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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sep - 21 Sep

B&B in Winchester

Loudoun Valley Manor
Reception

Loudoun Valley Manor

3.0 star property
9.6 out of 10, Exceptional, (254)
"Loved this place so much I came back with my family. Absolutely recommend for anyone on the road or looking to make a nice little trip to the Virginia countryside. "
The price is AED 507
AED 578 total
includes taxes & fees
23 Jul - 24 Jul
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"
The price is AED 699
AED 797 total
includes taxes & fees
30 Jul - 31 Jul
Inn at Evergreen
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!"
The price is AED 694
AED 870 total
includes taxes & fees
22 Jul - 23 Jul
Hillbrook Inn
The Carriage Inn B&B
Courtyard

The Carriage Inn B&B

3.5 star property
9.6 out of 10, Exceptional, (423)
"Excellent, historic, amazing breakfast and hostess"
The price is AED 520
AED 587 total
includes taxes & fees
14 Aug - 15 Aug
The Carriage Inn B&B
Stone Manor Boutique Inn
Garden

Stone Manor Boutique Inn

3.5 star property
9.6 out of 10, Exceptional, (92)
"It is a quiet and elegant property inside The breakfast was delicious and the owners were friendly and hospitable."
The price is AED 798
AED 910 total
includes taxes & fees
27 Jul - 28 Jul
Stone Manor Boutique Inn
Glen Gordon Manor
Exterior

Glen Gordon Manor

3.5 star property
9.8 out of 10, Exceptional, (89)
"The location is good."
The price is AED 915
AED 1,000 total
includes taxes & fees
29 Jul - 30 Jul
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, (68)
"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
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
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
Rustic Log cabin bed and breakfast in Virginia wine country
Interior

Rustic Log cabin bed and breakfast in Virginia wine country

8.0 out of 10, Very Good, (1)
"A very lovely setting in the woods and beautiful houses throughout the neighborhood. Very peaceful location and unique home."
Rustic Log cabin bed and breakfast in Virginia wine country
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
9.8 out of 10, Exceptional, (30)
"Great place. Good food, great beer."
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, (32)
"It is an amazing place with a gorgeous view of the mountains and welcoming host"
The price is AED 1,194
AED 1,654 total
includes taxes & fees
22 Jul - 23 Jul
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view
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
The Van Gogh Room in Villa
Pool

The Van Gogh Room in Villa

9.0 out of 10, Wonderful, (62)
"Good stay. Beautiful view. Having never been to Purceville, I was taken aback by the fact that the establishment on s dirt road. "
The price is AED 1,010
AED 1,319 total
includes taxes & fees
22 Jul - 23 Jul
The Van Gogh Room in Villa
Cantuta Inn
Garden

Cantuta Inn

3.0 star property
9.0 out of 10, Wonderful, (71)
"The proprietor was friendly, gracious, and very knowledgeable about the area. Lovely breakfast. "
Cantuta Inn
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! "
The price is AED 1,319
AED 1,421 total
includes taxes & fees
23 Jul - 24 Jul
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!"
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
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
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

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"Bed was comfortable. Had reasonable breakfast. Able to walk to restaurants and grocery store in same parking lot. "
Barbara 6-night trip
Posted 1 day ago
Comfort Inn & Suites

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many types of vacationers. If your ideal vacation to Winchester includes spending lots of time outside, Jim Barnett Park and Star Fort Civil War Battlefield are good spots to enjoy the scenery.
Why consider a B&B over a traditional hotel room?
Every B&B has its own unique feel. Whether it's a picturesque garden or a sunlit breakfast nook, the small details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Here is a B&B that guests like in the surrounding area: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the downtown core. Enjoy the free full breakfast and fitness center.
When is the best time to stay at a B&B in Winchester?
When you're planning your escape to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What is there to do in Winchester?
Travelers who want to experience Winchester should check out its interesting historical sites and major shopping area. When you want to spend some time in the great outdoors, Jim Barnett Park and Star Fort Civil War Battlefield are some notable spots. You might put Bright Box Theater and Shenandoah Valley Discovery Museum on your list if you want to see more of the area.
How can I get to and around Winchester?
You can map out your trip in and around Winchester ahead of time with these transportation options. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. You can also search for flights into Washington Dulles Intl. Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.