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.
Apartment in Richmond
4.96 out of 5 average rating, 285 reviewsEast 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
Farm stay in Winchester
4.93 out of 5 average rating, 101 reviewsLenMar 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
Train in Lawrenceburg
4.98 out of 5 average rating, 250 reviewsBourbon 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
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Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Apartment in Winchester
4.93 out of 5 average rating, 96 reviewsThe River House Floor 2 Getaway, w/a river view.
Aug 10 – 17
Loft in Winchester
4.98 out of 5 average rating, 56 reviewsStylish Loft Historic Downtown 2Bdrm Winchester KY
Oct 19 – 26
Farm stay in Winchester
4.85 out of 5 average rating, 41 reviewsThe Winchester Retreat
Sep 10 – 17
Farm stay in Winchester
4.88 out of 5 average rating, 41 reviewsRenovated historic home on working cattle farm
Mar 19 – 26
Home in Winchester
5.0 out of 5 average rating, 12 reviewsCute 2 Story Home in Winchester
Sep 27 – Oct 4
Apartment in Mount Sterling
4.94 out of 5 average rating, 48 reviewsHistoric 2-Bedroom Apartment in Downtown
Jul 12 – 19
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
Home in Richmond
4.91 out of 5 average rating, 22 reviewsNear to EKU; discounts to 10%
Nov 12 – 19
Tiny home in Richmond
5.0 out of 5 average rating, 9 reviewsTiny Home; Mini Farm Getaway
Apr 4 – 11
Cabin in Waco
5.0 out of 5 average rating, 53 reviewsStunning Cedar Cabin, Hot Tub, Amazing Views!
Jun 11 – 18
Loft in Mount Sterling
4.93 out of 5 average rating, 27 reviewsDowntown Loft Apartment, Relaxing Retreat
Apr 2 – 9
Cabin in Irvine
4.95 out of 5 average rating, 57 reviewsSunset Ridge ~ Rustic & Tranquil 100-Acre Getaway!
Jan 27 – Feb 3
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 |
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