Title: Winchester B&B: Find the Best Bed and Breakfast from CA $196 | Expedia.ca

[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6056879.Destination-Travel-Guides)

![](https://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find a Bed and Breakfast in Winchester from CA $196

- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg)  
###  
Change your mind  
Book hotels with free cancellation
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg)  
###  
Treat yourself  
Sign in to save 10% or more on thousands of hotels  
[Sign in](https://www.expedia.ca/login)
- ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg)  
###  
Be picky  
Search almost a million properties worldwide

## 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&lodging=BED_AND_BREAKFAST&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&lodging=BED_AND_BREAKFAST&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&lodging=BED_AND_BREAKFAST&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&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester bed & breakfast

![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/6e95af26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/5536aedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/95f3e504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Windsor Suite) | Deep soaking bathtub](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/c20a2340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Glen Gordon Manor

[](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information)

Huntly

9.8/10

Exceptional

(94)

"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."

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

KYLE

CA $426

CA $466 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information)

![Interior detail](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/72d8a0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/fdad32ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/8458539f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/d7b2bbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gay Street Inn

[](https://www.expedia.ca/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information)

Washington

10/10

Exceptional

(34)

"Beautiful historic Inn with incredible owners and service. "

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

Renee

CA $495

CA $534 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information)

![Family House, Multiple Beds, Balcony, Garden Area | Balcony](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/5496a00d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/e996c5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House, Multiple Beds, Balcony, Garden Area | Private kitchen](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/1805c4e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/a8e8b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hopkins Ordinary Bed Breakfast and Ale Works

[](https://www.expedia.ca/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information)

Sperryville

10/10

Exceptional

(31)

"Great place. Good food, great beer."

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

Phil

[](https://www.expedia.ca/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information)

![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/acf14b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/a53cd216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carriage Inn B&B

[](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information)

Charles Town

9.6/10

Exceptional

(439)

"Excellent accommodations and breakfast. "

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

William

CA $173

CA $196 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/f3c32a81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/f1873da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/098eec3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/37000000/36140000/36132200/36132129/264bfdf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Loudoun Valley Manor

[](https://www.expedia.ca/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information)

Waterford

9.6/10

Exceptional

(276)

"Great location for visiting wineries"

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

Anne

CA $194

CA $222 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Waterford-Hotels-Loudoun-Valley-Manor.h36132129.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/3fe7c40a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Suite, 1 King Bed, Hot Tub, Mountain View](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/846a016e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/8f141c44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception hall](https://images.trvl-media.com/lodging/17000000/16290000/16281800/16281705/0aef02f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stone Manor Boutique Inn

[](https://www.expedia.ca/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information)

Lovettsville

9.6/10

Exceptional

(95)

"The experience was very good, will return in the future. The breakfast was excellent. "

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

Marvin

CA $264

CA $301 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Lovettsville-Hotels-Stone-Manor-Boutique-Inn.h16281705.Hotel-Information)

![Free daily full breakfast](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0869608f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Bridal Suite Room 260)](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/3a3f9489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/8659900e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/16000000/15740000/15733600/15733502/0932b9ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Evergreen

[](https://www.expedia.ca/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information)

Haymarket

9.4/10

Exceptional

(131)

"Clean,very nice facility "

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

Matthew P

[](https://www.expedia.ca/Haymarket-Hotels-Inn-At-Evergreen.h15733502.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/2f491ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/7918f369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Single Room, Mountain View](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/d88b46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/118000000/117730000/117723700/117723633/51165234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Grass Roots Hill

[](https://www.expedia.ca/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information)

Purcellville

9.2/10

Wonderful

(7)

"House and property are absolutely beautiful. Staff are amazing and super friendly "

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

Chad

CA $633

CA $721 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Purcellville-Hotels-The-Inn-At-Grass-Roots-Hill.h117723633.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/fc69b508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living room](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/119fee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living room](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/f7ffda1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/19000000/18670000/18669500/18669467/8c9de01c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cantuta Inn

[](https://www.expedia.ca/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information)

Harpers Ferry

9.0/10

Wonderful

(74)

"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "

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

Aleta

CA $221

CA $247 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Martinsburg-Hotels-Cantuta-Inn.h18669467.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/6baeef5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/0a4c6df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/e770d74d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34100000/34090700/34090623/1f81d6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Van Gogh Room in Villa

[](https://www.expedia.ca/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information)

Purcellville

9.0/10

Wonderful

(67)

"Wonderful "

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

Joseph S.

CA $414

CA $536 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Purcellville-Hotels-The-Van-Gogh-Room-In-Villa.h34090623.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/4b302580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/78704f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/e0f66792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34330000/34329600/34329573/957e6eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn\~pasture-pool view

[](https://www.expedia.ca/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information)

Purcellville

9.8/10

Exceptional

(36)

"Beautiful location, quiet, and Maud is a wonderful person."

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

Dennis G.

CA $483

CA $660 total

includes taxes & fees

Dec 12 - Dec 13

[](https://www.expedia.ca/Purcellville-Hotels-Monet-HoneymoonSuite-Elegant-Lrg-2rm-Wbalcony-In-VillaMountnpasture-Pool-View.h34329573.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/1efbf58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/7243fdc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/6148332c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/64000000/63860000/63853900/63853807/9e11ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

[](https://www.expedia.ca/Lovettsville-Hotels-Stone-Manor-Boutique-Inn-Country-Manor-With-Breathtaking-Gardens-And-Event.h63853807.Hotel-Information)

Lovettsville

10/10

Exceptional

(1)

"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."

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

Lukas D.

CA $2,434

CA $3,283 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Lovettsville-Hotels-Stone-Manor-Boutique-Inn-Country-Manor-With-Breathtaking-Gardens-And-Event.h63853807.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/20bc954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/03c5456b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/f59e70a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186918/76ebda88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information)

Berkeley Springs

10/10

Exceptional

(3)

"Beautiful house. Renovations are not quite complete yet, and the electronic locks needed extra communication with the owner to use, but still a great stay. Perfect location and this place will be gorgeous after renovations are complete."

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

Daniel F.

CA $268

CA $390 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Bird-Nest-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186918.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/eaa4b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/9aa4d92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (The Bamford Suite)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/50b1e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f8c19c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hillbrook Inn

[](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information)

Charles Town

8.6/10

Excellent

(671)

"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"

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

Nataliya

CA $210

CA $270 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/c77e2458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/af61e3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/348df720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186922/e5fc9b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information)

Berkeley Springs

10/10

Exceptional

(3)

"My partner and I have both stayed in some pretty high end hotels and we were so impressed!! By far the best VRBO i’ve stayed in-newly renovated and decorated. You don’t want to pass up this hidden gem convenient to everything in Berkeley Springs!"

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

Deirdre A.

CA $268

CA $390 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186922.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/964cfe73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/9485d69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/d69939f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video library](https://images.trvl-media.com/lodging/109000000/108020000/108011600/108011538/ac634e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 50's Drive-In Inside the Grand Castalian Inn B&B

[](https://www.expedia.ca/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information)

Berkeley Springs

CA $300

CA $430 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Berkeley-Springs-Hotels-50s-Drive-In-Inside-The-Grand-Castalian-Inn-BB.h108011538.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/2778d99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/a606ba47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/7a0299f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107190000/107187000/107186920/ad0ecad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Appalachian Suite In Town!- The Grand Castalian Inn B&B

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information)

Berkeley Springs

10/10

Exceptional

(2)

"We loved the spot and will be back!"

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

Seth W.

CA $284

CA $411 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Berkeley-Springs-Hotels-Appalachian-Suite-In-Town-Inside-Newly-Remodeled-Victorian-Home.h107186920.Hotel-Information)

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26&regionId=6056879&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in

](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)

## 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 B&B information

| Number of reviews | 1,140     |
| ----------------- | --------- |
| Accommodation     | 34 B&B    |
| Lowest Price      | CA $196   |
| Highest Price     | CA $3,283 |

## Frequently asked questions

### What is the nightly rate for a B&B in Winchester?

### When is the best time to book a B&B in Winchester?

> April, in particular, is a popular choice for visitors, as it offers a wonderful blend of comfortable weather and lively local festivals, such as the Winchester Science Festival. The mild climate encourages outdoor strolls through the picturesque gardens and along the River Itchen, superb for those who appreciate a blend of culture and nature.
> 
>   
> For those seeking a more budget-friendly option, consider visiting in November. This month allows for a quieter experience, where you can enjoy the charm of Winchester's historic streets adorned for the festive season. It's an ideal time for leisurely exploration, with the city's attractions less crowded and often offering special events and markets.

### What is the difference between a Winchester B&B and a hotel?

## Explore a world of travel with Expedia

- Lodging
- Flights
- Packages
- More ways to book

- [3 Star Hotels in Old Town Winchester ](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels)
- [4 Star Hotels in Stephens City ](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels)
- [Hotels near Apple Blossom Mall ](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Berryville ](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Berryville ](https://www.expedia.ca/Berryville-Hotels-Luxury-Hotel.0-0-d184082-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Berryville Hotels ](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels)
- [Inns in Berryville ](https://www.expedia.ca/Berryville-Inns.d184082-aaInns.Travel-Guide-Accommodation)
- [Apartments in Boyce ](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation)
- [B&B in Boyce ](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Boutique Hotels in Boyce ](https://www.expedia.ca/Boyce-Hotels-Boutique-Hotel.0-0-d184084-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Boyce Hotels ](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels)
- [Motels in Boyce ](https://www.expedia.ca/Boyce-Motels.d184084-aaMotels.Travel-Guide-Accommodation)
- [Hotels near Bright Box Theater ](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels)
- [Motels in Brucetown ](https://www.expedia.ca/Brucetown-Motels.d3000355042-aaMotels.Travel-Guide-Accommodation)
- [Cheap Hotels in Clear Brook ](https://www.expedia.ca/Clear-Brook-Hotels-Cheap-Hotels.0-0-d553248635975870250-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Clear Brook Hotels ](https://www.expedia.ca/Clear-Brook-Hotels.d553248635975870250.Travel-Guide-Hotels)
- [B&B in College Park ](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Vacation Homes in College Park ](https://www.expedia.ca/College-Park-Private-Vacation-Homes.d553248635975870482-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Hotels near Dinosaur Land ](https://www.expedia.ca/Dinosaur-Land-Hotels.0-l553248621532661835-0.Travel-Guide-Filter-Hotels)
- [B&B in Frederick County ](https://www.expedia.ca/Frederick-County-Bed-And-Breakfast.d553248635976431672-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Frederick County ](https://www.expedia.ca/Frederick-County-Cottages.d553248635976431672-aaCottages.Travel-Guide-Accommodation)
- [Gainesboro Hotels ](https://www.expedia.ca/Gainesboro-Hotels.d553248635976006643.Travel-Guide-Hotels)
- [Hotels near George Washington's Office ](https://www.expedia.ca/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels)
- [Farmstay in Gore ](https://www.expedia.ca/Gore-Agritourism.d3000460015-aaAgritourism.Travel-Guide-Accommodation)
- [B&B in Gore ](https://www.expedia.ca/Gore-Bed-And-Breakfast.d3000460015-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Gore ](https://www.expedia.ca/Gore-Chalets.d3000460015-aaChalets.Travel-Guide-Accommodation)
- [Guest Houses in Gore ](https://www.expedia.ca/Gore-Guest-Houses.d3000460015-aaGuestHouses.Travel-Guide-Accommodation)
- [Cheap Hotels in Gore ](https://www.expedia.ca/Gore-Hotels-Cheap-Hotels.0-0-d3000460015-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Gore ](https://www.expedia.ca/Gore-Hotels-Luxury-Hotel.0-0-d3000460015-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Gore Hotels ](https://www.expedia.ca/Gore-Hotels.d3000460015.Travel-Guide-Hotels)
- [Inns in Gore ](https://www.expedia.ca/Gore-Inns.d3000460015-aaInns.Travel-Guide-Accommodation)
- [Lodges in Gore ](https://www.expedia.ca/Gore-Lodges.d3000460015-aaLodges.Travel-Guide-Accommodation)
- [B&B in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Bed-And-Breakfast.d553248635975872368-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cottages in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Cottages.d553248635975872368-aaCottages.Travel-Guide-Accommodation)
- [Villas in Jordan Springs ](https://www.expedia.ca/Jordan-Springs-Villas.d553248635975872368-aaVillas.Travel-Guide-Accommodation)
- [Luxury Hotels in Kernstown ](https://www.expedia.ca/Kernstown-Hotels-Luxury-Hotel.0-0-d553248635975850140-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Kernstown Hotels ](https://www.expedia.ca/Kernstown-Hotels.d553248635975850140.Travel-Guide-Hotels)
- [B&B in Middletown ](https://www.expedia.ca/Middletown-Bed-And-Breakfast.d12013-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Inns in Middletown ](https://www.expedia.ca/Middletown-Inns.d12013-aaInns.Travel-Guide-Accommodation)
- [Motels in Middletown ](https://www.expedia.ca/Middletown-Motels.d12013-aaMotels.Travel-Guide-Accommodation)
- [Apartments in Millwood ](https://www.expedia.ca/Millwood-Apartments.d3000460156-aaApartments.Travel-Guide-Accommodation)
- [B&B in Millwood ](https://www.expedia.ca/Millwood-Bed-And-Breakfast.d3000460156-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Millwood ](https://www.expedia.ca/Millwood-Guest-Houses.d3000460156-aaGuestHouses.Travel-Guide-Accommodation)
- [Millwood Hotels ](https://www.expedia.ca/Millwood-Hotels.d3000460156.Travel-Guide-Hotels)
- [Lodges in Millwood ](https://www.expedia.ca/Millwood-Lodges.d3000460156-aaLodges.Travel-Guide-Accommodation)
- [Townhomes in Millwood ](https://www.expedia.ca/Millwood-Townhomes.d3000460156-aaTownhomes.Travel-Guide-Accommodation)
- [Villas in Millwood ](https://www.expedia.ca/Millwood-Villas.d3000460156-aaVillas.Travel-Guide-Accommodation)
- [Hotels near Mt Hebron Cemetery ](https://www.expedia.ca/Mt-Hebron-Cemetery-Hotels.0-l553248621532661845-0.Travel-Guide-Filter-Hotels)
- [Boutique Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
- [Cheap Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Cheap-Hotels.0-n6164092-0-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Balconies in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Balconies.0-n6164092-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels)
- [Hotels with Free Breakfast in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Breakfast.0-n6164092-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels)
- [Hotels with Free Parking in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Parking.0-n6164092-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels)
- [Hotels with smoking rooms in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Smoking-Rooms.0-n6164092-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Luxury-Hotel.0-n6164092-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Pet-Friendly-Hotel.0-n6164092-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Spa Hotels in Old Town Winchester ](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels)
- [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)
- [Hotels & Resorts for Couples in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)
- [Historic Hotels in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels)
- [Pet-Friendly Hotels in Stephens City ](https://www.expedia.ca/Stephens-City-Hotels-Pet-Friendly-Hotel.0-0-d12076-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [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)
- [Pet-Friendly Hotels in Winchester Historic District ](https://www.expedia.ca/Winchester-Historic-District-Winchester-Hotels-Pet-Friendly-Hotel.0-n918789051029594112-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [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)
- [Flights from Baltimore (BWI) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester)
- [Flights from Denver (DEN) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester)
- [Flights from Dallas (DFW) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester)
- [Flights from El Paso (ELP) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester)
- [Flights from Fort Lauderdale (FLL) to Winchester (WGO) ](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester)
- [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 B&B in Winchester on Expedia.com ](https://www.expedia.com/Winchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation)