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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

B&B in Winchester

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (256)
"Wonderful, clean, quiet, affordable and friendly lodging option when winery-hopping and/or sightseeing in the area."
$144 nightly
The price is $165
Aug 17 - Aug 18
Total includes taxes and fees
Loudoun Valley Manor
Inn at Evergreen
Free daily full breakfast

Inn at Evergreen

3.5 star property
9.4 out of 10, Exceptional, (127)
"Wonderful place to stay"
$211 nightly
The price is $241
Aug 17 - Aug 18
Total includes 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
Aug 17 - Aug 18
Total includes taxes and fees
Stone Manor Boutique Inn
Hillbrook Inn
Property amenity

Hillbrook Inn

4.0 star property
8.6 out of 10, Excellent, (668)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
$218 nightly
The price is $242
Aug 17 - Aug 18
Total includes taxes and fees
Hillbrook Inn
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
$249 nightly
The price is $272
Aug 19 - Aug 20
Total includes taxes and fees
Glen Gordon Manor
Lily Garden Bed and Breakfast
Front of property

Lily Garden Bed and Breakfast

2.5 star property
9.6 out of 10, Exceptional, (71)
"The facility is quite small, even for 2 adults. There were ants on the counters. The provided breakfast was wonderful and plentiful. Nicely decorated. "
Lily Garden Bed and Breakfast
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (424)
"Excellent, historic, amazing breakfast and hostess"
$168 nightly
The price is $190
Aug 21 - Aug 22
Total includes taxes and fees
The Carriage Inn B&B
Cantuta Inn
Garden

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (71)
"Clean and well taken care of. Owner was friendly and cooked a nice breakfast. A quick walk to the downtown of Harper's Ferry."
Cantuta Inn
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (63)
"Good stay. Beautiful view. Having never been to Purceville, I was taken aback by the fact that the establishment on s dirt road. "
$343 nightly
The price is $391
Aug 15 - Aug 16
Total includes taxes and fees
The Van Gogh Room in Villa
Mayneview B&B
Outdoor spa tub

Mayneview B&B

4.0 star property
8.2 out of 10, Very Good, (413)
"Fabulous place to stay, beautiful and clean, delicious breakfast, easy access to Shenandoah National Park, close to the little downtown area. "
Mayneview B&B
Maria's Garden and Inn
Porch

Maria's Garden and Inn

3.0 star property
9.4 out of 10, Exceptional, (125)
"Wonderful stay wonderful hosts great breakfast!"
Maria's Garden and 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."
$311 nightly
The price is $340
Sep 1 - Sep 2
Total includes taxes and fees
Hopkins Ordinary Bed Breakfast and Ale Works
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, (34)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
$395 nightly
The price is $450
Aug 15 - Aug 16
Total includes taxes and fees
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
Caravan Suite location Private Lily Garden BnB
Property grounds

Caravan Suite location Private Lily Garden BnB

10.0 out of 10, Exceptional, (58)
"I recommend this place 100 percent"
Caravan Suite location Private Lily Garden BnB
Inn of the Shenandoah
Front of property

Inn of the Shenandoah

4.0 star property
9.8 out of 10, Exceptional, (40)
"It was an awesome place to stay!!"
Inn of the Shenandoah
The Manor at Courtland Farm
Outdoor pool

The Manor at Courtland Farm

3.5 star property
9.2 out of 10, Wonderful, (47)
"This was one of the most beautiful places I have ever stayed. The service was excellent!"
The Manor at Courtland Farm
Gay Street Inn
Interior detail

Gay Street Inn

3.5 star property
10.0 out of 10, Exceptional, (33)
"Great place to stay in Washington VA to walk to inn at little Washington, patty O's (6 min walk), bakery, chocolates and rural landscape! "
$359 nightly
The price is $387
Aug 21 - Aug 22
Total includes taxes and fees
Gay Street Inn
South Court Inn
Front of property

South Court Inn

4.0 star property
10.0 out of 10, Exceptional, (8)
"The family running the inn is a wonderful and young couple preserving the history of the house and creating inclusive and welcoming environment for the guests. "
South Court 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!"
$295 nightly
The price is $327
Aug 18 - Aug 19
Total includes taxes and fees
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
Historic Hideaway with King Bed & Spa-Inspired Bath
1 bedroom, WiFi, bed sheets

Historic Hideaway with King Bed & Spa-Inspired Bath

$589 nightly
The price is $670
Aug 17 - Aug 18
Total includes taxes and fees
Historic Hideaway with King Bed & Spa-Inspired Bath
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Pet friendly, wonderful breakfast, clean, and great staff."
Connie 1-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Winchester

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 $165 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.