Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite

Flat in Richmond

4.97 out of 5 average rating, 287 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.

24–31 May

€ 109 per night

Guest favourite

Farm stay in Winchester

4.93 out of 5 average rating, 105 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.

7–14 Jun

€ 96 per night

Superhost

Farm stay in Winchester

4.86 out of 5 average rating, 43 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 relax in our luxurious jetted tub, 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.

19–26 Jan

€ 113 per night

Guest favourite

Loft in Winchester

4.98 out of 5 average rating, 57 reviews

Stylish Loft Historic Downtown 2Bdrm Winchester KY

New York style loft meets historic renovation—Central Kentucky. Meet charming Winchester. Under hr. to Keeneland race track, Kentucky Horse Park, & the spectacular Red River Gorge/Natural Bridge. Lexington 30 min. Paris, Georgetown, Richmond & Berea close too. Many local, small businesses-restaurants, brewery, distillery, shops, antiques, flea markets, & historical sites! Unit is on the second floor—may not be right for all abilities. Public, street parking. See our lovely town renovation.

23 Feb – 2 Mar

€ 172 per night

Guest favourite

Home in Mount Sterling

4.96 out of 5 average rating, 138 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!

31 Aug – 7 Sep

€ 85 per night

Guest favourite

Cabin in Berea

4.92 out of 5 average rating, 167 reviews

A Happy Place Cabin with magical views!

A cabin and experience like no other in Berea. Enjoy the smell of cedar, sounds of the country, amazing views of the mountains and magical sunsets! Relax in our cozy all cedar cabin that sits on a 37 acre property. Fish in the large pond, swing on the porch, and cook dinner outside on the Blackstone griddle. Located just 5 miles from town, it is close enough to find great dining options and visit all that Berea has to offer, yet far enough away to provide serene tranquility and peace.

27 Feb – 6 Mar

€ 126 per night

Guest favourite

Guest house in Winchester

4.95 out of 5 average rating, 158 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.

10–17 Aug

€ 85 per night

Guest favourite

Flat in Winchester

4.93 out of 5 average rating, 73 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.

31 Jan – 7 Feb

€ 102 per night

Guest favourite

Home in Winchester

4.91 out of 5 average rating, 672 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.

23–30 Jun

€ 62 per night

Guest favourite

Guest house in Winchester

4.98 out of 5 average rating, 174 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.

19–26 May

€ 77 per night

Superhost

Cabin in Lexington

4.81 out of 5 average rating, 441 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)

27 Jan – 3 Feb

€ 96 per night

Guest favourite

Barn in Lexington

4.93 out of 5 average rating, 292 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

1–8 Jan

€ 99 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Winchester holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winchester's top sights

Kroger3 locals recommend

Winchester Peddlers Mall3 locals recommend

Blue Isle Home-Style Restaurant and Bar3 locals recommend

Engine House Pizza Pub8 locals recommend

Malco Winchester Cinema3 locals recommend

The Daily Grind4 locals recommend

Other great holiday rentals in Winchester

Guest favourite

Flat in Winchester

4.92 out of 5 average rating, 99 reviews

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

1–8 Oct

€ 95 per night

Guest favourite

Farm stay in Winchester

4.88 out of 5 average rating, 41 reviews

Renovated historic home on working cattle farm

11–18 Jun

€ 145 per night

Guest favourite

Home in Winchester

5.0 out of 5 average rating, 13 reviews

Cute 2 Story Home in Winchester

4–11 Dec

€ 191 per night

Guest favourite

Home in Irvine

5.0 out of 5 average rating, 45 reviews

Pauline's Paradise

19–26 Apr

€ 81 per night

Guest favourite

Loft in Winchester

5.0 out of 5 average rating, 12 reviews

Hanna’s 1,400 SQ FT Downtown Royal Retreat Loft

21–28 Jan

€ 156 per night

Guest favourite

Farm stay in Winchester

5.0 out of 5 average rating, 52 reviews

2Rm*Farm Cottage*Comfy King * DT Winchester 5 min.

26 Sep – 3 Oct

€ 165 per night

Guest favourite

Cabin in Waco

5.0 out of 5 average rating, 56 reviews

Stunning Cedar Cabin, Hot Tub, Amazing Views!

17–24 Jun

€ 161 per night

Guest favourite

Tiny home in Richmond

5.0 out of 5 average rating, 11 reviews

Tiny Home; Mini Farm Getaway

5–12 Jul

€ 133 per night

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Quick stats about holiday rentals in Winchester

Total rentals	10 properties
Wifi availability	10 properties include access to wifi
Rentals with dedicated workspaces	10 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Total number of reviews	1.2K reviews
Nightly prices starting at	€ 47 before taxes and fees

Holiday rentals in Winchester

Top-rated holiday rentals in Winchester

Flat in Richmond

Farm stay in Winchester

Farm stay in Winchester

Loft in Winchester

Home in Mount Sterling

Cabin in Berea

Guest house in Winchester

Flat in Winchester

Home in Winchester

Guest house in Winchester

Cabin in Lexington

Barn in Lexington

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Winchester holiday rentals

Stay near Winchester's top sights

Other great holiday rentals in Winchester

Flat in Winchester

Farm stay in Winchester

Home in Winchester

Home in Irvine

Loft in Winchester

Farm stay in Winchester

Cabin in Waco

Tiny home in Richmond

Quick stats about holiday rentals in Winchester

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore