Title: Winchester Vacation Home Rentals from CA $290: Search Top Private Vacation Homes for Rent | Expedia.ca

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# Winchester Vacation Rentals

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## Check prices for these dates

Next weekend

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

In two weeks

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

In one month

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

## Our top choices for Winchester vacation homes

![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)

![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)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.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)

### 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

(11)

"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 $186

CA $302 total

includes taxes & fees

Dec 13 - Dec 14

[](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)

![Interior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/8e6ba5b7.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 $221

CA $447 total

includes taxes & fees

Dec 14 - Dec 15

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

![Smart TV, foosball](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/8a0bbbc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/32fe1fbb.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)

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/aba028a8.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

9.2/10

Wonderful

(7)

"Our stay here was outstanding. The house was clean, spacious, and close to many shops/restaurants. Our first evening we spent in downtown Winchester which was an easy drive from the home. The next day was spent at the Virginia Scottish Games, about 35 minutes away. The house was definitely worth the stay! We had a great time. It was even one of the best smelling houses we had ever rented! 100% recommend and would stay again. "

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

Ashley B.

CA $178

CA $437 total

includes taxes & fees

Dec 17 - Dec 18

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/a696274d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/9641cad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/64000000/63120000/63112800/63112784/ed3d2da3.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)

"No need to look any further! Beautiful, clean,historic home in a perfect location. Close to wineries, breweries, Shenandoah River, hiking and only 45 minutes from DC. The host was very accommodating and friendly as well. We would highly recommend this home for you and your family. "

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

Brian and Allison W.

CA $217

CA $587 total

includes taxes & fees

Dec 14 - Dec 15

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

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/58d98b30.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)

![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)

### 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 $241

CA $555 total

includes taxes & fees

Dec 13 - Dec 14

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/ab6df544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/w1184h883x3y0-95d19d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/cb8a9693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87980000/87973200/87973124/abe2d599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

[](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.Hotel-Information)

Linden

10/10

Exceptional

(20)

"View was great, was pretty isolated from other houses in the area, and cute decor. Very comfortable stay. "

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

Andrew G.

CA $232

CA $502 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Linden-Hotels-Hottub.h87973124.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)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/6b5ccc9e.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)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75857000/75856945/1ca53946.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 $273

CA $481 total

includes taxes & fees

Dec 14 - Dec 15

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

![Dining](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/43d2da0f.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)

![Interior](https://images.trvl-media.com/lodging/85000000/84090000/84086300/84086243/c61d77dc.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 $225

CA $585 total

includes taxes & fees

Jan 12 - Jan 13, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/2736c2e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/ef522d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, stovetop](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/93b157cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121420000/121418500/121418475/dda7ab71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Riverfront Home Getaway with Hot Tub

[](https://www.expedia.ca/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information)

Warren County

CA $301

CA $647 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Front-Royal-Hotels-Luxury-Riverfront-Home-Getaway-With-Hot-Tub.h121418475.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/a448a4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/9221f31b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/73acc693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/fcd07d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom!

[](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

Front Royal

8.8/10

Excellent

(30)

"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"

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

Mollie S.

CA $233

CA $416 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/6f72fa61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/2032cec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/ea0185a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/8aa3fa94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Apple Mountain House

[](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information)

Front Royal

9.6/10

Exceptional

(9)

"Amazing place to relax."

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

Edna K.

CA $139

CA $481 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/88fd6b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/25a34129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/c04a2393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118360000/118355600/118355581/6278c5db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

[](https://www.expedia.ca/Linden-Hotels-Cozy-Luxury.h118355581.Hotel-Information)

Linden

10/10

Exceptional

(3)

"Megan was exceptional at communications, the property was perfect for our Family Thanksgiving. "

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

Lynne S.

CA $394

CA $745 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Linden-Hotels-Cozy-Luxury.h118355581.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/512057d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/df4a0d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/de9610ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120450000/120444500/120444425/89b2ef24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Front royal majestic paradise

[](https://www.expedia.ca/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.Hotel-Information)

Front Royal

CA $1,655

CA $2,126 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Front-Royal-Hotels-Front-Royal-Majestic-Paradise.h120444425.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/87000000/86340000/86332000/86331916/c265bcd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/87000000/86340000/86332000/86331916/15f20b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/87000000/86340000/86332000/86331916/42c7fa2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/87000000/86340000/86332000/86331916/6ea3043d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deer Trail Cabin \~ Mtn views \~ Firepit \~ Hiking

[](https://www.expedia.ca/Luray-Hotels-Deer-Trail-Cabin-Mtn-Views-Firepit-Hiking.h86331916.Hotel-Information)

Luray

9.4/10

Exceptional

(22)

"Nice property in a nice location. "

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

Wayne B.

CA $207

CA $417 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Luray-Hotels-Deer-Trail-Cabin-Mtn-Views-Firepit-Hiking.h86331916.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/d64b9ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/046a30f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/95da1211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/98000000/97590000/97582200/97582140/611a040d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful Retreat on Creekside

[](https://www.expedia.ca/Edinburg-Hotels-Peaceful-Retreat-On-Creekside.h97582140.Hotel-Information)

Edinburg

9.6/10

Exceptional

(15)

"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "

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

Richard D.

CA $129

CA $290 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Edinburg-Hotels-Peaceful-Retreat-On-Creekside.h97582140.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/88000000/87920000/87912000/87911941/a5bc34e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87920000/87912000/87911941/03afc87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87920000/87912000/87911941/663099e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87920000/87912000/87911941/43c632d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Blue Pearl by Zen Living

[](https://www.expedia.ca/Luray-Hotels-The-Blue-Pearl-By-Zen-Living.h87911941.Hotel-Information)

Luray

10/10

Exceptional

(11)

"The Blue Pearl is a wonderful spot in Luray! It is in a wonderful location just minutes away from Luray Caverns, Shenandoah National Park, wineries, and the Main Street for cafes and restaurants. The home was exactly as pictured, clean, well equipped for all of our needs, and welcoming to our fur-baby. Jason was incredibly kind and communicative. This home will be our stay-of-choice whenever we return to the area! "

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

Mary S.

CA $135

CA $394 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Luray-Hotels-The-Blue-Pearl-By-Zen-Living.h87911941.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119680000/119672800/119672727/abd50833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119680000/119672800/119672727/ff13635b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119680000/119672800/119672727/df060ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119680000/119672800/119672727/69e04f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wooded Nest, Cozy 3BR Chalet Near Spas & Hiking

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Wooded-Retreat.h119672727.Hotel-Information)

Berkeley Springs

10/10

Exceptional

(2)

"We had a blast! Great place, stocked with everything you need, hot tub was perfect, safe for small kids and close to town! "

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

Nicole W.

CA $170

CA $527 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Wooded-Retreat.h119672727.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/354e36e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/dbbf789b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/529562ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106270000/106262900/106262808/57cbb436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

[](https://www.expedia.ca/Luray-Hotels-Peaceful-Cottage-In-Farmland-4-Miles-To-Luray9-Miles-To-ShenNatl-Park.h106262808.Hotel-Information)

Luray

10/10

Exceptional

(12)

"Great stay- only one night for a friends wedding in Shenandoah. Nice place to stay, no issues! "

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

Jacquelin S.

CA $200

CA $390 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Luray-Hotels-Peaceful-Cottage-In-Farmland-4-Miles-To-Luray9-Miles-To-ShenNatl-Park.h106262808.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90800000/90791800/90791716/c3f31091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90800000/90791800/90791716/2677f99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90800000/90791800/90791716/0270c5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90800000/90791800/90791716/05ffe1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern, family-friendly, nature packed getaway

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Modern.h90791716.Hotel-Information)

Berkeley Springs

9.2/10

Wonderful

(19)

"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "

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

Erika R.

CA $173

CA $373 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Modern.h90791716.Hotel-Information)

![Smart TV, Hulu, streaming services](https://images.trvl-media.com/lodging/82000000/81290000/81286100/81286079/8c9bb7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, Hulu, streaming services](https://images.trvl-media.com/lodging/82000000/81290000/81286100/81286079/59f54910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/82000000/81290000/81286100/81286079/acfd4d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/82000000/81290000/81286100/81286079/66e44c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

[](https://www.expedia.ca/Luray-Hotels-Tiny-Barn-WModern-Charm-On-3-Acres.h81286079.Hotel-Information)

Luray

10/10

Exceptional

(64)

"Ideal location "

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

Jeremiah B.

CA $124

CA $310 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Luray-Hotels-Tiny-Barn-WModern-Charm-On-3-Acres.h81286079.Hotel-Information)

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

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## Find vacation rentals that suit your style

Cabins

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Apartments

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Private vacation homes

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Villas

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

Chalets

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## Top Winchester Hotel Reviews

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Comfortable and clean room."

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

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

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

10/10 Excellent

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

[](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information)

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

### Travelodge by Wyndham Winchester

10/10 Excellent

"Room clean, heater works great parking "

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

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

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

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

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

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

### Quality Inn Winchester

10/10 Excellent

"Everything was great, including breakfast "

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

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

### Hampton Inn Martinsburg

10/10 Excellent

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

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

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

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

10/10 Excellent

"Super friendly reception and perfectly clean room. "

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

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

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

10/10 Excellent

"Staff is fantastic and breakfast is always great. "

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

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

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

10/10 Excellent

"Clean room, easy and quick check in."

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

## Find out more about Winchester

## Winchester Vacation Homes information

| Number of reviews | 336                |
| ----------------- | ------------------ |
| Accommodation     | 632 Vacation Homes |
| Lowest Price      | CA $290            |
| Highest Price     | CA $2,126          |

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- [Old Town Winchester Hotels ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)
- [Hotels near Patsy Cline Historic House ](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels)
- [Lodges in Riverton ](https://www.expedia.ca/Riverton-Lodges.d553248635975849884-aaLodges.Travel-Guide-Accommodation)
- [Hotels near Rock Harbor Golf Course ](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels)
- [Cottages in Shawnee Land ](https://www.expedia.ca/Shawnee-Land-Cottages.d553248635975849755-aaCottages.Travel-Guide-Accommodation)
- [Hotels near Shenandoah University ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels)
- [Hotels near State Arboretum of Virginia ](https://www.expedia.ca/State-Arboretum-Of-Virginia-Hotels.0-l6164038-0.Travel-Guide-Filter-Hotels)
- [B&B in Stephens City ](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Historic Hotels in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels)
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- [Stephens City Hotels ](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels)
- [Hotels near Valerie Hill Winery ](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels)
- [Honeymoon Resorts and in White Post ](https://www.expedia.ca/White-Post-Hotels-Honeymoon-Hotels.0-0-d184119-tHoneymoonHotels.Travel-Guide-Filter-Hotels)
- [White Post Hotels ](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels)
- [Hotels near Winchester-Frederick County Convention & Visitors Bureau ](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels)
- [Hotels with Bar in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Hotels-With-Bar.0-n918789051029594112-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
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- [Spa Hotels in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Spa-Hotel.0-n918789051029594112-0-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Hotels near Winchester Medical Center ](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels)

- [Flights to Boyce ](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights)
- [Flights to Millwood ](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights)
- [Flights from Winchester Regional ](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport)
- [Flights from Gore ](https://www.expedia.ca/lp/flights/3000460015/flights-from-gore)
- [Flights from Clear Brook ](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook)
- [Flights from Blacksburg (BCB) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester)
- [Flights from Hartford (BDL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester)
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- [Flights from Denver (DEN) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester)
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- [Flights from El Paso (ELP) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester)
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- [Flights from Greenville (GSP) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester)
- [Flights from Jacksonville (JAX) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester)
- [Flights from Melbourne (MEL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester)
- [Flights from Sarasota (SRQ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester)
- [Flights from Syracuse (SYR) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester)
- [Flights from Calgary (YYC) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester)
- [Flights from Toronto (YYZ) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester)

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

- [Book Vacation Homes in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Private-Vacation-Homes.d6056879-aaPrivateVacationHomes.Travel-Guide-Accommodation)