Title: Winchester Vacation Rentals from CA $147: Short-Term Rentals for 2025 | Expedia.ca

  

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# Winchester Vacation Rentals

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## Check prices for these dates

Tonight

[Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Winchester

## Our top choices for Winchester vacation rentals

![Pool](https://images.trvl-media.com/lodging/38000000/37280000/37274400/37274339/c64d6311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/38000000/37280000/37274400/37274339/5de6cbf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/38000000/37280000/37274400/37274339/dd321b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37280000/37274400/37274339/9b9e4779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Rileyville

10/10

Exceptional

(98)

"Clean and nice place to stay to visit Shenandoah "

CA $235

CA $566 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Rileyville-Hotels-Lone-Bear-Cabin-Lv2-EV.h37274339.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/9545f24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/2d866371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/fbadc1f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27132300/27132250/41d8d16c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs

9.8/10

Exceptional

(283)

"Very nice stay. We used the fire pit and hot tub and enjoyed both. Excellent location close to cacapon, we ended up hiking and doing the clay shooting. The cabin itself was very nice, cozy, and clean. "

CA $125

CA $420 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Private-Getaway-W-Hot-Tub.h27132250.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/22255107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Quadruple Room, Ensuite | Interior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/f229dd73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/5a919945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23010000/23004100/23004100/e82f2a35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Road Haven 1830

Mount Jackson

9.6/10

Exceptional

(36)

"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"

CA $179

CA $201 total

includes taxes & fees

Sep 29 - Sep 30

[](https://www.expedia.ca/Luray-Hotels-Family-Farmhouse-Inn.h23004100.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/9fcb6e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/cfaa6bcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/921193d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/6120de47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs

10/10

Exceptional

(46)

"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "

CA $245

CA $304 total

includes taxes & fees

Oct 8 - Oct 9

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information)

![Cabin, 1 Queen Bed, Mountain View](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/63dbb872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/4b8eadd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, 1 Queen Bed, Non Smoking, Mountain View](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/08eb3fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Mobile Home, 1 Queen Bed, Non Smoking, Mountain View](https://images.trvl-media.com/lodging/113000000/112100000/112098800/112098770/64262b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Canal Cabins

Paw Paw

9.6/10

Exceptional

(9)

"Perfect for an over night Clean quiet simple. Ac needs repair"

CA $172

CA $195 total

includes taxes & fees

Sep 27 - Sep 28

[](https://www.expedia.ca/Paw-Paw-Hotels-Canal-Cabins.h112098770.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/f6c9e6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/bb644d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/4867d85d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/106000000/105320000/105319100/105319025/b50d6997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private, light filled retreat space... with your own pickleball court!

Berkeley Springs

10/10

Exceptional

(47)

"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Private.h105319025.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/3d2436ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/dea97a57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/4e07b9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100820000/100818300/100818202/eb4d742e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Berkeley Springs

9.6/10

Exceptional

(11)

"Hot tub was nice relaxing cozy cabin"

CA $102

CA $268 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Rustic-Tabor-Woods-Cabin-Near-Cacapon-State-Park-WPatio.h100818202.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/48307a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/ba066be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/7ed36a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/159749b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Luray

9.6/10

Exceptional

(62)

"We had a great stay! The place was very clean, the back deck was such a great added bonus.. had a good selection of movies and games. 4 wheel drive is advisable. Very comfy!!"

CA $196

CA $444 total

includes taxes & fees

Oct 2 - Oct 3

[](https://www.expedia.ca/Luray-Hotels-Dog-Friendly-Shenandoah-Views-Wifi.h83542571.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/e001c092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/ef37595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/1bc4382f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/ee30ee65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville

9.8/10

Exceptional

(297)

"Well kept cabin in a secluded part of Shenandoah. Would book again!"

[](https://www.expedia.ca/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/2cb5e40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/b8faf3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/884cb38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/fb065307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Star view cabin-Riverfront

Rileyville

9.8/10

Exceptional

(331)

"Great location, great views, "

[](https://www.expedia.ca/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/0f1edc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/da43d08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/cf55968e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/96000000/95130000/95120300/95120287/ed85aff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Luray

10/10

Exceptional

(11)

"It was an amazing place, will recommend to friends and hopefully will be back."

CA $204

CA $337 total

includes taxes & fees

Sep 30 - Oct 1

[](https://www.expedia.ca/Rileyville-Hotels-Cute-Riverside-Cabin-W-Hot-Tub.h95120287.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78090000/78083300/78083220/6f2df554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78090000/78083300/78083220/67183bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78090000/78083300/78083220/c2089a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78090000/78083300/78083220/1718f4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Endless Skies & Spectacular Views!!!

Rileyville

10/10

Exceptional

(76)

"Gorgeous property, very peaceful, highly recommended!"

[](https://www.expedia.ca/Rileyville-Hotels-Endless-Skies-Spectacular-Views.h78083220.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113620000/113616700/113616631/4e9f0dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113620000/113616700/113616631/1215dc6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113620000/113616700/113616631/ba4dc141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113620000/113616700/113616631/8fdeec5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

Fort Valley

10/10

Exceptional

(6)

"This was a perfect weekend get away! Super clean. The host provided all the necessities that you might need like shampoo, soap, tissues, etc. The host was very prompt with responding to questions. Would definitely recommend! "

CA $417

CA $604 total

includes taxes & fees

Sep 28 - Sep 29

[](https://www.expedia.ca/Fort-Valley-Hotels-Modern-Glass-Retreat-In-Fort-Valley-With-WiFi.h113616631.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/3fb00335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/43f68831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/ba83a961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89360000/89355000/89354942/b0328aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Oculus - Huge Cabin with a Hot Tub!

Harpers Ferry

9.6/10

Exceptional

(24)

"This was a great place for our vacation."

CA $138

CA $602 total

includes taxes & fees

Oct 2 - Oct 3

[](https://www.expedia.ca/Harpers-Ferry-Hotels-NEW-The-Oculus-Huge-Cabin-In-The-Woods-With-A-Hot-Tub.h89354942.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9c1d9621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/1a9ef301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/80506691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Shepherdstown

10/10

Exceptional

(61)

"We truly loved this location and definitely will be back!"

CA $56

CA $147 total

includes taxes & fees

Oct 5 - Oct 6

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/91000000/90710000/90703500/90703485/50a62d50.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/91000000/90710000/90703500/90703485/4dcf7476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90710000/90703500/90703485/e90040c0_edited_cd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90710000/90703500/90703485/6e568de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1959 TOPLEY Retreat offers Serenity/Tranquility + Pets - Fenced Area/ FREE WIFI

Luray

10/10

Exceptional

(8)

"This is a lovely home and super clean. My partner and I stayed here for a long weekend to go hiking around Shenandoah. Luray was also a nice little town."

CA $242

CA $394 total

includes taxes & fees

Oct 13 - Oct 14

[](https://www.expedia.ca/Luray-Hotels-1959-TOPLEY-Retreat-Offering-Total-Serenity-On-The-Ridge.h90703485.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/26940000/26932100/26932044/54935849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/27000000/26940000/26932100/26932044/57bb035e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26940000/26932100/26932044/2985b151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/27000000/26940000/26932100/26932044/ed7734c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

Berkeley Springs

9.8/10

Exceptional

(123)

"The property was awesome. Very secluded, very clean, fully stocked. Check in is a little late and check out a little early, but would definitely stay again. The property was incredible with only little things like the electric fireplaces or the bubbles on the hottub not working. Plenty of space for a whole family, and plenty to do if you bring dogs. "

[](https://www.expedia.ca/Martinsburg-Hotels-Private-Log-Cabin-Hot-Tub.h26932044.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/034f0b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/a44c1480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/2e125837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22780000/22775200/22775112/8f0ff4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

Rileyville

9.4/10

Exceptional

(144)

"We had a very nice stay. Magnificent view from deck, sunrise and sunset. Pool was great for the 100 degree days we had, very refreshing. To hot for the hot tub this time. Definitely need 4wd/awd vehicle. Had a good time Thanks"

[](https://www.expedia.ca/Rileyville-Hotels-Spectacular-Views.h22775112.Hotel-Information)

![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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101450000/101446600/101446518/w507h683x259y0-14d954d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

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

Berkeley Springs

9.6/10

Exceptional

(8)

"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. "

CA $278

CA $437 total

includes taxes & fees

Sep 28 - Sep 29

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

![Outdoor dining](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/2791d502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/0aaeb11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/ec01e8fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/68000000/67390000/67385500/67385431/8fe9e87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Linden

10/10

Exceptional

(93)

"Very nice relaxing getaway, quite how do you spell quiet and serene location. "

[](https://www.expedia.ca/Front-Royal-Hotels-Whiskey-Hill-Cabin-A-Mountain-Getaway-In-Virginia-Wine-Country.h67385431.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

![Hilton Garden Inn Winchester](//images.trvl-media.com/lodging/3000000/2170000/2169500/2169428/689131eb_y.jpg)

### Hilton Garden Inn Winchester

10/10 Excellent

"A great stop for our family of four on a long drive home."

[](https://expedia.ca/Winchester-Hotels-Hilton-Garden-Inn-Winchester.h2169428.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

"Everyone who works at this hotel is friendly, helpful, and good at their jobs. While the listing on Hotels.com says they offer a free Continental breakfast, I was delighted to find it included bacon, eggs, and sausage and an elderly server who was very friendly and was constantly in motion checking and replacing different foods that were running low. In short, everyone at this place is gracious, friendly, competent, and CARES!!!"

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

![TownePlace Suites by Marriott Winchester](//images.trvl-media.com/lodging/3000000/2750000/2745600/2745505/c096d0d5_y.jpg)

### TownePlace Suites by Marriott Winchester

10/10 Excellent

"Nice place to stay. Great staff and breakfast."

[](https://expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Winchester.h2745505.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"

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

![Skyland](//images.trvl-media.com/lodging/1000000/430000/421600/421517/5622bc24_y.jpg)

### Skyland

10/10 Excellent

"Rustic on the outside and blends in with nature. Clean and tidy on the inside and looks to be recently renovated. Bathroom was clean and spacious. Beautiful view overlooking Luray at night. We plan to stay two nights next time. Front desk was efficient, polite and professional. "

[](https://expedia.ca/Luray-Hotels-Skyland.h421517.Hotel-Information)

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

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Close to route 81"

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

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

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

10/10 Excellent

"Very nice lady at check in "

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

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

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

10/10 Excellent

"Always enjoy our stay at the GW Hotel. We were upgraded to a Junior Suite with a jacuzzi tub — an added bonus! It is conveniently located just a short walk to the pedestrian only downtown shops and restaurants. We will surely return when we are in the area."

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

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

### Comfort Inn & Suites Winchester

10/10 Excellent

"Excellent staff every time we stay!!"

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

## Find out more about Winchester

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Winchester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $147 per night. Entering your travel dates in the search wizard you might find even better deals!

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

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

-   [Vacation Homes in Winchester](https://expedia.ca/Winchester-Private-Vacation-Homes.d6056879-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Cabin Rentals in Winchester](https://expedia.ca/Winchester-Cabins.d6056879-aaCabins.Travel-Guide-Accommodation)
-   [Apartments in Winchester](https://expedia.ca/Winchester-Apartments.d6056879-aaApartments.Travel-Guide-Accommodation)
-   [Cottages in Winchester](https://expedia.ca/Winchester-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation)
-   [Chalets in Winchester](https://expedia.ca/Winchester-Chalets.d6056879-aaChalets.Travel-Guide-Accommodation)
-   [Farmstay in Winchester](https://expedia.ca/Winchester-Agritourism.d6056879-aaAgritourism.Travel-Guide-Accommodation)
-   [B&B in Winchester](https://expedia.ca/Winchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Motels in Winchester](https://expedia.ca/Winchester-Motels.d6056879-aaMotels.Travel-Guide-Accommodation)
-   [Guest Houses in Winchester](https://expedia.ca/Winchester-Guest-Houses.d6056879-aaGuestHouses.Travel-Guide-Accommodation)
-   [Villas in Winchester](https://expedia.ca/Winchester-Villas.d6056879-aaVillas.Travel-Guide-Accommodation)
-   [Lodges in Winchester](https://expedia.ca/Winchester-Lodges.d6056879-aaLodges.Travel-Guide-Accommodation)
-   [Resorts in Winchester](https://expedia.ca/Winchester-Resort-Hotels.d6056879-aaResortHotels.Travel-Guide-Accommodation)
-   [RV Parks in Winchester](https://expedia.ca/Winchester-RV-Parks.d6056879-aaRVParks.Travel-Guide-Accommodation)
-   [Condo Rentals in Winchester](https://expedia.ca/Winchester-Condos.d6056879-aaCondos.Travel-Guide-Accommodation)
-   [Inns in Winchester](https://expedia.ca/Winchester-Inns.d6056879-aaInns.Travel-Guide-Accommodation)
-   [Aparthotels in Winchester](https://expedia.ca/Winchester-Apart-Hotels.d6056879-aaApartHotels.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

> Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

### What are some of the best vacation home rentals in Winchester?

> [Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub](https://www.expedia.ca/Rileyville-Hotels-Lone-Bear-Cabin-Lv2-EV.h37274339.Hotel-Information): This vacation home near Winchester is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

### How many vacation rentals will I find in Winchester?

> Choose from 16 Expedia vacation rentals in Winchester for a memorable vacation.

### What’s there to see and do in Winchester?

> Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

### What’s a vacation rental in Winchester like?

> A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.

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-   [Flights to WAS](https://expedia.ca/Cheap-Flights-To-Alexandria.d5980.Travel-Guide-Flights)
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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)