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Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
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Dec 26 - Dec 28
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Jan 23 - Jan 25

B&B in Winchester

Exterior
Glen Gordon Manor

Glen Gordon Manor

3.5 star property
Huntly
9.8 out of 10, Exceptional, (93)
"Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean."
United States
KYLE
$289 nightly
The price is $316
Dec 2 - Dec 3
Total with taxes and fees
Glen Gordon Manor
Reception
Loudoun Valley Manor

Loudoun Valley Manor

3.0 star property
Waterford
9.6 out of 10, Exceptional, (276)
"Great location for visiting wineries"
United States
Anne
$141 nightly
The price is $161
Dec 21 - Dec 22
Total with taxes and fees
Loudoun Valley Manor
Free daily full breakfast
Inn at Evergreen

Inn at Evergreen

3.5 star property
Haymarket
9.4 out of 10, Exceptional, (131)
"Clean,very nice facility "
United States
Matthew P
$206 nightly
The price is $235
Dec 3 - Dec 4
Total with taxes and fees
Inn at Evergreen
Property amenity
Hillbrook Inn

Hillbrook Inn

4.0 star property
Charles Town
8.6 out of 10, Excellent, (670)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
$195 nightly
The price is $216
Dec 8 - Dec 9
Total with taxes and fees
Hillbrook Inn
Family House, Multiple Beds, Balcony, Garden Area | Balcony
Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
Sperryville
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
United States
Phil
$267 nightly
The price is $292
Dec 1 - Dec 2
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
Garden
Stone Manor Boutique Inn

Stone Manor Boutique Inn

3.5 star property
Lovettsville
9.6 out of 10, Exceptional, (95)
"The experience was very good, will return in the future. The breakfast was excellent. "
United States
Marvin
$213 nightly
The price is $243
Dec 7 - Dec 8
Total with taxes and fees
Stone Manor Boutique Inn
Exterior
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event

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

2.0 star property
Lovettsville
10.0 out of 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
Lukas D.
$2,016 nightly
The price is $2,387
Dec 7 - Dec 8
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Property entrance
The Inn at Grass Roots Hill

The Inn at Grass Roots Hill

3.0 star property
Purcellville
9.8 out of 10, Exceptional, (6)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
United States
Chad
$459 nightly
The price is $523
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Grass Roots Hill
Garden
Cantuta Inn

Cantuta Inn

3.0 star property
Harpers Ferry
9.0 out of 10, Wonderful, (74)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
United States
Aleta
$160 nightly
The price is $179
Dec 14 - Dec 15
Total with taxes and fees
Cantuta Inn
Dining
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B

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

Berkeley Springs
10.0 out of 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
Daniel F.
$256 nightly
The price is $284
Dec 7 - Dec 8
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Interior detail
Gay Street Inn

Gay Street Inn

3.5 star property
Washington
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
United States
Renee
$359 nightly
The price is $387
Dec 4 - Dec 5
Total with taxes and fees
Gay Street Inn
Pool
The Van Gogh Room in Villa

The Van Gogh Room in Villa

Purcellville
9.0 out of 10, Wonderful, (67)
"Wonderful "
United States
Joseph S.
$372 nightly
The price is $424
Dec 1 - Dec 2
Total with taxes and fees
The Van Gogh Room in Villa
Outdoor pool
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

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

Purcellville
9.8 out of 10, Exceptional, (36)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
$423 nightly
The price is $482
Dec 1 - Dec 2
Total with taxes and fees
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Courtyard
The Carriage Inn B&B

The Carriage Inn B&B

3.5 star property
Charles Town
9.6 out of 10, Exceptional, (437)
"Excellent accommodations and breakfast. "
United States
William
$127 nightly
The price is $144
Dec 1 - Dec 2
Total with taxes and fees
The Carriage Inn B&B
Dining
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B

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

Berkeley Springs
10.0 out of 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
Deirdre A.
$256 nightly
The price is $284
Dec 7 - Dec 8
Total with taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining
Appalachian Suite In Town!- The Grand Castalian Inn B&B

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

Berkeley Springs
10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
United States
Seth W.
$270 nightly
The price is $299
Dec 7 - Dec 8
Total with taxes and fees
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Dining
50's Drive-In Inside the Grand Castalian Inn B&B

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

2.0 star property
Berkeley Springs
$283 nightly
The price is $314
Dec 7 - Dec 8
Total with taxes and fees
50's Drive-In Inside the Grand Castalian Inn B&B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"Property had a newness about it. Checkin was cheerful. Room was clean and functional. Definitely in the top 5 of Hampton Inns."
George 1-night trip
Posted 20 hours ago
Hampton Inn Winchester N/Conference Center, VA

Find out more about Winchester

Winchester B&B information

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Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Winchester?
The best time to book a B&B in Winchester is during the vibrant fall months of September and October. This period attracts travelers looking to experience the stunning autumn foliage and partake in various local events, all while enjoying the comfortable temperatures ranging from the mid-50s to low 70s Fahrenheit. The scenery is particularly enchanting as the leaves change, creating a picturesque backdrop for outdoor activities such as hiking the nearby trails or exploring the charming downtown area.

September often sees a delightful mix of warm days and cool evenings, making it ideal for leisurely strolls through local parks or visiting historical sites. The community also hosts several festivals celebrating the harvest, offering visitors a taste of local culture and cuisine.

For those seeking a more budget-friendly experience, consider planning your trip in November. This quieter month provides a unique opportunity to explore Winchester's attractions without the crowds, and you can enjoy the area's natural beauty as the landscape transitions into winter.
What is the difference between a Winchester Bed & Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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