Title: Winchester Cottages from CA $238 | Expedia.ca

  

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# Search Winchester Cottage Rentals from CA $238

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select 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)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a8cc2147.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/108000000/107620000/107613900/107613898/5f5b32cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vue - Mountain top hot tub overlooking the Shenandoah River

Front Royal

9.8/10

Exceptional

(8)

"Love the view and beautiful appointed decor throughout the home…"

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

Lynn M.

CA $234

CA $545 total

includes taxes & fees

Nov 6 - Nov 7

[](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)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/59a5c7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

Front Royal

10/10

Exceptional

(1)

CA $254

CA $638 total

includes taxes & fees

Nov 18 - Nov 19

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

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/5808d310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/2626f01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/5c5c28f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/117000000/116110000/116109100/116109067/1ee12ba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hike, Sip & Explore: Charming Waterford Cottage!

Waterford

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

![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)

![Dining](https://images.trvl-media.com/lodging/90000000/89680000/89671500/89671491/f9a86612.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)

### Cozy Retreat - Hot tub + Mountain Views + Pets

Fort Valley

9.8/10

Exceptional

(51)

"This house was super charming and perfect for our weekend getaway!"

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

Beth S.

CA $117

CA $363 total

includes taxes & fees

Oct 27 - Oct 28

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

![Interior](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/21ddc248.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)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72540000/72536300/72536217/3209a5cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry

10/10

Exceptional

(19)

"Pretty cabin with a wonderful view, especially from the hot tub. We will return!"

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

Holly C.

CA $140

CA $528 total

includes taxes & fees

Oct 30 - Oct 31

[](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/76000000/75200000/75194000/75193967/5fb45cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/76000000/75200000/75194000/75193967/53a68b39.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)

![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)

### Lake View Retreat - Cottage Near a Peaceful Lake!

Harpers Ferry

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 $140

CA $504 total

includes taxes & fees

Nov 4 - Nov 5

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

![Interior](https://images.trvl-media.com/lodging/104000000/103990000/103986500/103986494/b6a3dcb0.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)

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

### Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Berkeley Springs

10/10

Exceptional

(15)

"This is a very comfortable, quiet, and clean home, easily accessible by GPS. Great for our family of 6 with plenty of room and the home is stocked with essentials and conveniences (books, games, extra air mattress, crib, booster seat, etc.) Would definitely stay again for a get away to Berkeley Springs."

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

Margaret Z.

CA $208

CA $582 total

includes taxes & fees

Oct 26 - Oct 27

[](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)

![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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/86000000/85250000/85242000/85241973/346044b3.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)

### Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry

9.8/10

Exceptional

(29)

"Really enjoyed stay home was great "

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

zachary b.

CA $154

CA $531 total

includes taxes & fees

Nov 5 - Nov 6

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89150000/89145600/89145580/ad3ff238.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)

### Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry

9.8/10

Exceptional

(23)

"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 $140

CA $476 total

includes taxes & fees

Nov 5 - Nov 6

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89660000/89657200/89657197/f4a48de2.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)

### Wild Hare Cottage

Purcellville

10/10

Exceptional

(8)

"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 $196

CA $332 total

includes taxes & fees

Oct 29 - Oct 30

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106010000/106001100/106001094/d576b284.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)

### Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Harpers Ferry

9.8/10

Exceptional

(19)

"Very nice property with convenient location! Within walking distance of down town. "

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

Logan S.

CA $231

CA $425 total

includes taxes & fees

Nov 3 - Nov 4

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

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

![Point of interest](https://images.trvl-media.com/lodging/79000000/78120000/78111000/78111000/927d6a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carriage House at Carrot Top Cottage

Harpers Ferry

9.8/10

Exceptional

(42)

"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 $137

CA $238 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Harpers-Ferry-Hotels-The-Carriage-House-At-Carrot-Top-Cottage.h78111000.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/95000000/94960000/94956400/94956322/7e7ce3d1.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)

![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)

### 'thomson Farm' Classic Home < 10 Mi to Vineyards!

Leesburg

CA $1,680

CA $2,589 total

includes taxes & fees

Oct 26 - Oct 27

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

![Property grounds](https://images.trvl-media.com/lodging/111000000/110850000/110841300/110841279/19ec7694.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)

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

### The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hamilton

9.6/10

Exceptional

(7)

"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 $315

CA $549 total

includes taxes & fees

Oct 26 - Oct 27

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

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w508h683x258y0-7f4d529e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Waterfall House -- 2 bedroom hidden treasure

Berkeley Springs

9.6/10

Exceptional

(9)

"What a nice, history rich house to stay in. You can tell it has old bones but has been maintained and is full of character. Loved the relaxing setting with the river running around the house. Plenty to explore on the property down by the water and in the woods. Exactly what’s needed for a relaxing get away. Close to town as well for anything needed. Kirsten was a great host. "

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

Matt W.

CA $281

CA $442 total

includes taxes & fees

Oct 30 - Oct 31

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

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89630000/89626300/89626269/0ba870a3.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)

### Cottage by the Caverns \*FIRE PIT\* \*MOUNTAIN VIEWS\*

Luray

9.8/10

Exceptional

(78)

"This is a cute property with great proximity to Shenandoah National Park. The house had everything needed. The property owners provided excellent communication to make sure evertything was nice! Our time there was wonderful."

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

Jillene C.

CA $224

CA $455 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Luray-Hotels-Cottage-By-The-Caverns-FIRE-PIT-MOUNTAIN-VIEWS.h89626269.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/92000000/91040000/91035100/91035005/98988d32.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)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/92000000/91040000/91035100/91035005/05617209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Royal Heritage Home @ Historic Leesburg

Leesburg's Old and Historic District

9.8/10

Exceptional

(37)

"The host Michael was very attentive and helpful. The house had all we needed and walking distance to shops and food. Would highly recommend staying here! "

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

Dawn V.

CA $266

CA $623 total

includes taxes & fees

Nov 5 - Nov 6

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

![Interior](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/5819284e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/183f1019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/82963c99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113640000/113638100/113638012/2ddc1017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Creekside Cottage: Downtown | Pet-Friendly

Shepherdstown

10/10

Exceptional

(2)

"pet friendly, perfect spot in relation to downtown,,,,very quaint loved it!!!!"

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

BECKY H.

CA $308

CA $505 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Shepherdstown-Hotels-The-Creekside-Cottage-Downtown-Pet-Friendly.h113638012.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/ec6d4c2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/95c01c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/50231d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113890000/113882000/113881924/023a745c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Harpers Ferry

9.4/10

Exceptional

(6)

"We really enjoyed our stay, the four bedrooms gave us lots of space. The hot tub was great and we enjoyed the balcony, too. Very close to lots of fun wineries and Harper’s Ferry. Quiet location on a road with other houses. I’d recommend bringing extra towels and a few wine glasses if you’re drinking nice wine. Lots of thoughtful touches — games, fireplace, spacious kitchen. It was great!"

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

Renee P.

CA $344

CA $942 total

includes taxes & fees

Oct 30 - Oct 31

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

![Exterior](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e5d7776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/bc6898f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/e29f28d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/94000000/93520000/93510500/93510450/2b9acd11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

10/10

Exceptional

(49)

"What a peaceful place and wonderful views."

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

Debbie M.

CA $385

CA $551 total

includes taxes & fees

Oct 29 - Oct 30

[](https://www.expedia.ca/Middleburg-Hotels-18th-Century-Stone-Cottage-Minutes-From-Historic-Middleburg.h93510450.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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## Top Winchester Hotel Reviews

![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg)

### Comfort Inn & Suites Winchester

10/10 Excellent

"Clean rooms and comfortable beds and bedding. Plentiful bath towels. Convenient location "

[](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information)

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"New contemporary hotel; comfortable bed and nicely decorated room. Good location to restaurants and the highway. Nice staff and good breakfast (standard food items). Only complaint is that need a few more parking spaces. "

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

![Motel 6 Winchester, VA](//images.trvl-media.com/lodging/1000000/50000/43100/43087/f87cf676_y.jpg)

### Motel 6 Winchester, VA

10/10 Excellent

"Very clean, safe. "

[](https://expedia.ca/Winchester-Hotels-Motel-6-Winchester.h43087.Hotel-Information)

![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg)

### Travelodge by Wyndham Winchester

10/10 Excellent

"Clean room. Good breakfast"

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

![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg)

### Hampton Inn Winchester-University/Mall Area

10/10 Excellent

"Parking area felt very safe. Fruit available for breakfast. "

[](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information)

![Fairfield Inn & Suites by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792_y.jpg)

### Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"We really enjoyed our stay. Check in was efficient. The room was clean and the bed was comfortable. The ventilation in the bathroom was great, the steam from the shower cleared up fast!"

[](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information)

![TRU By Hilton Winchester](//images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg)

### TRU By Hilton Winchester

10/10 Excellent

"ok visit"

[](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information)

![Spark by Hilton Winchester](//images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89_y.jpg)

### Spark by Hilton Winchester

10/10 Excellent

"They never changed the towels or cleaned out room, breakfast only serves hard boiled eggs"

[](https://expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information)

![Candlewood Suites Winchester by IHG](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg)

### Candlewood Suites Winchester by IHG

10/10 Excellent

"Megan is delightful"

[](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information)

## Find out more about Winchester

## Winchester Cottages information

| Number of reviews | 414 |
| --- | --- |
| Accommodation | 192 Cottages |
| Lowest Price | CA $238 |
| Highest Price | CA $2,589 |

## Frequently asked questions

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

> We think that vacations should be simple, so if you're in search of cottages in Winchester at a competitive price, Expedia has got your back. Keep costs down and check in to a cheap option far away from the city rush, or splurge on an upmarket cottage to spoil your favorite people.

### How can I find cheap cottages in Winchester?

> The easiest way to locate cheap cottages in Winchester is with Expedia's useful filter tool. Narrow your search results by star rating, amenities and budget to snag awesome prices in just a few keystrokes.

### What is there to do in Winchester near my cottage?

> Winchester has enough activities and sights to keep you on the hop for weeks, starting with [Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Winchester.d553248621561864838.Vacation-Attraction). [The Kernstown Battlefield](https://www.expedia.ca/The-Kernstown-Battlefield-Winchester.d553248621561864837.Vacation-Attraction), [Museum of the Shenandoah Valley](https://www.expedia.ca/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) and [Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Winchester.d6164018.Vacation-Attraction) are other fantastic attractions. If you're in town a while, [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) and [Handley Regional Library](https://www.expedia.ca/Handley-Regional-Library-Old-Town-Winchester.d6164024.Vacation-Attraction) are nice final touches to your itinerary.

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-   [Pet-Friendly Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Spa Hotels in Winchester Historic District](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels)
-   [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)
-   [Flights from Gore](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore)
-   [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)
-   [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester)
-   [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester)
-   [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester)
-   [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester)
-   [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester)
-   [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester)
-   [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)