Title: Winchester Vacation Home Rentals from CA $242: Search Top Private Vacation Homes for Rent | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation homes

![Exterior](https://images.trvl-media.com/lodging/113000000/112560000/112559200/112559158/4a2d8b78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/113000000/112560000/112559200/112559158/d9d2fe36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112560000/112559200/112559158/a7a50533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112560000/112559200/112559158/4fd23e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Relaxation - Calm Riverfront Home in Winchester Kentucky

[](https://www.expedia.ca/Lexington-Hotels-River-Relaxation-3-King-Beds-In-Winchester.h112559158.Hotel-Information)

Winchester

7.0/10

Good

(4 reviews)

"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Maeve R.

CA $143

CA $432 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Lexington-Hotels-River-Relaxation-3-King-Beds-In-Winchester.h112559158.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122640000/122639300/122639291/827a70c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122640000/122639300/122639291/799967eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122640000/122639300/122639291/fcf7bfd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122640000/122639300/122639291/df8e3ba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canoe Believe It at The Ridge

[](https://www.expedia.ca/Slade-Hotels-Canoe-Believe-It-At-The-Ridge.h122639291.Hotel-Information)

Powell County

10/10

Exceptional

(1 review)

"Great place! Would stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rachel B.

CA $145

CA $274 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Slade-Hotels-Canoe-Believe-It-At-The-Ridge.h122639291.Hotel-Information)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122110000/122108000/122107929/888eb40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122110000/122108000/122107929/35f9f31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122110000/122108000/122107929/d0630c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/123000000/122110000/122108000/122107929/6e7005d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub

[](https://www.expedia.ca/Stanton-Hotels-Tiny-Home-In-The-Heart-Of-Red-River-Gorge.h122107929.Hotel-Information)

Stanton

10/10

Exceptional

(2 reviews)

"Perfect small cozy cabin for a couple get away. Thank you. We really enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carrie F.

CA $111

CA $276 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stanton-Hotels-Tiny-Home-In-The-Heart-Of-Red-River-Gorge.h122107929.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543758/3f494dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543758/cb291f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543758/654f5cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543758/010904f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peregrine Cabin - Off the Grid, hike-in cabin

[](https://www.expedia.ca/Stanton-Hotels-Peregrine-Cabin-Off-The-Grid.h74543758.Hotel-Information)

Stanton

10/10

Exceptional

(13 reviews)

"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kenetra F.

CA $143

CA $242 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stanton-Hotels-Peregrine-Cabin-Off-The-Grid.h74543758.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/123000000/122780000/122772100/122772004/a28fef61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, stovetop](https://images.trvl-media.com/lodging/123000000/122780000/122772100/122772004/5b8d7d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122780000/122772100/122772004/w1024h609x0y0-b1754cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/123000000/122780000/122772100/122772004/0363517d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Thoroughbred Retreat

[](https://www.expedia.ca/Lexington-Hotels-The-Thoroughbred-Retreat.h122772004.Hotel-Information)

Lexington

10/10

Exceptional

(1 review)

"Unit was clean, well stocked, easy to access. Perfect place for us to lay our heads each night and enough space to not be on top of each other. The hot water tank kept up great. Parking spot assignment is super close making unloading and loading a breeze. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly B.

CA $151

CA $254 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Lexington-Hotels-The-Thoroughbred-Retreat.h122772004.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/124000000/123050000/123046300/123046267/6a27941c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123050000/123046300/123046267/d4086da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123050000/123046300/123046267/a064a374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123050000/123046300/123046267/9c045dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom house in Lexington and close to many area attractions.

[](https://www.expedia.ca/Lexington-Hotels-Spacious-4-Bedroom-House-In-Lexington-And-Close-To-Many-Area-Attractions.h123046267.Hotel-Information)

Lexington

10/10

Exceptional

(2 reviews)

"Great location and great hosts!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Josh A.

CA $143

CA $510 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Lexington-Hotels-Spacious-4-Bedroom-House-In-Lexington-And-Close-To-Many-Area-Attractions.h123046267.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89150000/89142600/89142517/b79aa01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89150000/89142600/89142517/7139b2ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89150000/89142600/89142517/c85ce014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89142600/89142517/b6cb0f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### My Old Kentucky Home

[](https://www.expedia.ca/Lexington-Hotels-My-Old-Kentucky-Home.h89142517.Hotel-Information)

Lexington

10/10

Exceptional

(27 reviews)

"Cool property, with a great location. Owner had great communication."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $108

CA $352 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Lexington-Hotels-My-Old-Kentucky-Home.h89142517.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/1160c1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/c8c32e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/3076f388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/3f08204d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

[](https://www.expedia.ca/Lexington-Hotels-This-House-Is-A-2-Bedroom.h83782041.Hotel-Information)

Georgetown

8.4/10

Very good

(32 reviews)

"We had a beautiful stay. This house has a wonderful home feel! It was clean and had everything we needed. We will be back! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Corrie S.

CA $111

CA $246 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Lexington-Hotels-This-House-Is-A-2-Bedroom.h83782041.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112760000/112759200/112759116/80644fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/113000000/112760000/112759200/112759116/158b6bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112760000/112759200/112759116/6ef2056c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112760000/112759200/112759116/b0bb4a71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Kentucky Stone House

[](https://www.expedia.ca/Lexington-Hotels-Charming-Kentucky-Stone-House.h112759116.Hotel-Information)

Lexington

10/10

Exceptional

(4 reviews)

"My wife and daughter stayed and said it was nice, clean, and easy to navigate, too. They would stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justin M.

CA $97

CA $338 total

includes taxes & fees

Feb 2 - Feb 3

[](https://www.expedia.ca/Lexington-Hotels-Charming-Kentucky-Stone-House.h112759116.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89150000/89143100/89143070/b2aa296f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89150000/89143100/89143070/3f1fe383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/90000000/89150000/89143100/89143070/f1679c90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89150000/89143100/89143070/w1794h1200x0y0-33718bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-bedroom in Lexington

[](https://www.expedia.ca/Lexington-Hotels-Cozy-1-Bedroom-In-Lexington.h89143070.Hotel-Information)

Lexington

9.2/10

Wonderful

(10 reviews)

"The property was clean and well kept, the location is perfect and communication was immediate. I will definitely rent again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Becky S.

CA $88

CA $310 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Lexington-Hotels-Cozy-1-Bedroom-In-Lexington.h89143070.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101500000/101490300/101490281/76f969b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101500000/101490300/101490281/57a1d5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101500000/101490300/101490281/e20bcbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101500000/101490300/101490281/f749f023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 50 Shades of Slade- Pet friendly, WiFi, Hot tub, Firepit

[](https://www.expedia.ca/Stanton-Hotels-WiFi.h101490281.Hotel-Information)

Stanton

9.4/10

Exceptional

(28 reviews)

"This property was amazing! Clean, affordable, easy check in, easy to navigate to and so close to everything we wanted to do during our stay! Great place and great owners! Thank you for helping us make memories!!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

nicolle h.

CA $159

CA $328 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stanton-Hotels-WiFi.h101490281.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/125000000/124280000/124277500/124277439/1dd0cd3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124280000/124277500/124277439/34fca4cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124280000/124277500/124277439/4a6dafea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/125000000/124280000/124277500/124277439/cde3fed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1-bedroom ranch house in Georgetown on 10 acres with horse paddock.

[](https://www.expedia.ca/Lexington-Hotels-Cozy-1-Bedroom-Ranch-House-In-Georgetown-On-10-Acres-With-Horse-Paddock.h124277439.Hotel-Information)

Georgetown

10/10

Exceptional

(1 review)

"I stayed here recovering from surgery. The convenience and comfort of the house helped me to relax. Mitzi was extremely accommodating and the perfect host! I would highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charlotte F.

CA $122

CA $241 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Lexington-Hotels-Cozy-1-Bedroom-Ranch-House-In-Georgetown-On-10-Acres-With-Horse-Paddock.h124277439.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100030000/100029100/100029055/3a879d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/101000000/100030000/100029100/100029055/d0d90639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100030000/100029100/100029055/9e89123a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/101000000/100030000/100029100/100029055/d0c68f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Barndo/ATV Parking/Private Access to Red River

[](https://www.expedia.ca/Stanton-Hotels-New-BarndoATV-ParkingPrivate-Access-To-Red-River.h100029055.Hotel-Information)

Stanton

10/10

Exceptional

(3 reviews)

"We stayed here for one night and wish we could have stayed longer. The property was incredible. Very thoughtfully decorated, spacious, and has everything you need plus more. Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephen S.

CA $162

CA $448 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stanton-Hotels-New-BarndoATV-ParkingPrivate-Access-To-Red-River.h100029055.Hotel-Information)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108010000/108010000/108009943/f77e8527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108010000/108010000/108009943/fac40583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/109000000/108010000/108010000/108009943/7a187d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108010000/108010000/108009943/248095b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Luxe/Hot Tub/Private Bar/ 12 Min to Horse Park

[](https://www.expedia.ca/Lexington-Hotels-The-LuxeHot-TubPrivate-Bar-12-Min-To-Horse-Park.h108009943.Hotel-Information)

Georgetown

10/10

Exceptional

(6 reviews)

"A beautiful place! Super convenient to the Kentucky Horse Park. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Niamh O.

CA $202

CA $683 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Lexington-Hotels-The-LuxeHot-TubPrivate-Bar-12-Min-To-Horse-Park.h108009943.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114590000/114589100/114589014/cedf8b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114590000/114589100/114589014/a94adfbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114590000/114589100/114589014/214fc807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114590000/114589100/114589014/0e0a3141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious King Suite | Game Room | Patio | Firepit

[](https://www.expedia.ca/Lexington-Hotels-Spacious-King-Suite-Game-Room-Patio-Firepit.h114589014.Hotel-Information)

Georgetown

9.8/10

Exceptional

(10 reviews)

"Very nice and clean home. And was equipped with what we needed. Would stay again if in that area."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pamela L.

CA $174

CA $440 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Lexington-Hotels-Spacious-King-Suite-Game-Room-Patio-Firepit.h114589014.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96640000/96630600/96630548/8e0105d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/97000000/96640000/96630600/96630548/f0ccb463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/97000000/96640000/96630600/96630548/8b36cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96640000/96630600/96630548/34550cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly Bluegrass Retreat w/ Fenced Yard

[](https://www.expedia.ca/Lexington-Hotels-Kentuckys-Finest-Pet-Friendly.h96630548.Hotel-Information)

Georgetown

9.4/10

Exceptional

(29 reviews)

"Cute quaint neighborhood, big back yard space, host very responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenny M.

CA $97

CA $285 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Lexington-Hotels-Kentuckys-Finest-Pet-Friendly.h96630548.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/117000000/116240000/116232600/116232568/cedd8898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116240000/116232600/116232568/8853c051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116240000/116232600/116232568/d368db0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116240000/116232600/116232568/a5736129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 4-bedroom home, close to Downtown/UK

[](https://www.expedia.ca/Lexington-Hotels-Beautiful-4-Bedroom-Home.h116232568.Hotel-Information)

Lexington

10/10

Exceptional

(3 reviews)

"We had a great stay at this property. The house was clean and 100% ready to go. Great location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan H.

CA $162

CA $403 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Lexington-Hotels-Beautiful-4-Bedroom-Home.h116232568.Hotel-Information)

![TV, DVD player](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543754/9a06d2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543754/37ff14e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543754/b374d386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74550000/74543800/74543754/150f905e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kim's Retreat: 3-BR Cabin w/ Hot Tub near Natural Bridge & Red River Gorge

[](https://www.expedia.ca/Stanton-Hotels-Kims-Retreat-Cabin-Ridgetop-Cabin-Close-To-Red-River-Gorge.h74543754.Hotel-Information)

Stanton

9.0/10

Wonderful

(18 reviews)

"Very nice. Much more secluded than I thought it would be and a little further from civilization, but if that is what you're looking for it's perfect. Be aware that there is a cliff close by so if you have kids, let them know not to go near it! Great communication with the owners. Hot tub was amazing. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessica B.

CA $140

CA $348 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stanton-Hotels-Kims-Retreat-Cabin-Ridgetop-Cabin-Close-To-Red-River-Gorge.h74543754.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103430000/103428000/103427953/1d21c484.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/104000000/103430000/103428000/103427953/a506f956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/104000000/103430000/103428000/103427953/f85eca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103430000/103428000/103427953/f07ae6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 💙Modern Downtown with Parking - Keeneland - Horse Park

[](https://www.expedia.ca/Lexington-Hotels-Modern-Downtown-With-Parking-Keeneland-Horse-Park.h103427953.Hotel-Information)

Lexington

9.8/10

Exceptional

(26 reviews)

"Enjoyed our stay. Location was great. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nancy P.

CA $149

CA $381 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Lexington-Hotels-Modern-Downtown-With-Parking-Keeneland-Horse-Park.h103427953.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/125000000/124470000/124466800/124466713/73132227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124470000/124466800/124466713/83d15d2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124470000/124466800/124466713/a183dfe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124470000/124466800/124466713/2ef7f1e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hunting Lodge in the City

[](https://www.expedia.ca/Mount-Sterling-Hotels-Cozy-1-Bedroom-House-In-Beautiful-Mount-Sterling.h124466713.Hotel-Information)

Mount Sterling

CA $122

CA $165 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Mount-Sterling-Hotels-Cozy-1-Bedroom-House-In-Beautiful-Mount-Sterling.h124466713.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Apartments

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Cottages

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-04-21&d1=2026-04-21&endDate=2026-04-24&d2=2026-04-24&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Springhill Suites by Marriott Lexington Fritz Farm](https://images.trvl-media.com/lodging/103000000/102370000/102366200/102366172/0a801b9d_y.jpg)

### Springhill Suites by Marriott Lexington Fritz Farm

10/10 Excellent

"We stay here a lot and have not had any complaints. Professional staff, great location, clean updated rooms and hot breakfast! "

[](https://expedia.ca/Lexington-Hotels-Springhill-Suites-By-Marriott-Lexington-South.h102366172.Hotel-Information)

![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/2fd2c43b_y.jpg)

### The Campbell House Lexington, Curio Collection by Hilton

10/10 Excellent

"always a charming experience at the campbell house,its my favourite place and I love Kentucky "

[](https://expedia.ca/Lexington-Hotels-The-Campbell-House-Lexington.h27029.Hotel-Information)

![The Manchester ](https://images.trvl-media.com/lodging/93000000/92440000/92430600/92430541/f02815a4_y.jpg)

### The Manchester 

10/10 Excellent

"Great place to stay, eat and drink."

[](https://expedia.ca/Lexington-Hotels-The-Manchester.h92430541.Hotel-Information)

![21c Museum Hotel Lexington](https://images.trvl-media.com/lodging/13000000/12250000/12243800/12243775/7f6a345c_y.jpg)

### 21c Museum Hotel Lexington

10/10 Excellent

"Great stay. Loved the hotel and restaurant "

[](https://expedia.ca/Lexington-Hotels-21c-Museum-Hotel-Lexington.h12243775.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Lexington South / Hamburg](https://images.trvl-media.com/lodging/1000000/290000/283200/283165/8b90557f_y.jpg)

### La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

10/10 Excellent

"Easy access from I 75\. Comfy beds. Will stay again."

[](https://expedia.ca/Lexington-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Lexington-South-Hamburg.h283165.Hotel-Information)

![DoubleTree Suites by Hilton Hotel Lexington](https://images.trvl-media.com/lodging/1000000/10000/9900/9900/f18d8c34_y.jpg)

### DoubleTree Suites by Hilton Hotel Lexington

10/10 Excellent

"Clean room love this place"

[](https://expedia.ca/Lexington-Hotels-DoubleTree-Suites-By-Hilton-Hotel-Lexington.h9900.Hotel-Information)

![Hilton Lexington/Downtown](https://images.trvl-media.com/lodging/1000000/10000/2200/2101/b9ab6063_y.jpg)

### Hilton Lexington/Downtown

10/10 Excellent

"Nice quiet room. Staff were very helpful."

[](https://expedia.ca/Lexington-Hotels-Hilton-LexingtonDowntown.h2101.Hotel-Information)

![Hyatt Regency Lexington](https://images.trvl-media.com/lodging/1000000/10000/3500/3461/c0c49295_y.jpg)

### Hyatt Regency Lexington

10/10 Excellent

"Clean room. Delicious breakfast and very convenient for UK Basketball "

[](https://expedia.ca/Lexington-Hotels-Hyatt-Regency-Lexington.h3461.Hotel-Information)

![Elwood Hotel & Suites](https://images.trvl-media.com/lodging/3000000/2220000/2219800/2219782/f131bcc5_y.jpg)

### Elwood Hotel & Suites

10/10 Excellent

"Friendly staff, clean room, easy check in and out. "

[](https://expedia.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information)

## Find out more about Winchester

## Winchester Vacation Homes information

| Number of reviews | 207                |
| ----------------- | ------------------ |
| Accommodation     | 437 Vacation Homes |
| Lowest Price      | CA $242            |
| Highest Price     | CA $683            |

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