Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Richmond

4.96 out of 5 average rating, 285 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.

Apr 28 – May 5

R2,075 ZAR per night
Guest favorite

Farm stay in Winchester

4.93 out of 5 average rating, 101 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.

Jun 7 – 14

R1,793 ZAR per night
Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 250 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Aug 30 – Sep 6

R2,881 ZAR per night

Popular amenities for Winchester vacation rentals

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 vacation rentals in Winchester

Guest favorite

Apartment in Winchester

4.93 out of 5 average rating, 96 reviews

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

Aug 10 – 17

R1,700 ZAR per night
Guest favorite

Loft in Winchester

4.98 out of 5 average rating, 56 reviews

Stylish Loft Historic Downtown 2Bdrm Winchester KY

Oct 19 – 26

R2,906 ZAR per night
Superhost

Farm stay in Winchester

4.85 out of 5 average rating, 41 reviews

The Winchester Retreat

Sep 10 – 17

R2,139 ZAR per night
Guest favorite

Farm stay in Winchester

4.88 out of 5 average rating, 41 reviews

Renovated historic home on working cattle farm

Mar 19 – 26

R2,537 ZAR per night
Guest favorite

Home in Winchester

5.0 out of 5 average rating, 12 reviews

Cute 2 Story Home in Winchester

Sep 27 – Oct 4

R3,511 ZAR per night
Guest favorite

Apartment in Mount Sterling

4.94 out of 5 average rating, 48 reviews

Historic 2-Bedroom Apartment in Downtown

Jul 12 – 19

R2,071 ZAR per night
Guest favorite

Farm stay in Winchester

5.0 out of 5 average rating, 51 reviews

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

Jul 10 – 17

R2,544 ZAR per night
Guest favorite

Home in Richmond

4.91 out of 5 average rating, 22 reviews

Near to EKU; discounts to 10%

Nov 12 – 19

R1,672 ZAR per night
Guest favorite

Tiny home in Richmond

5.0 out of 5 average rating, 9 reviews

Tiny Home; Mini Farm Getaway

Apr 4 – 11

R2,370 ZAR per night
Guest favorite

Cabin in Waco

5.0 out of 5 average rating, 53 reviews

Stunning Cedar Cabin, Hot Tub, Amazing Views!

Jun 11 – 18

R2,835 ZAR per night
Superhost

Loft in Mount Sterling

4.93 out of 5 average rating, 27 reviews

Downtown Loft Apartment, Relaxing Retreat

Apr 2 – 9

R1,608 ZAR per night
Guest favorite

Cabin in Irvine

4.95 out of 5 average rating, 57 reviews

Sunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!

Jan 27 – Feb 3

R2,288 ZAR per night

Quick stats about vacation 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

R947 ZAR before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Clark County
  5. Winchester