Title: Winchester Vacation Rentals from $128: Search Short-Term Rentals | Expedia.com

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![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=7876&startDate=2026-07-03&endDate=2026-07-05&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 rentals

![](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w508h683x258y0-bca1477a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w508h683x258y0-9e510700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w527h683x257y0-f6968ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w908h683x59y0-c3ef6b09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Winchester

[](https://www.expedia.com/Lexington-Hotels-The-Winchester.h103570075.Hotel-Information)

Winchester

8.4/10

Very Good

(7 reviews)

"I rented this house for my bridesmaids. It was a great location and house. The owner was accommodating and replied quickly "

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

Karissa A.

$281 nightly

$309 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Lexington-Hotels-The-Winchester.h103570075.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w511h683x255y0-43dbacf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w508h683x259y0-958562e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w506h683x259y0-a92abcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w508h683x258y0-7896e0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4 Bed 3 bath clean , spacious all brick home , welcome families and work groups

[](https://www.expedia.com/Lexington-Hotels-4-Bed-3-Bath-Clean.h103569999.Hotel-Information)

Winchester

9.8/10

Exceptional

(7 reviews)

"Very homey place to stay! Nice neighborhood!"

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

Tim T.

$278 nightly

$306 total

Mar 27 - Mar 28

Total with taxes and fees

[](https://www.expedia.com/Lexington-Hotels-4-Bed-3-Bath-Clean.h103569999.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843358/cc4b9fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843358/11cadb79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843358/268159cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843358/b78cfa8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished Glamping Tent/2 Queen Beds/Red River Access- River Rainbow - #5

[](https://www.expedia.com/Stanton-Hotels-Furnished-TeepeeGlampingKayak-Ramp-Access-On-The-Red-River.h96843358.Hotel-Information)

Stanton

9.2/10

Wonderful

(12 reviews)

"Awesome stay! "

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

Cole R.

$119 nightly

$132 total

Mar 14 - Mar 15

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Furnished-TeepeeGlampingKayak-Ramp-Access-On-The-Red-River.h96843358.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67300000/67290900/67290847/0c1d218a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67300000/67290900/67290847/9c68d416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/68000000/67300000/67290900/67290847/f3d01e87_edited_7c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67300000/67290900/67290847/9b2ce646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Conveniently Located \~ WiFi \~ Central Heat & Air. 

[](https://www.expedia.com/Morehead-Hotels-The-Towner-Rrgnatural-Bridge.h67290847.Hotel-Information)

Stanton

9.8/10

Exceptional

(48 reviews)

"A great place to stay while exploring the area"

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

lisa s.

$143 nightly

$162 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Morehead-Hotels-The-Towner-Rrgnatural-Bridge.h67290847.Hotel-Information)

![Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/324d2660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/ebd7e3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/fa7fc3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, 2 Bedrooms, Kitchen | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/278782c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Natural Bridge State Resort Park

[](https://www.expedia.com/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information)

Slade

8.6/10

Excellent

(1,817 reviews)

"Clean room, staff was very friendly and helpful, excellent food. "

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

Amy

$116 nightly

$128 total

Apr 12 - Apr 13

Total with taxes and fees

[](https://www.expedia.com/Slade-Hotels-Natural-Bridge-State-Resort-Park.h15437778.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/109000000/108500000/108492100/108492045/d4447bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108492100/108492045/f06dca2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108500000/108492100/108492045/f1151ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108492100/108492045/3015e89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dappled Grey Cabin with hot tub at Red River Gorge

[](https://www.expedia.com/Stanton-Hotels-Dappled-Grey-Cabin-With-Hot-Tub-At-Red-River-Gorge.h108492045.Hotel-Information)

Stanton

10/10

Exceptional

(6 reviews)

"Great location, nice amentities (loved the hot tub), loved seeing the chickens and the dog that came to say hi"

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

Jessica

$209 nightly

$215 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Dappled-Grey-Cabin-With-Hot-Tub-At-Red-River-Gorge.h108492045.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100360000/100358100/100358030/917fea10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100360000/100358100/100358030/c4549f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100360000/100358100/100358030/32372526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100360000/100358100/100358030/w904h683x60y0-eb573d5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Memories Cabin

[](https://www.expedia.com/Stanton-Hotels-Mountain-Memories-Cabin.h100358030.Hotel-Information)

Stanton

10/10

Exceptional

(65 reviews)

"We enjoyed the homey feel and the quiet outdoors. The donkeys in a field nearby was the real treat. We loved everything about this place. "

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

Terri S.

$191 nightly

$211 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Mountain-Memories-Cabin.h100358030.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91360000/91351500/91351496/995b66fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91360000/91351500/91351496/8fe693ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91360000/91351500/91351496/a8fb4989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/92000000/91360000/91351500/91351496/7848badc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tranquil Getaway in the Woods \~ Sunset Ridge

[](https://www.expedia.com/Irvine-Hotels-ADA-Accessible-Cabin-In-The-Woods-Appalachian-Mountain-Region.h91351496.Hotel-Information)

Irvine

10/10

Exceptional

(93 reviews)

"Outstanding place to stay. Cozy and just what we hoped for. "

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

Benjamin Z.

$118 nightly

$130 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Irvine-Hotels-ADA-Accessible-Cabin-In-The-Woods-Appalachian-Mountain-Region.h91351496.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102550000/102549700/102549653/c60e979e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102550000/102549700/102549653/4778c827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102550000/102549700/102549653/ad017a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102550000/102549700/102549653/788a6b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Briar Patch Cabin RRG: Firepit, Sunset, WIFI

[](https://www.expedia.com/Stanton-Hotels-Briar-Patch-Cabin-RRG-Firepit.h102549653.Hotel-Information)

Stanton

10/10

Exceptional

(42 reviews)

"The cabin was very clean and absolutely beautiful! Check in was a breeze and host was very kind."

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

Stacy B.

$191 nightly

$211 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Briar-Patch-Cabin-RRG-Firepit.h102549653.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101040000/101036900/101036870/d0c2a8e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101040000/101036900/101036870/eabb5d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101040000/101036900/101036870/70689771.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101040000/101036900/101036870/4e55b506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1800’s Historical Log Cabin near I-75 Interstate 

[](https://www.expedia.com/Lexington-Hotels-1800s-Historical-Log-Cabin-Near-I-75-Interstate.h101036870.Hotel-Information)

Lexington

9.4/10

Exceptional

(59 reviews)

"Excellent stopover. "

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

Robert W.

$203 nightly

$236 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Lexington-Hotels-1800s-Historical-Log-Cabin-Near-I-75-Interstate.h101036870.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107640000/107632700/107632606/0e8ced23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107640000/107632700/107632606/a5160f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, video games](https://images.trvl-media.com/lodging/108000000/107640000/107632700/107632606/fbf93bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/108000000/107640000/107632700/107632606/1c6fffb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub! Tiny House Retreat in the Woods

[](https://www.expedia.com/Stanton-Hotels-Hot-Tub-Tiny-House-Retreat-In-The-Woods.h107632606.Hotel-Information)

Stanton

8.0/10

Very Good

(8 reviews)

"The cabin was just the right size for my wife and I. We enjoyed the lovely views from the porch and a good soak in the hot tub. We would recommend it to anyone wanting a quick quiet getaway."

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

Josh C.

$164 nightly

$181 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Hot-Tub-Tiny-House-Retreat-In-The-Woods.h107632606.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)

![TV](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/3076f388.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)

![Interior](https://images.trvl-media.com/lodging/84000000/83790000/83782100/83782041/584f264a.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.com/Lexington-Hotels-This-House-Is-A-2-Bedroom.h83782041.Hotel-Information)

Georgetown

8.6/10

Excellent

(33 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.

$175 nightly

$177 total

Mar 15 - Mar 16

Total with taxes and fees

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/a5d982e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/58f70ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/a160cec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/2be214c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Unique Stay in a 1907 Log Cabin on The Kentucky River

[](https://www.expedia.com/Lexington-Hotels-Unique-Stay-In-A-1907-Log-Cabin-On-The-Kentucky-River.h44774926.Hotel-Information)

Lexington

9.6/10

Exceptional

(108 reviews)

"Stayed for one night to ease a long drive to Florida. Would recommend and dog friendly."

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

Ashley G.

$155 nightly

$180 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Lexington-Hotels-Unique-Stay-In-A-1907-Log-Cabin-On-The-Kentucky-River.h44774926.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113090000/113086400/113086392/8d7796f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113090000/113086400/113086392/9495225f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113090000/113086400/113086392/4af517ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113090000/113086400/113086392/09200130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 240 Sq Ft Tiny Home w/ WIFI in Irvine

[](https://www.expedia.com/Irvine-Hotels-240-Sq-Ft-Tiny-Home-W-WIFI-In-Irvine.h113086392.Hotel-Information)

Irvine

10/10

Exceptional

(11 reviews)

"We love our vacations simple and this place made just that happen! Close enough to get to places to see yet far enough away for perfect privacy! We really enjoyed our stay! "

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

Samantha M.

$191 nightly

$211 total

Mar 14 - Mar 15

Total with taxes and fees

[](https://www.expedia.com/Irvine-Hotels-240-Sq-Ft-Tiny-Home-W-WIFI-In-Irvine.h113086392.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/108000000/107300000/107294600/107294592/f4c2c80e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107300000/107294600/107294592/8a0d635e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/108000000/107300000/107294600/107294592/70b243e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/108000000/107300000/107294600/107294592/54d85320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Minutes to Nada Tunnel + Natural Bridge SP / Views - Hot Tub - Firepit

[](https://www.expedia.com/Slade-Hotels-NEW-LISTING-4BR-Cabin-With-HotTub-WiFi-5-Min-To-Nada-Tunnel-RRG.h107294592.Hotel-Information)

Stanton

9.6/10

Exceptional

(18 reviews)

"Overall the cabin was very nice. There were some minor maintenance issues, such as the electric fireplace not working and the remotes for the tv needing batteries, but it was a great cabin. We enjoyed our stay. "

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

Anonymous traveler

$426 nightly

$470 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Slade-Hotels-NEW-LISTING-4BR-Cabin-With-HotTub-WiFi-5-Min-To-Nada-Tunnel-RRG.h107294592.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93700000/93691500/93691401/64a1f2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/94000000/93700000/93691500/93691401/9697c051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93700000/93691500/93691401/a5383fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93700000/93691500/93691401/7dd75d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### THIS IS THE ONE!-COUPLE’S CABIN-HOT TUB-MOBILE BOOKING DISCOUNT-CLEAN-GREAT VIEW

[](https://www.expedia.com/Stanton-Hotels-The-DEN-Shipping-Container-Cabin-HotTub-High-Speed-WiFi-Great-View-BOOK-IT.h93691401.Hotel-Information)

Stanton

10/10

Exceptional

(120 reviews)

"Great place"

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

James M.

$209 nightly

$230 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-The-DEN-Shipping-Container-Cabin-HotTub-High-Speed-WiFi-Great-View-BOOK-IT.h93691401.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115120000/115111400/115111392/w1335h890x0y2-28c9d329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115120000/115111400/115111392/w1331h886x1y2-a3636a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115120000/115111400/115111392/9b937287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/116000000/115120000/115111400/115111392/w1186h886x0y0-7fe8c875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Hilltop Couples Cabin with Hot Tub & Red River Gorge Views

[](https://www.expedia.com/Stanton-Hotels-Luxury-Hilltop-Couples-Cabin-With-Hot-Tub-Red-River-Gorge-Views.h115111392.Hotel-Information)

Stanton

9.6/10

Exceptional

(17 reviews)

"We enjoyed our short trip to RRG. Cabin was comfortable and clean with easy access to our favorite spots."

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

Lauren R.

$248 nightly

$271 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-Luxury-Hilltop-Couples-Cabin-With-Hot-Tub-Red-River-Gorge-Views.h115111392.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110720000/110716800/110716796/f4e0b223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110720000/110716800/110716796/12f284e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110720000/110716800/110716796/e939246c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110720000/110716800/110716796/754b508b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Sky Cabin Red River Gorge - Hot Tub Wi-Fi

[](https://www.expedia.com/Frenchburg-Hotels-Blue-Sky-Cabin-Red-River-Gorge-Hot-Tub-Wi-Fi.h110716796.Hotel-Information)

Frenchburg

9.8/10

Exceptional

(19 reviews)

"Everything was great. It was a nice place to relax for a weekend. The kitchen is fully equipped so bring some groceries and make your own meals."

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

Randy S.

$263 nightly

$289 total

Apr 13 - Apr 14

Total with taxes and fees

[](https://www.expedia.com/Frenchburg-Hotels-Blue-Sky-Cabin-Red-River-Gorge-Hot-Tub-Wi-Fi.h110716796.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/2078de17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/1bae486e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/c989c8e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/6372f5d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

[](https://www.expedia.com/Lexington-Hotels-East-Suite-Bleubird-Studio-Suites-Art-Gallery-Yoga-Boutique-Stay.h38198837.Hotel-Information)

Georgetown

10/10

Exceptional

(60 reviews)

"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "

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

l v.

$209 nightly

$230 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Lexington-Hotels-East-Suite-Bleubird-Studio-Suites-Art-Gallery-Yoga-Boutique-Stay.h38198837.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/64000000/63870000/63869500/63869479/7b29426b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63870000/63869500/63869479/1d1654a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/64000000/63870000/63869500/63869479/0848b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/64000000/63870000/63869500/63869479/71367972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BEST CABIN EVER!-IN THE WOODS-SUPER CLEAN-HOT TUB-PAVED ROAD-NATURAL BRIDGE PARK

[](https://www.expedia.com/Stanton-Hotels-The-WOODS-Shipping-Container-Cabin-High-Speed-WiFi-Hot-Tub-Covered-Deck-RELAX.h63869479.Hotel-Information)

Stanton

10/10

Exceptional

(311 reviews)

"Great place will be returning "

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

mel k.

$243 nightly

$267 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Stanton-Hotels-The-WOODS-Shipping-Container-Cabin-High-Speed-WiFi-Hot-Tub-Covered-Deck-RELAX.h63869479.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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28&regionId=7876&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=APARTMENT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-06-11&d1=2026-06-11&endDate=2026-06-14&d2=2026-06-14&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Home2 Suites by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/58000000/57490000/57487400/57487334/f62e7bf5_y.jpg)

### Home2 Suites by Hilton Lexington Hamburg

10/10 Excellent

"Was great"

[](https://expedia.com/Panacea-Hotels-Home2-Suites-By-Hilton-Lexington-Hamburg.h57487334.Hotel-Information)

![Origin Lexington a Wyndham Hotel](https://images.trvl-media.com/lodging/34000000/33800000/33790700/33790682/a0877840_y.jpg)

### Origin Lexington a Wyndham Hotel

8/10 Good

"Good"

[](https://expedia.com/Lexington-Hotels-Origin-Hotel-Lexington.h33790682.Hotel-Information)

![Holiday Inn Express Lexington Horse Park Area by IHG](https://images.trvl-media.com/lodging/1000000/130000/123900/123895/b7d6b7de_y.jpg)

### Holiday Inn Express Lexington Horse Park Area by IHG

4/10 Poor

"The person above us making loud noise all night long l! Could not sleep "

[](https://expedia.com/Lexington-Hotels-Holiday-Inn-Express-Lexington-Horse-Park-Area-By-IHG.h123895.Hotel-Information)

![The Campbell House Lexington, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/30000/27100/27029/68f1f7a4_y.jpg)

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

10/10 Excellent

"Beautiful hotel in a great location. Loved our stay here the room was really spacious and the decor was beautiful."

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

![Motel 6 Lexington, KY - Airport](https://images.trvl-media.com/lodging/1000000/20000/18500/18423/c6ac75fa_y.jpg)

### Motel 6 Lexington, KY - Airport

10/10 Excellent

"Best"

[](https://expedia.com/Lexington-Hotels-Motel-6-Lexington.h18423.Hotel-Information)

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

### Elwood Hotel & Suites

8/10 Good

"Bathroom was very small. Beds were nice"

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

![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/db3edf18_y.jpg)

### Country Inn & Suites by Radisson, Georgetown, KY

10/10 Excellent

"The room was clean and spacious, and the staff was very accommodating."

[](https://expedia.com/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.Hotel-Information)

![Embassy Suites by Hilton Lexington/UK Coldstream](https://images.trvl-media.com/lodging/1000000/210000/203600/203587/32ffb492_y.jpg)

### Embassy Suites by Hilton Lexington/UK Coldstream

6/10 Okay

"Loved the new hotel room. Super clean. Was disappointed, we checked in at 6 and were given drink vouchers and the lady at the bar said it ended at 6:30 and she wouldn’t honor the voucher. The hotel was under construction but was never mentioned when booking. No pool. We were on a family vacation so that was disappointing. Great breakfast in the morning with lots of options!"

[](https://expedia.com/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.Hotel-Information)

![Marriott Lexington Griffin Gate Golf Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/15900/15892/79f835ef_y.jpg)

### Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent

"The hotel was very clean and relaxing. "

[](https://expedia.com/Lexington-Hotels-Lexington-Griffin-Gate-Marriott-Golf-Resort-Spa.h15892.Hotel-Information)

## Find out more about Winchester

**Everything you need to know about Winchester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Winchester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Winchester rentals**

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
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- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d7876-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.com/Winchester-Cabins.d7876-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d7876-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.com/Winchester-Condos.d7876-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d7876-aaCottages.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.com/Winchester-Agritourism.d7876-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.com/Winchester-Motels.d7876-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Winchester ](https://expedia.com/Winchester-RV-Parks.d7876-aaRVParks.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.com/Winchester-Lodges.d7876-aaLodges.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d7876-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.com/Winchester-Guest-Houses.d7876-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.com/Winchester-Chalets.d7876-aaChalets.Travel-Guide-Accommodation)
- [Resorts in Winchester ](https://expedia.com/Winchester-Resorts.d7876-aaResorts.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Winchester?

### What are some of the best vacation home rentals that Winchester has to offer?

### How many vacation rentals are there in Winchester?

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- [Georgetown Cheap Hotels](https://expedia.com/Georgetown-Hotels-Cheap-Hotels.0-0-d7990-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Georgetown](https://expedia.com/Georgetown-Hotels.d7990.Travel-Guide-Hotels)
- [Frankfort Hotels with an Indoor Pool](https://expedia.com/Frankfort-Hotels-Hotels-With-Indoor-Pool.0-0-d7262-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Georgetown Pet-friendly Hotels](https://expedia.com/Georgetown-Hotels-Pet-Friendly-Hotel.0-0-d7990-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Richmond Cheap Hotels](https://expedia.com/Richmond-Hotels-Cheap-Hotels.0-0-d6148-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Best Hotels in Frankfort](https://expedia.com/Frankfort-Hotels.d7262.Travel-Guide-Hotels)
- [Frankfort Luxury Hotels](https://expedia.com/Frankfort-Hotels-Luxury-Hotel.0-0-d7262-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Best Hotels in Wilmore](https://expedia.com/Wilmore-Hotels.d10316.Travel-Guide-Hotels)
- [Best Hotels in Versailles](https://expedia.com/Versailles-Hotels.d7459.Travel-Guide-Hotels)
- [Best Hotels in Nicholasville](https://expedia.com/Nicholasville-Hotels.d181401.Travel-Guide-Hotels)
- [Georgetown Hotels with an Indoor Pool](https://expedia.com/Georgetown-Hotels-Hotels-With-Indoor-Pool.0-0-d7990-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels)
- [Frankfort Cheap Hotels](https://expedia.com/Frankfort-Hotels-Cheap-Hotels.0-0-d7262-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Versailles 3 Star Hotels](https://expedia.com/3Star-Versailles-Hotels.s30-0-d7459.Travel-Guide-Filter-Hotels)
- [Best Hotels in Midway](https://expedia.com/Midway-Hotels.d6353983.Travel-Guide-Hotels)

Flights

- [Flights to LEX](https://expedia.com/Cheap-Flights-To-Versailles.d7459.Travel-Guide-Flights)
- [Flights to LEX](https://expedia.com/Cheap-Flights-To-Georgetown.d7990.Travel-Guide-Flights)
- [Flights to LEX](https://expedia.com/Cheap-Flights-To-Richmond.d6148.Travel-Guide-Flights)
- [Flights to LEX](https://expedia.com/Cheap-Flights-To-Frankfort.d7262.Travel-Guide-Flights)

Cars

- [Car rentals in Richmond](https://expedia.com/Car-Rentals-In-Richmond.d6148.Car-Rental-Guide)
- [Car rentals in Wilmore](https://expedia.com/Car-Rentals-In-Wilmore.d10316.Car-Rental-Guide)
- [Car rentals in Versailles](https://expedia.com/Car-Rentals-In-Versailles.d7459.Car-Rental-Guide)
- [Car rentals in Nicholasville](https://expedia.com/Car-Rentals-In-Nicholasville.d181401.Car-Rental-Guide)
- [Car rentals in Georgetown](https://expedia.com/Car-Rentals-In-Georgetown.d7990.Car-Rental-Guide)
- [Car rentals in Frankfort](https://expedia.com/Car-Rentals-In-Frankfort.d7262.Car-Rental-Guide)

Activities

- [Things to do in Frankfort](https://expedia.com/Things-To-Do-In-Frankfort.d7262.Travel-Guide-Activities)
- [Things to do in Georgetown](https://expedia.com/Things-To-Do-In-Georgetown.d7990.Travel-Guide-Activities)
- [Things to do in Versailles](https://expedia.com/Things-To-Do-In-Versailles.d7459.Travel-Guide-Activities)
- [Things to do in Nicholasville](https://expedia.com/Things-To-Do-In-Nicholasville.d181401.Travel-Guide-Activities)

General

- [Visit Frankfort](https://expedia.com/Frankfort.dx7262)

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