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

 

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# Winchester Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

In three months

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

In four months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6056879&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Winchester

![Exterior](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/e75c3693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/bc11097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/w1284h952x0y7-6504b025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/39677a93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy English Basement Apt quiet but close to downtown

Winchester

9.6/10

Exceptional

(7)

"Friendly owner. Came over when I couldn't start the pilot light on the gas wall heater. A few blocks away from some excellent restaurants in the historic district. It's in a remodeled basement with air ducts so head clearance is limited for tall folk."

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

Dale

CA $140

CA $247 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Winchester-Hotels-Cozy-English-Basement-Apt-Quiet-But-Close-To-Downtown.h75832325.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)

![Exterior](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/0b0b85aa.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, 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

Stephens City

CA $183

CA $230 total

includes taxes & fees

Nov 11 - Nov 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)

![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/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/b8a5d193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Front Royal

10/10

Exceptional

(2)

"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 $184

CA $552 total

includes taxes & fees

Nov 18 - Nov 19

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

![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/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)

![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

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 $154

CA $271 total

includes taxes & fees

Nov 13 - Nov 14

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

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/56f94878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/4793a0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/07dac09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/7c5e3f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Historic Schoolhouse HotTub+FirePit+Wineries

Fauquier County

8.0/10

Very good

(1)

"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...

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

Kathy S.

CA $126

CA $395 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/a47a043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/5028cd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/d8cde914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/4de2ef6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

10/10

Exceptional

(2)

"Had a fun visit. Property and host we're excellent."

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

Daniel D.

CA $171

CA $353 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Bluemont-Hotels-Stylish-1-Bd1-Ba-Gardern-Apt-Within-Quaint-Bluemont-Village.h118716576.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/2ca3d794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/70f721a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/9a2a0e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/88000000/87560000/87551300/87551282/20a8dae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin Retreat in Virginia Wine Country • Hot Tub, Theatre & Game Room, & More

Linden

9.8/10

Exceptional

(10)

"We had a great stay in Delicious Cabin. The property was bigger than I thought, immactualtely clean and so quiet.The owner is very quick to respond to messages.The area is very peaceful, we felt completely relaxed after our stay. The cabin is very well stocked. the kitchen is really organised, the cupboards are all labelled which saved me time opening every cupboard to find something. Slept really well in the really comfortable beds. Bathrooms were stocked with shampoo etc too.The hot tub...

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

Annette S.

CA $166

CA $507 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Linden-Hotels-Delicious-Cabin-Hot-Tub.h87551282.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)

![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/97000000/96490000/96488000/96487982/9df5c033.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)

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

Linden

9.4/10

Exceptional

(12)

"The place was very clean. Fully stocked a great location and we would stay again"

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

Patty P.

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

![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)

### Mountain View Bungalow in Front Royal

Front Royal

10/10

Exceptional

(8)

"Excelente propiedad "

![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg)

Miguel

CA $190

CA $311 total

includes taxes & fees

Nov 11 - Nov 12

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

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/46b2345e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/02c6ece4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/f647e572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121940000/121935800/121935788/67ecaf82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Farm Suite at Valley View Farm

Delaplane

CA $183

CA $402 total

includes taxes & fees

Nov 11 - Nov 12

[](https://www.expedia.ca/Farm-Suite-At-Valley-View-Farm.h121935788.Hotel-Information)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/73aafe78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/f1a2a944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/b94fe33d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/358c6628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Skyland Hideaway • Relaxing Cabin w/ Hot Tub, Deck, Grill, & Fire table

Linden

10/10

Exceptional

(14)

"Quiet with amenities to support R&R, enjoying nature, and togetherness."

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

Patricia B.

CA $166

CA $490 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Linden-Hotels-Skyland-Hideaway-Mountain-Cabin-W-Hot-Tub.h87568647.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)

![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)

![Game room](https://images.trvl-media.com/lodging/114000000/113280000/113270800/113270721/w1049h1392x0y4-94176e01.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!

Stephens City

9.2/10

Wonderful

(7)

"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 $180

CA $442 total

includes taxes & fees

Nov 23 - Nov 24

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/17745535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/9b7a2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/a1533d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/0bb76882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Honeymoon Cabin | Private Retreat w/ hot tub

Front Royal

10/10

Exceptional

(1)

"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 $209

CA $543 total

includes taxes & fees

Nov 11 - Nov 12

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

![Exterior](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/533e235c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/72e06ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91200000/91195600/91195541/4e14b14a.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/ad31a208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Juniper Cabin • Private Hideaway w/ Hot Tub, Grill & Screened Porch

Linden

10/10

Exceptional

(22)

"Cozy, clean, close to fantastic hikes!"

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

Beth C.

CA $191

CA $503 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Linden-Hotels-Whitetail-Cabin-Couples-Retreat-W-Hot-Tub.h91195541.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)

![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)

### Private apartment on a beautiful private farm!

Bluemont

8.8/10

Excellent

(6)

"This little farm condo was absolutely perfect for our overnight stay. In fact, I wish we had the opportunity to stay longer. It was lovely to wake up and see chickens and other animals as well as hear the dogs barking. The view of the mountains was also lovely! We will definitely think of staying here again next time we visit our friends!"

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

Matthew S.

CA $190

CA $379 total

includes taxes & fees

Nov 11 - Nov 12

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/0039f8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/c4098929.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/bfc73b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104380000/104379800/104379779/093e34a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Haven at Turkey Run • 13-Acre Creekside Retreat w/ Hot Tub, Fire Pit, Games

Strasburg

10/10

Exceptional

(11)

"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 $221

CA $589 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Strasburg-Hotels-Secluded-Cabin-Escape-Hot-Tub-Games-13-Acres.h104379779.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)

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

### Historic Bluemont Village Home

Bluemont

10/10

Exceptional

(37)

"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 $228

CA $608 total

includes taxes & fees

Nov 11 - Nov 12

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

![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)

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

![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/fe22c400.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/76000000/75860000/75856800/75856721/f2a89cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yellow Submarine trendy basement apt and courtyard

Old Town Winchester

9.0/10

Wonderful

(2)

"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 $205

CA $361 total

includes taxes & fees

Nov 13 - Nov 14

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

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/4bba56d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/e1d5317e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/ce787f6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112550000/112549200/112549200/3bbb4cde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

Front Royal

10/10

Exceptional

(4)

"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "

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

grace g.

CA $217

CA $734 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Front-Royal-Hotels-The-Cozy-Bear-Cabin-Hot-Tub.h112549200.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)

![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.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)

![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)

### Newly renovated Farm cottage with Mountain views

Strasburg

10/10

Exceptional

(38)

"Very clean cottage with well-stocked kitchen with a great outdoors area for grilling and hanging out. Quiet relaxing location way up off the road. The hosts were unobtrusive but available. We have already recommended this cottage to our immediate family for future stays. "

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

Becky C.

CA $225

CA $457 total

includes taxes & fees

Nov 11 - Nov 12

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

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

### Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent

"Excellent accommodations"

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

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

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

10/10 Excellent

"Good"

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

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

### TRU By Hilton Winchester

10/10 Excellent

"The hotel was clean and the staff was pleasant."

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

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

### Spark by Hilton Winchester

10/10 Excellent

"The lobby had fun Halloween decorations and the front desk lady was very happy and kind. The room was perfect for me."

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

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

### Quality Inn Winchester

10/10 Excellent

"Very clean and confortable "

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

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

### Travelodge by Wyndham Winchester

10/10 Excellent

"Such a great find for our overnight Stay and last minute with excellent price. Comfortable bed and fantastic staff. Breakfast lacking but expected. "

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

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

### Candlewood Suites Winchester by IHG

10/10 Excellent

"From the girl who checked us in, the very clean room. Excellent service "

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

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

### Comfort Inn & Suites Winchester

10/10 Excellent

"It was the cleanest and most friendly place I’ve ever stayed at.The breakfast was amazing the beds were very comfortable hardly any noise just a great place to stay."

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

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

### La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Great in all ways. Fresh, modern hotel. Big rooms."

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

## Find out more about Winchester

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

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

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

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

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

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

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

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

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

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

## Explore a world of travel with Expedia

-   Trending destinations on Expedia.ca
-   All accommodation types in Winchester

### Trending destinations on Expedia.ca

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-   [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations)
-   [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations)
-   [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations)
-   [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

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

## Frequently asked questions

### Can I find vacation rentals in Winchester?

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

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

> Choose from 17 Expedia vacation rentals in Winchester for a memorable vacation.

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

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

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

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

### Expedia's Latest Trends

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Flights

-   [Flights to Hampton](https://expedia.ca/Cheap-Flights-To-Hampton.d6067.Travel-Guide-Flights)
-   [Flights to Lynchburg](https://expedia.ca/Cheap-Flights-To-Lynchburg.d2187.Travel-Guide-Flights)
-   [Flights to Virginia Beach](https://expedia.ca/Cheap-Flights-To-Virginia-Beach.d10271.Travel-Guide-Flights)
-   [Flights to Alexandria](https://expedia.ca/Cheap-Flights-To-Alexandria.d5980.Travel-Guide-Flights)
-   [Flights to Fairfax](https://expedia.ca/Cheap-Flights-To-Fairfax.d8062.Travel-Guide-Flights)
-   [Flights to Roanoke](https://expedia.ca/Cheap-Flights-To-Roanoke.d3020.Travel-Guide-Flights)
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-   [Flights to Charlottesville](https://expedia.ca/Cheap-Flights-To-Charlottesville.d6057012.Travel-Guide-Flights)

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

-   [Virginia Beach Vacations](https://expedia.ca/Virginia-Beach.d10271.Destination-Travel-Guides)
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-   [Virginia Beach Vacation 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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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

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

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