miles to 75 and 64, and 15 minutes to downtown Lexington, the Kentucky Horse Park, UK campus, and 10 minutes to the Hamburg area of Lexington full of restaurants, sports bars, and movie theaters. 50 amp EV charging station

Dec 11 – 18

G$18,685 GYD per night