Title: Book the Best HISTORIC Hotels in Winchester in 2026 | Expedia.ca

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![Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there ](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Nawa Aseen

![](https://images.trvl-media.com/place/7876/9403688e-dbbb-4255-9528-8bddb2ed4db3.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Winchester Historic Hotels

Tonight

[Feb 9 - Feb 10](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-09&endDate=2026-02-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 10 - Feb 11](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-10&endDate=2026-02-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=7876&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

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

## Our top choices for Winchester historic hotels

![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)

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

![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.ca/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.

CA $130

CA $246 total

includes taxes & fees

Mar 1 - Mar 2

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

![Exterior](https://images.trvl-media.com/lodging/30000000/29640000/29631000/29630955/ea1dc513.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/30000000/29640000/29631000/29630955/9f6bfe98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631000/29630955/a21684a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29631000/29630955/aa7d9389.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Downtown Two Bedroom Apartment in Downtown Lexington near Rupp Arena

[](https://www.expedia.ca/Lexington-Hotels-Downtown-Two-Bedroom-Apartment-In-Downtown-Lexington-Near-Rupp-Arena-And-Alltech.h29630955.Hotel-Information)

Downtown Lexington

9.8/10

Exceptional

(106 reviews)

"Close to Rupp Arena. Great place to stay."

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

Matthew C.

CA $146

CA $283 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Lexington-Hotels-Downtown-Two-Bedroom-Apartment-In-Downtown-Lexington-Near-Rupp-Arena-And-Alltech.h29630955.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/52b1d9d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/17cea644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/c163da2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99270000/99262400/99262314/8de63351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quiet Downtown Lexington Bougie Apartment

[](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information)

Downtown Lexington

9.6/10

Exceptional

(4 reviews)

"Great location in downtown Lexington! The place was clean and well appointed. We would definitely rent again! "

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

Bernadette R.

CA $164

CA $300 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Lexington-Hotels-175-LEX-Downtown-Condo-On-Main-St-W-Full-Kitchen.h99262314.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/37dc7dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/db9608c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/3f48eff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/98000000/97010000/97001100/97001020/w1324h900x25y0-a508f784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bourbon Condo Downtown Lexington

[](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.Hotel-Information)

Downtown Lexington

10/10

Exceptional

(12 reviews)

"Great stay and very clean!"

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

Nathan L.

CA $203

CA $387 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Lexington-Hotels-Bourbon-Condo-Downtown-Lexington.h97001020.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)

![Dining](https://images.trvl-media.com/lodging/39000000/38200000/38198900/38198837/e9dba827.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)

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

[](https://www.expedia.ca/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.

CA $171

CA $315 total

includes taxes & fees

Mar 1 - Mar 2

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

![Exterior](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/e0e7ce75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/552aa482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/ed8c69b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/35000000/34090000/34088500/34088471/29f4dcb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

[](https://www.expedia.ca/Lexington-Hotels-Lafferty-House-Walk-To-UK.h34088471.Hotel-Information)

Downtown Lexington

10/10

Exceptional

(53 reviews)

"Great Stay "

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

Anthony

CA $306

CA $559 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Lexington-Hotels-Lafferty-House-Walk-To-UK.h34088471.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/bbfb6def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/50928ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/41ce5864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/27000000/26960000/26955400/26955325/68ae97c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Kentucky Horse Country

[](https://www.expedia.ca/Paris-Hotels-Cabin-In-Kentucky-Horse-Country.h26955325.Hotel-Information)

Bourbon County

10/10

Exceptional

(79 reviews)

"Beautiful property and great host. Paris is a quaint town but plenty of activities to do. "

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

Brandon K.

CA $444

CA $663 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Paris-Hotels-Cabin-In-Kentucky-Horse-Country.h26955325.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/2e346aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/ed30953c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/48ee1025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33650000/33642600/33642557/190d3861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location

[](https://www.expedia.ca/Lexington-Hotels-Morrison-Cabin-Offers-The-Finest-Interiors.h33642557.Hotel-Information)

Downtown Lexington

10/10

Exceptional

(150 reviews)

"We enjoyed our stay. It was clean, well taken care of, and very convenient to our needs. I would definitely book this property again."

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

Chris F.

CA $363

CA $652 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Lexington-Hotels-Morrison-Cabin-Offers-The-Finest-Interiors.h33642557.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/20000000/20000000/19994900/19994818/3c02a6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/20000000/20000000/19994900/19994818/b927a4a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/20000000/20000000/19994900/19994818/87e2780c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/20000000/20000000/19994900/19994818/92d415fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private One Bedroom Apartment in Downtown Lexington near Rupp Arena

[](https://www.expedia.ca/Lexington-Hotels-Private-One-Bedroom-Apartment-In-Downtown-Lexington-Near-Rupp-Arena.h19994818.Hotel-Information)

Downtown Lexington

10/10

Exceptional

(159 reviews)

"Absolutely lovely! Cozy and quiet and a wonderful stay "

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

Elicia N.

CA $135

CA $229 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Lexington-Hotels-Private-One-Bedroom-Apartment-In-Downtown-Lexington-Near-Rupp-Arena.h19994818.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.ca/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&regionId=7876&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Winchester Hotel Reviews

![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

"This was the cleanest hotel I have stay at and that’s saying a lot considering how much ch I travel. No the breakfast isn’t eggs bacon ect. But you won’t be disappointed. Cereal bagels toast juice coffee. If that’s not for you fine but stop dinging them for breakfast. "

[](https://expedia.ca/Lexington-Hotels-Spark-By-Hilton-Lexington-Hamburg.h6639.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

"This place is super cute. A little outdated but my room was comfortable and clean and the bed is so cozy. Food and coffee are great. Staff is lovely. "

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

10/10 Excellent

"All was good "

[](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-LexingtonUK-Coldstream.h203587.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.ca/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.ca/Lexington-Hotels-Elwood-Hotel-Suites.h2219782.Hotel-Information)

![Embassy Suites by Hilton Lexington Green](https://images.trvl-media.com/lodging/1000000/10000/1600/1598/1dd182aa_y.jpg)

### Embassy Suites by Hilton Lexington Green

10/10 Excellent

"Excellent service! "

[](https://expedia.ca/Lexington-Hotels-Embassy-Suites-By-Hilton-Lexington-Green.h1598.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

"Very Clean Room, Friendly Staff, had some construction going on but no loud noises. Great hot breakfast, great location."

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

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

### Hyatt Regency Lexington

10/10 Excellent

"Overall, it's good. The room is clean. The breakfast is delicious, but you have to order it yourself, which is relatively expensive."

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

![Fairfield Inn & Suites by Marriott Lexington North](https://images.trvl-media.com/lodging/3000000/2810000/2803700/2803646/6ec64b2f_y.jpg)

### Fairfield Inn & Suites by Marriott Lexington North

10/10 Excellent

"Check in was quick and easy. Friendly staff. The room was clean and comfortable, perfect for our one night stay and quick visit. "

[](https://expedia.ca/Lexington-Hotels-Fairfield-Inn-Suites-By-Marriott-Lexington-North.h2803646.Hotel-Information)

## Frequently asked questions

### What should I expect on my historical trip to Winchester?

### How many historical hotels are located in Winchester?

### What are the most important historical places and other sights to visit in Winchester?

### What is a historic hotel like in Winchester?

### What is the difference between a historic hotel and a heritage hotel?

### Do historic hotels in Winchester have modern facilities?

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