Title: Holiday Rentals Winchester from £98: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

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## Check prices for these dates

In two weeks

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=7876&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=7876&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=7876&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=7876&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester holiday rentals

![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/42a5ffb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/fce36096.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/8f41e298.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/109000000/108570000/108566500/108566456/8b2dee1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Perch - NEW / Downtown!

[](https://www.expedia.co.uk/Lexington-Hotels-The-Perch-NEW-Downtown.h108566456.Hotel-Information)

Winchester

10/10

Exceptional

(2 reviews)

"The place was amazing! Very clean and comfortable. Great Italian restaurant down the street. Delicious dounuts around the corner.We went down to go into Lexington for Bourbon and wine tours. Would have liked to have a folder/ binder with information on what is in the area ( we did explore downtown) and also for information about checking out.We had 4 adults and could have used more towels (had 1 towel for each person) But we did make due.All in all would give this place 5 stars! We will be...

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

Angela G.

[](https://www.expedia.co.uk/Lexington-Hotels-The-Perch-NEW-Downtown.h108566456.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)

![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/w508h683x259y0-958562e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103570000/103570000/103569999/w918h683x47y0-3062291a.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.co.uk/Lexington-Hotels-4-Bed-3-Bath-Clean.h103569999.Hotel-Information)

Winchester

10/10

Exceptional

(6 reviews)

"Easy check in, Clean and close to everything. "

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

Vicky R.

£216

includes taxes & fees

8 Feb - 9 Feb

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

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

![Interior](https://images.trvl-media.com/lodging/113000000/112560000/112559200/112559158/8159b951.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)

![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.co.uk/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.

£232

includes taxes & fees

7 Feb - 8 Feb

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

![](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w508h683x258y0-bca1477a.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)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103580000/103570100/103570075/w509h683x258y0-44f88b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Winchester

[](https://www.expedia.co.uk/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.

£216

includes taxes & fees

8 Feb - 9 Feb

[](https://www.expedia.co.uk/Lexington-Hotels-The-Winchester.h103570075.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)

![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)

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

![Property grounds](https://images.trvl-media.com/lodging/68000000/67300000/67290900/67290847/0fa7fe0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Stanton

9.8/10

Exceptional

(47 reviews)

"A great place to stay while exploring the area"

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

lisa s.

£129

includes taxes & fees

8 Feb - 9 Feb

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

![Property grounds](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843362/f1599a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843362/w453h683x286y0-d459859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843362/18bbcf07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96850000/96843400/96843362/ffb4f7ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Furnished Glamping Tent/King Bed/Access to the Red River - Elusive Elk - #1

[](https://www.expedia.co.uk/Stanton-Hotels-Furnished-TeepeeGlampingKayak-Ramp-Access-On-The-Red-River.h96843362.Hotel-Information)

Stanton

10/10

Exceptional

(24 reviews)

"Loved our stay. Most definitely coming back, had everything you needed for "

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

cristal l.

£102

includes taxes & fees

19 Feb - 20 Feb

[](https://www.expedia.co.uk/Stanton-Hotels-Furnished-TeepeeGlampingKayak-Ramp-Access-On-The-Red-River.h96843362.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76160000/76153100/76153096/c666ab8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76160000/76153100/76153096/7cdefa36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/77000000/76160000/76153100/76153096/2726ec8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76160000/76153100/76153096/c83ac51e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing, cozy cabin in the heart of the Red River Gorge!

[](https://www.expedia.co.uk/Stanton-Hotels-Relaxing.h76153096.Hotel-Information)

Stanton

10/10

Exceptional

(128 reviews)

"If you’re looking for a nice quiet get away this place is great! All the amenities of home are here and the cabin was very clean! We had a great time!"

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

Sherri M.

£190

includes taxes & fees

8 Feb - 9 Feb

[](https://www.expedia.co.uk/Stanton-Hotels-Relaxing.h76153096.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 | Terrace/patio](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/278782c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, 2 Bedrooms, Kitchen | In-room dining](https://images.trvl-media.com/lodging/16000000/15440000/15437800/15437778/c7bf72a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Natural Bridge State Resort Park

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

Slade

8.6/10

Excellent

(1,800 reviews)

"Friendly staff, convenient the have a restaurant and tavern on site. There is great hiking right out the back door. Appreciated a quiet stay."

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

Kimberly

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

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/1656a0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/c80904f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/82087122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/115000000/114450000/114449900/114449821/93d4b238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

[](https://www.expedia.co.uk/Frenchburg-Hotels-Peaceful-Frenchburg-Cabin-W-Private-Hot-Tub.h114449821.Hotel-Information)

Frenchburg

10/10

Exceptional

(2 reviews)

"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "

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

Anonymous traveller

£192

includes taxes & fees

19 Feb - 20 Feb

[](https://www.expedia.co.uk/Frenchburg-Hotels-Peaceful-Frenchburg-Cabin-W-Private-Hot-Tub.h114449821.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91350000/91349600/91349553/19c72b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91350000/91349600/91349553/d4aefe05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91350000/91349600/91349553/502df3fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/92000000/91350000/91349600/91349553/cae89bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded & Tranquil Cabin \~ Near Red River Gorge

[](https://www.expedia.co.uk/Irvine-Hotels-Cozy-Rustic-Cabin-In-The-Woods-Appalachian-Mountain-Region.h91349553.Hotel-Information)

Irvine

10/10

Exceptional

(58 reviews)

"Super inviting and felt like home. . ."

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

Janet B.

£195

includes taxes & fees

8 Feb - 9 Feb

[](https://www.expedia.co.uk/Irvine-Hotels-Cozy-Rustic-Cabin-In-The-Woods-Appalachian-Mountain-Region.h91349553.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/ad0d3e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/a67e8575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/c2b53613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108520000/108513900/108513805/d2416d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountaintop Cottage 

[](https://www.expedia.co.uk/Stanton-Hotels-Mountaintop-Cottage.h108513805.Hotel-Information)

Stanton

10/10

Exceptional

(27 reviews)

"I cannot say enough how CUTE this was we were so happy we found it. Loved the animals and will definitely stay again."

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

Jessica H.

£144

includes taxes & fees

9 Mar - 10 Mar

[](https://www.expedia.co.uk/Stanton-Hotels-Mountaintop-Cottage.h108513805.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)

![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)

![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)

### Mountain Memories Cabin

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

Stanton

10/10

Exceptional

(63 reviews)

"Great cabin!!"

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

Amanda S.

£152

includes taxes & fees

18 Feb - 19 Feb

[](https://www.expedia.co.uk/Stanton-Hotels-Mountain-Memories-Cabin.h100358030.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)

![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)

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

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

[](https://www.expedia.co.uk/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

£126

includes taxes & fees

8 Feb - 9 Feb

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113090000/113086400/113086392/9495225f.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.co.uk/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.

£158

includes taxes & fees

1 Mar - 2 Mar

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

![Property grounds](https://images.trvl-media.com/lodging/45000000/44780000/44775000/44774926/3f402f5d.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.co.uk/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.

£136

includes taxes & fees

1 Mar - 2 Mar

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

![Exterior detail](https://images.trvl-media.com/lodging/102000000/101040000/101036900/101036870/58d8fecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, 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.co.uk/Lexington-Hotels-1800s-Historical-Log-Cabin-Near-I-75-Interstate.h101036870.Hotel-Information)

Lexington

9.4/10

Exceptional

(59 reviews)

"Friendly host, warm welcoming home. Loved all the antiques and it was very comfortable!"

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

J K.

£178

includes taxes & fees

1 Mar - 2 Mar

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

![Smart TV](https://images.trvl-media.com/lodging/83000000/82740000/82731100/82731078/a11c3560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82740000/82731100/82731078/b4baf384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/83000000/82740000/82731100/82731078/6a864013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/83000000/82740000/82731100/82731078/621f8a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy upstairs 2 bed/1 bath Richmond apt near EKU

[](https://www.expedia.co.uk/Lexington-Hotels-Cozy-Upstairs-2-Bed1-Bath-Richmond-Apt-Near-EKU.h82731078.Hotel-Information)

Richmond

10/10

Exceptional

(33 reviews)

"Always a great stay. We’ve stayed here several times, and will continue to do so when we visit our daughter at EKU. "

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

Angela B.

£102

includes taxes & fees

13 Feb - 14 Feb

[](https://www.expedia.co.uk/Lexington-Hotels-Cozy-Upstairs-2-Bed1-Bath-Richmond-Apt-Near-EKU.h82731078.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/64000000/63860000/63852400/63852330/15d79283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/64000000/63860000/63852400/63852330/a9d854aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/64000000/63860000/63852400/63852330/7150f6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63860000/63852400/63852330/35bd1d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury on Main / South

[](https://www.expedia.co.uk/Lexington-Hotels-Luxury-On-Main-South.h63852330.Hotel-Information)

Richmond

10/10

Exceptional

(44 reviews)

"Great place for a quick weekend getaway."

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

Jennifer

£127

includes taxes & fees

7 Feb - 8 Feb

[](https://www.expedia.co.uk/Lexington-Hotels-Luxury-On-Main-South.h63852330.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74100000/74098700/74098628/07150be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/75000000/74100000/74098700/74098628/de289dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, memory-foam beds, desk, WiFi](https://images.trvl-media.com/lodging/75000000/74100000/74098700/74098628/23389601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74100000/74098700/74098628/bded8025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 2bd 2ba - Near I75, No Steps, Free Wifi

[](https://www.expedia.co.uk/Lexington-Hotels-Modern-Townhouse-45-Miles-From-I-75-And-Free-WiFi.h74098628.Hotel-Information)

Richmond

9.8/10

Exceptional

(85 reviews)

"Clean, close to campus . Would definitely stay again. "

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

Christina K.

£153

includes taxes & fees

8 Feb - 9 Feb

[](https://www.expedia.co.uk/Lexington-Hotels-Modern-Townhouse-45-Miles-From-I-75-And-Free-WiFi.h74098628.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)

![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/6372f5d0.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)

![Dining](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/e9dba827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.co.uk/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.

£170

includes taxes & fees

4 Mar - 5 Mar

[](https://www.expedia.co.uk/Lexington-Hotels-East-Suite-Bleubird-Studio-Suites-Art-Gallery-Yoga-Boutique-Stay.h38198837.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.co.uk/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21&regionId=7876&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Kentucky%2C+United+States+of+America&regionId=7876&latLong=37.990078%2C-84.179649&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Origin Lexington a Wyndham Hotel](https://images.trvl-media.com/lodging/34000000/33800000/33790700/33790682/7bb47690_y.jpg)

### Origin Lexington a Wyndham Hotel

10/10 Excellent

"Location, room and cleaniliness."

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

![Country Inn & Suites by Radisson, Georgetown, KY](https://images.trvl-media.com/lodging/1000000/540000/532100/532007/2dacd96b_y.jpg)

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

10/10 Excellent

"The only issue was the TV didnt have many options."

[](https://expedia.co.uk/Lexington-Hotels-Country-Inn-Suites-By-Radisson.h532007.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

"Very cool hotel, good amenities, clean, spacious good price really enjoyed it"

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

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

### Elwood Hotel & Suites

10/10 Excellent

"Very clean and spacious rooms and the beds were very comfortable! Would definitely recommend. "

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

![Holiday Inn Lexington - Hamburg by IHG](https://images.trvl-media.com/lodging/23000000/22760000/22757700/22757695/776ae294_y.jpg)

### Holiday Inn Lexington - Hamburg by IHG

10/10 Excellent

"Very nice one bedroom suite. Very clean, spacious and comfortable. Nice restaurant and bar, and easy walk to other restaurants and stores nearby. Will definitely stay again."

[](https://expedia.co.uk/Lexington-Hotels-Holiday-Inn-Lexington-Hamburg.h22757695.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

"Friendly staff, clean room, comfy bed"

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

![Spark by Hilton Lexington Hamburg](https://images.trvl-media.com/lodging/1000000/10000/6700/6639/4dbc3493_y.jpg)

### Spark by Hilton Lexington Hamburg

10/10 Excellent

"Friendly front staff and other people I met"

[](https://expedia.co.uk/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.Hotel-Information)

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

### The Manchester 

10/10 Excellent

"Clean rooms, friendly staff, and good restaurants. I especially like the music selections played through the hotel."

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

![Everhome Suites Lexington - Horse Park](https://images.trvl-media.com/lodging/102000000/101180000/101171900/101171857/89ad308c_y.jpg)

### Everhome Suites Lexington - Horse Park

10/10 Excellent

"The room was amazing with wonderful amenities! The staff was all wonderful and I will suggest this hotel all my friends! "

[](https://expedia.co.uk/Lexington-Hotels-Everhome-Suites-Lexington-North.h101171857.Hotel-Information)

## Find out more about Winchester

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

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winchester holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winchester holiday rentals we have selected for you start as low as £98 per night. Entering your travel dates in the search wizard you might find even better deals!

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

At Expedia, we put the best Winchester holiday 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 holiday.

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.co.uk
- All accommodation types in Winchester

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- [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations)
- [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations)
- [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations)
- [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals)
- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
- [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals)
- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

- [Cabin Rentals in Winchester ](https://expedia.co.uk/Winchester-Cabins.d7876-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there holiday rentals in Winchester?

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

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

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