Title: Winchester Vacation Rentals from CA $143: Short-Term Rentals for 2026 | Expedia.ca

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# Winchester Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-04-17&endDate=2026-04-19&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

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

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/10e90959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108370000/108361400/108361347/f428f0b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### 1800s Cozy Kitchen House in Berryville

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

Berryville

10/10

Exceptional

(1)

"This unique gem was resurrected and rebirthed. It screams creativity and provides all of the comforts of home with the perfect balance between modern conveniences and days of yore. Great location for Harper’s Ferry goers. Definitely cannot say enough good things because it’s one helluva of a place to rest."

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

Kelly G.

CA $197

CA $252 total

includes taxes & fees

Dec 27 - Dec 28

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

![Property grounds](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/d3302e05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/23f4000c.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)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/234bd7f2.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

CA $178

CA $224 total

includes taxes & fees

Jan 1 - Jan 2, 2026

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

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1118h1128x0y0-c29ed3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1136h1516x18y15-0867a003.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/w1129h841x0y0-0b4a0cfb.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)

"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

Jan 1 - Jan 2, 2026

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

![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)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/435bb49d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/31231b11.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

(25)

"Great place to relax"

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

Judy

CA $246

CA $303 total

includes taxes & fees

Dec 29 - Dec 30

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

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/32a5f0df.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/928d407e.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

(12)

"My husband and I stayed here for a short weekend vacation in Shenandoah. It’s a very cute, clean, and cozy home. We loved the front porch and the view. We had a small mishap with our combination when we first arrived, but the host was very quick to respond and it was resolved in only a few minutes. My husband and I would both stay here again! "

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

sara h.

CA $185

CA $300 total

includes taxes & fees

Dec 28 - Dec 29

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

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/15fd4469.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/bc1a175e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/2f2ce964.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)

### 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)

"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 $443 total

includes taxes & fees

Dec 28 - Dec 29

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

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/59a5c7fc.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)

### "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

(3)

"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 $206

CA $564 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/e90c6032.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)

### Private apartment on a beautiful private farm!

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

Bluemont

8.8/10

Excellent

(6)

"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 $369 total

includes taxes & fees

Jan 5 - Jan 6, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/5723463e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/83d3573f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/c1fdc4b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/124000000/123440000/123436100/123436078/84ae0843.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

CA $178

CA $363 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/b9f5910e.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/97000000/96490000/96488000/96487982/9df5c033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, paper towels](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/37df05c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/97000000/96490000/96488000/96487982/92d8a360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cute cabin retreat near Shenandoah National Park and pet friendly!

[](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)

"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 $181

CA $482 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

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

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

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.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

9.8/10

Exceptional

(10)

"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 $199

CA $494 total

includes taxes & fees

Jan 12 - Jan 13, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/01fca712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/6b26f42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/2ce760e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105770000/105765500/105765423/dce8d0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall 

[](https://www.expedia.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information)

Winchester Historic District

8.6/10

Excellent

(4)

"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."

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

matthew r.

CA $189

CA $315 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Winchester-Hotels-Dreamweaver-1BR-1BA-Just-Two-Blocks-From-The-Downtown-Walking-Mall.h105765423.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/a4ec224c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/1ca53946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/396388c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/cbf483db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cameron Charmer pristine downtown apt with double master suites 

[](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

Winchester

9.4/10

Exceptional

(6)

"Nice house in a good central location. "

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

Mitchell V.

CA $271

CA $482 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Winchester-Hotels-Cameron-Charmer-Pristine-Downtown-Apt-With-Double-Master-Suites.h75856945.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/10901b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/48aeb310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/b7a39e49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/4f7ea815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apple Mountain Retreat

[](https://www.expedia.ca/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information)

Linden

10/10

Exceptional

(21)

"Great place to stayed "

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

Mike F.

CA $185

CA $320 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Linden-Hotels-Apple-Mountain-Retreat.h104052857.Hotel-Information)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/91000000/90300000/90291900/90291822/f4ac651d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90300000/90291900/90291822/42b03ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/91000000/90300000/90291900/90291822/a27c3297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90300000/90291900/90291822/4a45a3db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to Shenandoah River, Hot Tub after a Hike! 

[](https://www.expedia.ca/Front-Royal-Hotels-New-Sapphire-Ridge-Escape-To-Shenandoah-River-Hot-Tub.h90291822.Hotel-Information)

Front Royal

10/10

Exceptional

(55)

"Its a nice property to stay. Will be back soon "

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

Faizan A.

CA $184

CA $479 total

includes taxes & fees

Jan 20 - Jan 21, 2026

[](https://www.expedia.ca/Front-Royal-Hotels-New-Sapphire-Ridge-Escape-To-Shenandoah-River-Hot-Tub.h90291822.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/43e19b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/5e1231b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/9ba529c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75854400/75854350/w1080h1606x0y6-7da3475e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Stock Exchange downtown 3rd floor studio apt

[](https://www.expedia.ca/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information)

Winchester Historic District

6.0/10

(1)

CA $150

CA $271 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Winchester-Hotels-The-Stock-Exchange-Downtown-3rd-Floor-Studio-Apt.h75854350.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/be8b72ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/5e14b0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/2824c15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/70000000/69660000/69653900/69653828/0d127cc3.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

(11)

"Had every thing we needed."

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

Joanna T.

CA $185

CA $396 total

includes taxes & fees

Dec 30 - Dec 31

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

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/434367ca.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)

![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/4cf065b7.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)

### 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

(14)

"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 $454 total

includes taxes & fees

Dec 28 - Dec 29

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/23f46f24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/b0176d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/c61d77dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/ccb9b8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big Sunny Family House

[](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.Hotel-Information)

Front Royal

10/10

Exceptional

(40)

"Wonderful house and town! Loved every minute of our trip! "

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

MaryAnn G.

CA $212

CA $557 total

includes taxes & fees

Jan 26 - Jan 27, 2026

[](https://www.expedia.ca/Front-Royal-Hotels-Big-House.h84086243.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x1y1-de179e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x0y1-34023d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w3000h2002x0y1-874ebd45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2998h2002x1y1-e4dac9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Welcome to the Ladybug Retreat!

[](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information)

Boyce

10/10

Exceptional

(1)

"This home is lovely and the host has thought of everything. We will definitely stay here again. "

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

Catherine A.

CA $239

CA $552 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.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

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

### Hampton Inn Martinsburg

10/10 Excellent

"Nice room"

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

"Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!"

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

"The breakfast staff is helpful "

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

![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg)

### SpringHill Suites by Marriott Winchester

10/10 Excellent

"Great location, clean, safe, plenty of free parking and quiet, comfortable and spacious room."

[](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information)

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

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

10/10 Excellent

"It would be nice if they had a business center that was actually a business center and not a storage room"

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

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

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

10/10 Excellent

"Clean and quiet"

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

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

### TRU By Hilton Winchester

10/10 Excellent

"Effortless check-in. Clean quiet room. Friendly staff"

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

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

### TownePlace Suites by Marriott Winchester

10/10 Excellent

"Great place to rest. Clean and family/pet friendly. "

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

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

### Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent

"Courteous staff, clean room. 🙂 "

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

## 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)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d6056879-aaInns.Travel-Guide-Accommodation)
- [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?

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

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

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

### Expedia's Latest Trends

Hotels

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Flights

- [Flights to PHF](https://expedia.ca/Cheap-Flights-To-Hampton.d6067.Travel-Guide-Flights)
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- [Flights to PHF](https://expedia.ca/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
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Activities

- [Things to do in Virginia Beach](https://expedia.ca/Things-To-Do-In-Virginia-Beach.d10271.Travel-Guide-Activities)
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Packages

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

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

General

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