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Next weekend
Oct 17 - Oct 19
In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7

B&B in Winchester

Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (90)
"The location is good."
$249 nightly
The price is $272
Nov 2 - Nov 3
Total with taxes and fees
Glen Gordon Manor
Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (269)
"We loved this property and will definitely be back! It felt homely, but there were plenty of amenities and also there was plenty of privacy. The breakfasts were tasty and the property was located in the perfect position to visit the wineries! "
$140 nightly
The price is $160
Nov 10 - Nov 11
Total with taxes and fees
Loudoun Valley Manor
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (669)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
$195 nightly
The price is $216
Oct 29 - Oct 30
Total with taxes and fees
Hillbrook Inn
Inn at Evergreen
Free daily full breakfast

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (130)
"This is a lovely property. We were lucky to have a suite - so restful and quiet. The breakfast across the street at the golf club was delicious. There is a lot to do in the area if you're not into golf."
$263 nightly
The price is $300
Nov 1 - Nov 2
Total with taxes and fees
Inn at Evergreen
Stone Manor Boutique Inn
Garden

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (93)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
$242 nightly
The price is $275
Oct 13 - Oct 14
Total with taxes and fees
Stone Manor Boutique Inn
Hopkins Ordinary Bed Breakfast and Ale Works
Family House, Multiple Beds, Balcony, Garden Area | Balcony

Hopkins Ordinary Bed Breakfast and Ale Works

3.0 star property
10.0 out of 10, Exceptional, (31)
"Great place. Good food, great beer."
$323 nightly
The price is $353
Oct 21 - Oct 22
Total with taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (429)
"Excellent accommodations and breakfast. "
$163 nightly
The price is $185
Oct 30 - Oct 31
Total with taxes and fees
The Carriage Inn B&B
Cantuta Inn
Garden

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (73)
"A comfortable, quiet, & beautiful place to stay. Staff was friendly and able to recommend somewhere good for dinner. "
$170 nightly
The price is $190
Oct 13 - Oct 14
Total with taxes and fees
Cantuta Inn
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Exterior

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

2.0 star property
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."
$1,997 nightly
The price is $2,365
Nov 2 - Nov 3
Total with taxes and fees
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
The Inn at Grass Roots Hill
Property entrance

The Inn at Grass Roots Hill

3.0 star property
10.0 out of 10, Exceptional, (2)
"House and property are absolutely beautiful. Staff are amazing and super friendly "
$390 nightly
The price is $445
Nov 12 - Nov 13
Total with taxes and fees
The Inn at Grass Roots Hill
Gay Street Inn
Interior detail

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (34)
"Beautiful historic Inn with incredible owners and service. "
$359 nightly
The price is $387
Oct 15 - Oct 16
Total with taxes and fees
Gay Street Inn
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Dining

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

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!"
$282 nightly
The price is $313
Nov 9 - Nov 10
Total with taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Outdoor pool

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

9.8 out of 10, Exceptional, (36)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
$382 nightly
The price is $435
Oct 13 - Oct 14
Total with taxes and fees
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (65)
"Nice rooms, beautiful property, accommodating host. The pool and gardens are serene and relaxing. Easy drive to many local restaurants, winery’s, breweries…. Close to the AT for those looking to recovery from hiking "
$335 nightly
The price is $381
Oct 13 - Oct 14
Total with taxes and fees
The Van Gogh Room in Villa
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Dining

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

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."
$256 nightly
The price is $284
Nov 2 - Nov 3
Total with taxes and fees
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
Appalachian Suite In Town!- The Grand Castalian Inn B&B
Dining

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

10.0 out of 10, Exceptional, (2)
"We loved the spot and will be back!"
$270 nightly
The price is $299
Nov 2 - Nov 3
Total with taxes and fees
Appalachian Suite In Town!- The Grand Castalian Inn B&B
50's Drive-In Inside the Grand Castalian Inn B&B
Dining

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

2.0 star property
$283 nightly
The price is $314
Nov 2 - Nov 3
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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Parking, staff and shops/restaurants nearby excellent. Not impressed with no tea/coffee in rooms."
Julie 1-night trip
Posted 1 day ago
TRU By Hilton Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
1,105
Accommodation
33 B&B
Lowest Price
$160
Highest Price
$2,365

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 from $160 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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