Title: Winchester Vacation Rentals from CA $288: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/e4739be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/ccd121a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/33aedc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury tiny home farm stay on historic property with hot tub in Stephens City

[](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

Stephens City

10/10

Exceptional

(1 review)

"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "

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

Chris F.

CA $178

CA $224 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/13365e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/c5c32d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Bungalow in Front Royal

[](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

Front Royal

10/10

Exceptional

(13 reviews)

"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"

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

Brian B.

CA $185

CA $301 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/7f22680b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/d5eb0f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/0c0a82ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/212d2c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Front Royal

10/10

Exceptional

(5 reviews)

"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 $153

CA $503 total

includes taxes & fees

Feb 18 - Feb 19

[](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/114000000/113280000/113270800/113270721/32fe1fbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/706c1a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/aba028a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/58eee7b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  3BDR, 3 Full-Bath house in City, 2 living rooms \[3,000 sq. ft.\] - Pet Friendly!

[](https://www.expedia.ca/Stephens-City-Hotels-3BDR.h113270721.Hotel-Information)

Stephens City

9.4/10

Exceptional

(8 reviews)

"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "

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

Maureen W.

CA $176

CA $430 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Stephens-City-Hotels-3BDR.h113270721.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1136h1516x18y15-0867a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1129h841x0y0-0b4a0cfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1133h1513x0y23-fd248447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/a601c23d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rosamond nice downtown studio apt 

[](https://www.expedia.ca/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information)

Winchester Historic District

8.0/10

Very good

(2 reviews)

"Small but appropriately priced."

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

John M.

CA $150

CA $263 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.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)

![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Front Royal

10/10

Exceptional

(15 reviews)

"We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!"

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

Dan P.

CA $201

CA $561 total

includes taxes & fees

Mar 2 - Mar 3

[](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/84000000/83600000/83591200/83591191/9afb48f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/4e3d8e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/649fbfb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/3e63ad06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lunar Loft, with mountain views

[](https://www.expedia.ca/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

Bluemont

8.8/10

Excellent

(6 reviews)

"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "

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

Haley M.

CA $185

CA $373 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/92815ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/d94ec148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/f9fe7afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/16f6f354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Mountain Cabin, secluded, perfect for couples, near main road

[](https://www.expedia.ca/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information)

Front Royal

10/10

Exceptional

(28 reviews)

"Clean,Comfy, cozy, secluded and quiet!!! Perfect spot for a little getaway!"

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

Morgan S.

CA $246

CA $308 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/13764d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/4a787ba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/fa4984f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, stereo](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/2e3f9865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Bluemont Village Home

[](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information)

Bluemont

10/10

Exceptional

(39 reviews)

"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"

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

Mary S.

CA $240

CA $621 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Winchester-Hotels-Historic-Cottage-In-Bluemont-Village-VA-Wine-Country.h63112784.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/5441842b.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/90000000/89800000/89794800/89794757/1df4120a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/ed3e6638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly renovated Farm cottage with Mountain views 

[](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

Strasburg

10/10

Exceptional

(38 reviews)

"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "

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

Shannon H.

CA $219

CA $446 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/w1206h803x0y1-c15e243f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/5a0576c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/468501e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/37c783cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Haven at Turkey Run • Hot Tub, Fire Pit, Games

[](https://www.expedia.ca/Strasburg-Hotels-The-Haven-At-Turkey-Run-Hot-Tub.h104379779.Hotel-Information)

Strasburg

10/10

Exceptional

(11 reviews)

"Loved the creek and the hot tub!!! Cant say enough good things about this place"

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

Maxx H.

CA $232

CA $618 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Strasburg-Hotels-The-Haven-At-Turkey-Run-Hot-Tub.h104379779.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w506h683x260y0-1afec896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/3aaa43b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/w507h683x259y0-313a4f70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119540000/119530500/119530464/ff2d50c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Very charming & spacious 2 bedrm

[](https://www.expedia.ca/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

Winchester

CA $123

CA $238 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Winchester-Hotels-Very-Charming-Spacious-2-Bedrm.h119530464.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/fa314ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/0ff0b53d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/dc83b2f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/adf7c69e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy A frame cabin in quaint Front Royal. Dog friendly

[](https://www.expedia.ca/Front-Royal-Hotels-Cozy-A-Frame-Cabin-In-Quaint-Front-Royal-Dog-Friendly.h123436078.Hotel-Information)

Front Royal

10/10

Exceptional

(3 reviews)

"Had a good time during my stay and loved seeing Shenandoah"

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

Kye Y.

CA $201

CA $391 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Front-Royal-Hotels-Cozy-A-Frame-Cabin-In-Quaint-Front-Royal-Dog-Friendly.h123436078.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/547de25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/765a953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/38fc952e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/6e61e0ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yellow Submarine trendy basement apt and courtyard

[](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information)

Old Town Winchester

7.6/10

Good

(4 reviews)

"We loved the character and personality kf both Winchester and"

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

Jenna N.

CA $200

CA $355 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-And-Courtyard.h75856721.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/f4f1e4c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/ce9c558b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/a2b0b493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/ebfb0908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lamontagne Farmhouse a Rural Pristine Setting

[](https://www.expedia.ca/Bluemont-Hotels-Lamontagne-Farmhouse-A-Rural-Pristine-Setting.h69653828.Hotel-Information)

Bluemont

10/10

Exceptional

(12 reviews)

"We loved our stay at this beautiful tranquil farmhouse. Our two Golden’s enjoyed the outdoor space. Hiking close by, a beautiful drive to visit Middleburg is a must. We highly recommend this charming getaway."

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

AnneMarie M.

CA $98

CA $287 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Bluemont-Hotels-Lamontagne-Farmhouse-A-Rural-Pristine-Setting.h69653828.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/94ade5e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/4d2e26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/7a807893.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/233346bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

[](https://www.expedia.ca/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

Linden

9.4/10

Exceptional

(13 reviews)

"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"

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

Bret L.

CA $186

CA $490 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Linden-Hotels-Cute-Cabin-Retreat-Near-Shenandoah-National-Park-And-Pet-Friendly.h96487982.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/a1cdbec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/4d5adcbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/fac5b632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/7089a654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Juniper Cabin • Cozy Hideaway w/ Hot Tub

[](https://www.expedia.ca/Linden-Hotels-The-Juniper-Cabin-Cozy-Hideaway-W-Hot-Tub.h91195541.Hotel-Information)

Linden

10/10

Exceptional

(22 reviews)

"We had a fantastic time staying at this property for the weekend."

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

Colin N.

CA $171

CA $507 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Linden-Hotels-The-Juniper-Cabin-Cozy-Hideaway-W-Hot-Tub.h91195541.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/7b5c04b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/480b1e8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/bba48e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/e5066de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

[](https://www.expedia.ca/Front-Royal-Hotels-The-Honeymoon-Cabin-Private-Couples-Retreat-W-Hot-Tub.h113027243.Hotel-Information)

Front Royal

9.4/10

Exceptional

(3 reviews)

"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"

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

Paul B.

CA $268

CA $627 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Front-Royal-Hotels-The-Honeymoon-Cabin-Private-Couples-Retreat-W-Hot-Tub.h113027243.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/3a15610b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/e9d00149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/f205a55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/0debe0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shenandoah Twilight | Cozy Cabin w/ hot tub

[](https://www.expedia.ca/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.Hotel-Information)

Front Royal

9.0/10

Wonderful

(2 reviews)

"Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. "

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

Wilson (Wally) W.

CA $274

CA $618 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/c7a94a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/1b928033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nostalgia Lane in the heart of the city

[](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

Old Town Winchester

9.0/10

Wonderful

(15 reviews)

"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."

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

Tracy F.

CA $253

CA $459 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information)

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&regionId=6056879&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CABIN)

Cottages

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=COTTAGE)

Private vacation homes

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=VACATION_HOME)

Apartments

[](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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=APARTMENT)

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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&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=2026-05-10&d1=2026-05-10&endDate=2026-05-13&d2=2026-05-13&lodging=CHALET)

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## Top Winchester Hotel Reviews

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

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

10/10 Excellent

"All good"

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

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

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

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

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

### Holiday Inn Express Charles Town by IHG

10/10 Excellent

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

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

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

### Travelodge by Wyndham Winchester

10/10 Excellent

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

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

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

### Mimslyn Inn Historic Hotels Of America

10/10 Excellent

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

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

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

### Comfort Inn & Suites Winchester

10/10 Excellent

"The room was spotless , and the staff was very curtis"

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

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

### Hilton Garden Inn Dulles North

10/10 Excellent

"Clean room,.nice staff, large walk-in shower, coffee maker and mini fridge! Great price, saved 20 bucks online with Expedia app! I will definitely come back for another "staycation" "

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

"Room was very clean and spacious, staff was wonderful!"

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

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

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

10/10 Excellent

"The staff was wonderful! "

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

## Find out more about Winchester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [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)
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- [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)
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- [Condo Rentals in Winchester ](https://expedia.ca/Winchester-Condos.d6056879-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

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

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

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- [Best Hotels in Wytheville](https://expedia.ca/Wytheville-Hotels.d6056934.Travel-Guide-Hotels)
- [Virginia Beach Hotels with Kitchenettes](https://expedia.ca/Virginia-Beach-Hotels-Hotels-With-Kitchenettes.0-0-d10271-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels)
- [Best Hotels in Harrisonburg](https://expedia.ca/Harrisonburg-Hotels.d6056902.Travel-Guide-Hotels)
- [Best Hotels in Charlottesville](https://expedia.ca/Charlottesville-Hotels.d6057012.Travel-Guide-Hotels)
- [Best Hotels in Alexandria](https://expedia.ca/Alexandria-Hotels.d5980.Travel-Guide-Hotels)
- [Best Hotels in Fairfax](https://expedia.ca/Fairfax-Hotels.d8062.Travel-Guide-Hotels)
- [Best Hotels in Petersburg](https://expedia.ca/Petersburg-Hotels.d9485.Travel-Guide-Hotels)
- [Best Hotels in Roanoke](https://expedia.ca/Roanoke-Hotels.d3020.Travel-Guide-Hotels)
- [Best Hotels in Virginia Beach](https://expedia.ca/Virginia-Beach-Hotels.d10271.Travel-Guide-Hotels)

Flights

- [Flights to PHF](https://expedia.ca/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
- [Flights to WAS](https://expedia.ca/Cheap-Flights-To-Alexandria.d5980.Travel-Guide-Flights)
- [Flights to ROA](https://expedia.ca/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights)
- [Flights to DCA](https://expedia.ca/Cheap-Flights-To-Syria.d184113.Travel-Guide-Flights)
- [Flights to CHO](https://expedia.ca/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights)

Activities

- [Things to do in Williamsburg](https://expedia.ca/Things-To-Do-In-Williamsburg.d6296.Travel-Guide-Activities)
- [Things to do in Reston](https://expedia.ca/Things-To-Do-In-Reston.d10437.Travel-Guide-Activities)
- [Things to do in Virginia Beach](https://expedia.ca/Things-To-Do-In-Virginia-Beach.d10271.Travel-Guide-Activities)
- [Things to do in Norfolk](https://expedia.ca/Things-To-Do-In-Norfolk.d2689.Travel-Guide-Activities)

Packages

- [Flight and Hotel Virginia Beach](https://expedia.ca/Virginia-Beach.d10271.Destination-Travel-Guides)
- [Flight and Hotel Swoope](https://expedia.ca/Swoope.d3000460689.Destination-Travel-Guides)

Vacation Rentals

- [Virginia Beach Short Term Rentals](https://expedia.ca/Virginia-Beach-Vacation-Rentals.d10271.Travel-Guide-VacationRentals)

General

- [Visit Virginia Beach](https://expedia.ca/Virginia-Beach.dx10271)

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