Title: Winchester Cottages from CA $235 | Expedia.ca

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# Search Winchester Cottage Rentals from CA $235

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6056879&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)

## Our top choices for Winchester cottages

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/1087f0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/8d41db14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

9.8/10

Exceptional

(10)

"We rented this property to do an away game night with friends and it was great. The set up was perfect. The view is stunning. The central space both upstairs (kitchen and living room) and downstairs are very open, leaving a great ability to interact with each other. Everything we needed was there, the beds were super comfortable. Also, I'm always nervous renting on here out of fear that the host won't communicate enough. That was never an issue. Josefine made sure we had the instructions...

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

Anonymous traveller

CA $176

CA $468 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/9a2bb6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/4c56e3e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/b8a5d193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

10/10

Exceptional

(2)

"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"

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

Jay L.

CA $185

CA $537 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/6364c41d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/4d2e2016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/adce4c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/c4395816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Berryville

[](https://www.expedia.ca/Berryville-Hotels-1800s-Cozy-Kitchen-House-In-Berryville.h108361347.Hotel-Information)

CA $199

CA $254 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Berryville-Hotels-1800s-Cozy-Kitchen-House-In-Berryville.h108361347.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/215d28e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/1920a52c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/d2f7032a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/40e0ea36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Fort Valley

[](https://www.expedia.ca/Fort-Valley-Hotels-NEW-Mountain-Views-Cottage-Near-Shenandoah.h89671491.Hotel-Information)

9.8/10

Exceptional

(53)

"It was a beautiful getaway from all of the busy mess from our normal lives"

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

Tailor N.

CA $96

CA $326 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Fort-Valley-Hotels-NEW-Mountain-Views-Cottage-Near-Shenandoah.h89671491.Hotel-Information)

![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/3037b62c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/1732e5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (Multiple Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/1bc8e0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (Multiple Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94960000/94956400/94956322/06cf4e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Leesburg

[](https://www.expedia.ca/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information)

CA $1,497

CA $2,520 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Leesburg-Hotels-Thomson-Farm-Classic-Home-10-Mi-To-Vineyards.h94956322.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/50e7f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/5b26230e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/ca0816c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Purcellville

[](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information)

10/10

Exceptional

(10)

"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "

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

Jennifer K.

CA $174

CA $300 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Purcellville-Hotels-Wild-Hare-Cottage.h89657197.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/5b084607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/78b93c17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/6dea0731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/467055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Berkeley Springs

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Quiet-Cottage-On-Five-Acres-Of-Woods-Close-To-All-That-BerkeleySprings-Offers.h103986494.Hotel-Information)

9.4/10

Exceptional

(19)

"Can't wait to come back to this beautiful home with my family! Amazing experience! "

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

Brandon L.

CA $205

CA $569 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Quiet-Cottage-On-Five-Acres-Of-Woods-Close-To-All-That-BerkeleySprings-Offers.h103986494.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/4ee9e17b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/b741e712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/86ea8301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/3f2e7420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information)

9.8/10

Exceptional

(30)

"What a great weekend we had! This cottage had everything you could possibly want for a weekend getaway. "

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

Elaine H.

CA $138

CA $502 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Peaceful-Lakefront-Cottage-With-Blue-Mountain-Views.h85241973.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/5fb45cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/f3f54889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/44a70f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/7c522db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information)

9.6/10

Exceptional

(21)

"The house was clean, had plenty of rooms and a fantastic location. "

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

Bryan N.

CA $138

CA $496 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Lake-View-Retreat-Cottage-Near-A-Peaceful-Lake.h75193967.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/4f1c9bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/efeff641.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/0861e87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88380000/88378600/88378587/b4ecc8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information)

10/10

Exceptional

(23)

"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"

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

Matthew P.

CA $152

CA $619 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Art-Docko-Lakefront-Artists-Retreat-For-A-Relaxing-Getaway.h88378587.Hotel-Information)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/19e03d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/e6c503ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/7bd3216c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/464cb9da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Carriage-House-At-Carrot-Top-Cottage.h78111000.Hotel-Information)

9.8/10

Exceptional

(43)

"The place was super cute and clean. It was the perfect little getaway spot for my husband and I’s anniversary. "

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

Holly W.

CA $135

CA $235 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Carriage-House-At-Carrot-Top-Cottage.h78111000.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/8e487be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/332db170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/ba004d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/fdfb6965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Amazing-Dog-Friendly-Cottage-Walk-2-Harpers-Ferry.h106001094.Hotel-Information)

9.8/10

Exceptional

(20)

"Really nice property, and exactly as advertised. There were several local restaurants within easy walking distance (we loved both Bolivar Bread and Snallygaster's) and it was a fairly easy walk to the historic part of Harper's Ferry. We also enjoyed the fire pit in the back yard."

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

Greg B.

CA $228

CA $413 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Amazing-Dog-Friendly-Cottage-Walk-2-Harpers-Ferry.h106001094.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/5bda07b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/b5421e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/27187ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/398ab711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Luray

[](https://www.expedia.ca/Luray-Hotels-Cottage-By-The-Caverns-FIRE-PIT-MOUNTAIN-VIEWS.h89626269.Hotel-Information)

9.8/10

Exceptional

(81)

"Great place. Really enjoyed our mountain getaway!"

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

Evan C.

CA $221

CA $434 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Luray-Hotels-Cottage-By-The-Caverns-FIRE-PIT-MOUNTAIN-VIEWS.h89626269.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w508h683x258y0-868506a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w508h683x259y0-e1f8247a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w507h683x258y0-4666fb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w506h683x260y0-07df7371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Berkeley Springs

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Peaceful-Waterfall-House-2-Bedroom-Hidden-Treasure.h101446518.Hotel-Information)

9.6/10

Exceptional

(10)

"The setting is peaceful and beautiful. The property has a rich history. The house has a lot of quirky character and exploring it is a trip within itself. We have stayed in several places in WV but this one is currently our favorite."

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

Gregory S.

CA $277

CA $434 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Peaceful-Waterfall-House-2-Bedroom-Hidden-Treasure.h101446518.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/06517d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/e639e91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/088a3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/8c362a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information)

9.4/10

Exceptional

(6)

"We enjoyed our stay , close to everything we planned for the weekend. Place was very roomy, clean and the beds were very comfortable!!"

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

Cheryl O.

CA $177

CA $748 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Spacious-Mtn-Pet-Friendly-Home-Hottub-Firepit.h113881924.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/7706e12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/91c01c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/c897e3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information)

9.8/10

Exceptional

(20)

"Great view, very secluded"

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

Matt s.

CA $138

CA $520 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Harpers-Ferry-Hotels-Mountaintop-Cottage-With-100-Mile-Views-Of-The-Shenandoah-Valley.h72536217.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/fa7cba31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/9cad6316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/682637e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/068d8c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Hamilton

[](https://www.expedia.ca/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information)

9.6/10

Exceptional

(9)

"It was a great place to starve whole experience was perfect. "

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

Jaime B.

CA $310

CA $511 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Hamilton-Hotels-The-Cottage-At-Firefly-Cellars.h110841279.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/99ff3ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/31dbe26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/134150ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/13657af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Harpers Ferry

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information)

9.8/10

Exceptional

(24)

"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."

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

Claudia F.

CA $138

CA $471 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-Woodsy-Retreat-With-A-Hot-Tub-And-Seasonal-Views-Of-The-Valley.h89145580.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/d310e7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/6f7d1d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/b2f47280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/5d5a16bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Waterford

[](https://www.expedia.ca/Waterford-Hotels-Hike.h116109067.Hotel-Information)

CA $379

CA $668 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Waterford-Hotels-Hike.h116109067.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/c8a1f4ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/cc14e518.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/98988d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/4f401016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Leesburg's Old and Historic District

[](https://www.expedia.ca/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.Hotel-Information)

9.8/10

Exceptional

(37)

"The property was perfect for our stay. We had everything we needed and the beds were very comfy. We will definitely stay here again!"

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

Andrew N.

CA $296

CA $626 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Leesburg-Hotels-Historic-Charmer-Downtown-Leesburg.h91035005.Hotel-Information)

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

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## Find vacation rentals that suit your style

Cabins

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Apartments

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Private vacation homes

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=VILLA)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Virginia%2C+United+States+of+America&regionId=6056879&latLong=39.184082%2C-78.165703&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CHALET)

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## Top Winchester Hotel Reviews

![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

"Comfortable and clean room."

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

![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg)

### Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Room was large, very clean and very comfortable."

[](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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 clean, heater works great parking "

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

![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg)

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Front desk staff was sweet. Checking out was a breeze. Room was great. Great Oishi restaurant, basically in the parking lot ! Would definitely stay here again "

[](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information)

![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg)

### Quality Inn Winchester

10/10 Excellent

"Everything was great, including breakfast "

[](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information)

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

### Hampton Inn Martinsburg

10/10 Excellent

"Front desk was very considerate and friendly. Hotel was very clean. "

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

"Super friendly reception and perfectly clean room. "

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

![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg)

### Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Staff is fantastic and breakfast is always great. "

[](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information)

![Holiday Inn Express Hotel & Suites Winchester by IHG](https://images.trvl-media.com/lodging/2000000/1100000/1090600/1090593/38caae92_y.jpg)

### Holiday Inn Express Hotel & Suites Winchester by IHG

10/10 Excellent

"Clean room, easy and quick check in."

[](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Hotel-Suites-Winchester.h1090593.Hotel-Information)

## Find out more about Winchester

## Winchester Cottages information

| Number of reviews | 413          |
| ----------------- | ------------ |
| Accommodation     | 191 Cottages |
| Lowest Price      | CA $235      |
| Highest Price     | CA $2,520    |

## Frequently asked questions

### Why book your cottage in Winchester with Expedia?

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- [Spa Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Old Town Winchester Hotels ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)
- [Hotels near Patsy Cline Historic House ](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels)
- [Lodges in Riverton ](https://www.expedia.ca/Riverton-Lodges.d553248635975849884-aaLodges.Travel-Guide-Accommodation)
- [Hotels near Rock Harbor Golf Course ](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels)
- [Cottages in Shawnee Land ](https://www.expedia.ca/Shawnee-Land-Cottages.d553248635975849755-aaCottages.Travel-Guide-Accommodation)
- [Hotels near Shenandoah University ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)
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- [B&B in Stephens City ](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Stephens City Hotels ](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels)
- [Hotels near Valerie Hill Winery ](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in White Post ](https://www.expedia.ca/White-Post-Hotels-Honeymoon-Hotels.0-0-d184119-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
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- [Hotels with Bar in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
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- [Hotels near Winchester Medical Center ](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels)

- [Flights to Boyce ](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights)
- [Flights to Millwood ](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights)
- [Flights from Winchester Regional ](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport)
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- [Flights from Clear Brook ](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook)
- [Flights from Blacksburg (BCB) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester)
- [Flights from Hartford (BDL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester)
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- [Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester)
- [Flights from Melbourne (MEL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester)
- [Flights from Sarasota (SRQ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester)
- [Flights from Syracuse (SYR) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester)
- [Flights from Calgary (YYC) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester)
- [Flights from Toronto (YYZ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester)

- [Appleland Sports Center ](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction)
- [Jim Barnett Park ](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction)
- [Visit Millwood ](https://www.expedia.ca/Millwood.dx3000460156)

- [Book Cottages in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation)