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

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## Check availability on Winchester Historic Hotels

Tonight

[Feb 12 - Feb 13](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-12&endDate=2026-02-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 13 - Feb 14](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-13&endDate=2026-02-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6056879&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=6056879&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester historic hotels

![Exterior](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/15ce3672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/6addc16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5243c98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mimslyn Inn Historic Hotels Of America

[](https://www.expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information)

Luray

9.0/10

Wonderful

(1,004 reviews)

"Perfect stay will stay again."

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

EDWARD

CA $112

CA $139 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/2fa7daaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9f32e90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/e91ea1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ❤️ Secluded 1940s Romantic Tiny House on the River

[](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information)

Shepherdstown

9.8/10

Exceptional

(71 reviews)

"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."

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

Kaleb C

CA $54

CA $142 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/64d9b733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor spa tub](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/2bf49b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/2dc032bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

[](https://www.expedia.ca/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information)

Rileyville

10/10

Exceptional

(345 reviews)

"Everything was perfect for our stay. "

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

Debbie O.

CA $201

CA $363 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information)

![Meeting facility](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/3313eea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/be340f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/ab0dab8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846200/6846102/8abafad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Airlie Hotel

[](https://www.expedia.ca/Warrenton-Hotels-Airlie-Hotel.h6846102.Hotel-Information)

Warrenton

8.6/10

Excellent

(340 reviews)

"The HVAC system was right outside our room and was humming all night. Everything was comfortable but our sleep was extremely disrupted."

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

Adam

CA $202

CA $251 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Warrenton-Hotels-Airlie-Hotel.h6846102.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/edab5469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/0c19b755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/f7fc0dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/b116227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub 

[](https://www.expedia.ca/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information)

Rileyville

10/10

Exceptional

(355 reviews)

"Great place!"

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

Donald C.

CA $213

CA $375 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/3b7c41d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/310143cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/ccabcced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/47a00baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

[](https://www.expedia.ca/Rileyville-Hotels-The-Chalet-Shenandoah-Valley-Getaway-W-Hot-Tub-Near-Luray.h21478041.Hotel-Information)

Rileyville

9.8/10

Exceptional

(313 reviews)

"Love our stay. Beautiful place. Scenic views were the best. "

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

Joyce F.

CA $214

CA $381 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Rileyville-Hotels-The-Chalet-Shenandoah-Valley-Getaway-W-Hot-Tub-Near-Luray.h21478041.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/3cd13b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, stereo, offices](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/540472e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/7847da47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/431a8bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

[](https://www.expedia.ca/Viewtown-Hotels-Surrounded-By-Majestic-Trees-Hilltop-Is-Located-In-The-Piedmont-Of-Virginia.h19978224.Hotel-Information)

Amissville

9.8/10

Exceptional

(89 reviews)

"Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is."

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

Lisa S.

CA $278

CA $577 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Viewtown-Hotels-Surrounded-By-Majestic-Trees-Hilltop-Is-Located-In-The-Piedmont-Of-Virginia.h19978224.Hotel-Information)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/64000000/63750000/63747000/63746954/4b69b6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/64000000/63750000/63747000/63746954/f2f17127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/64000000/63750000/63747000/63746954/20260487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63750000/63747000/63746954/bf0905a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Old Rag | Hot Tub | Mountain Farmhouse

[](https://www.expedia.ca/Sperryville-Hotels-Old-Rag-Trailhead.h63746954.Hotel-Information)

Sperryville

10/10

Exceptional

(21 reviews)

"Great house! Perfect for a hike at Old Ray. Nice owners too!"

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

Mary Margaret R.

CA $352

CA $814 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Sperryville-Hotels-Old-Rag-Trailhead.h63746954.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a816723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/99c8f223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a4b6c89d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/3166dbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment

[](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.Hotel-Information)

The Plains

10/10

Exceptional

(6 reviews)

"The hosts are amazing! So accommodating and welcoming. The place is something special. "

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

AMY B.

CA $335

CA $550 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33493100/33493002/8eb2c99c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33493100/33493002/c6173421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33493100/33493002/3ccb2362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33500000/33493100/33493002/f364835e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jive!

[](https://www.expedia.ca/Luray-Hotels-The-Jive.h33493002.Hotel-Information)

Luray

9.8/10

Exceptional

(98 reviews)

"Great location and great time."

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

Cindy P.

CA $369

CA $665 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Luray-Hotels-The-Jive.h33493002.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=2026-02-26&endDate=2026-02-27&regionId=6056879&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

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## 

The Annual Vacation Sale 

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

[Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_6056879)

## Top Winchester Hotel Reviews

![Holiday Inn Express & Suites Leesburg - Historic District by IHG](https://images.trvl-media.com/lodging/1000000/600000/596500/596430/6cf9400d_y.jpg)

### Holiday Inn Express & Suites Leesburg - Historic District by IHG

10/10 Excellent

"All good"

[](https://expedia.ca/Leesburg-Hotels-Holiday-Inn-Express-And-Suites-Leesburg-Historic-District.h596430.Hotel-Information)

![Hilton Garden Inn Dulles North](https://images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg)

### Hilton Garden Inn Dulles North

10/10 Excellent

"Room with Jacuzzi tub in it was so nice. Everything spotless great stay! Recommended! "

[](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg)

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean and neat. Staff excellent 👍👍.First rate pool. "

[](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information)

![Hampton Inn Martinsburg](https://images.trvl-media.com/lodging/1000000/70000/63100/63064/835cd022_y.jpg)

### Hampton Inn Martinsburg

10/10 Excellent

"Staff are all amazing. Very helpfully and pleasant to deal with. Rooms were perfect. "

[](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Martinsburg.h63064.Hotel-Information)

![Holiday Inn Express Charles Town by IHG](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg)

### Holiday Inn Express Charles Town by IHG

10/10 Excellent

"Staff were very friendly and helpful. The room was clean, but the bathroom in 1054 needs"

[](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information)

![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg)

### Travelodge by Wyndham Winchester

10/10 Excellent

"Room was good for the price, staff was friendly and helpful "

[](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information)

![Mimslyn Inn Historic Hotels Of America](https://images.trvl-media.com/lodging/10000000/9770000/9760500/9760491/5175eb5d_y.jpg)

### Mimslyn Inn Historic Hotels Of America

10/10 Excellent

"Room was clean, food was great, staff was friendly. And the views were magnificent!"

[](https://expedia.ca/Luray-Hotels-Mimslyn-Inn-Historic-Hotels-Of-America.h9760491.Hotel-Information)

![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg)

### Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent

"The staff was wonderful! "

[](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information)

![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg)

### The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"Clean nice room Great location for restaurants "

[](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information)

## Frequently asked questions

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

### What's the best hotel in Winchester to be near historical sites?

### How many historically relevant hotels will I find in Winchester?

### What are the top historical sites and other places 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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- [Flights to Boyce ](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights)
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- [Appleland Sports Center ](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction)
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- [Visit Millwood ](https://www.expedia.ca/Millwood.dx3000460156)

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