A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Winchester bed & breakfast

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.

1. Glen Gordon Manor

Glen Gordon Manor
3.5 star property
Huntly
9.8 out of 10, Exceptional, (99 reviews)
"Staff was efficient, professional, personable, thoughtful. Facilities were lovely, Breakfast was excellent."
United States
Alexander and Judith
The price is HK$3,130
HK$3,609 total
includes taxes & fees
1 Oct - 2 Oct
Glen Gordon Manor
A two-story house with a front porch, American flags, and a mailbox.

2. The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (457 reviews)
"Amazing place with incredible history!"
United States
Andrea
The price is HK$1,322
HK$1,493 total
includes taxes & fees
28 Sept - 29 Sept
The Carriage Inn B&B
A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

3. Loudoun Valley Manor

Loudoun Valley Manor
3.0 star property
Waterford
9.6 out of 10, Exceptional, (332 reviews)
"Great location and service. A perfect weekend getaway from DC or Richmond."
United States
Mindi
The price is HK$1,177
HK$1,341 total
includes taxes & fees
28 Sept - 29 Sept
Loudoun Valley Manor
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.

4. Light Horse Inn

Light Horse Inn
2.0 star property
Harpers Ferry
9.4 out of 10, Exceptional, (148 reviews)
"The Inn is old so being a bit dated is fine. I would suggest better entry directions and parking directions. The plated breakfast by LEO was superb, so a special thanks to her. I am atgempting the baked french toast tomorrow morning."
United States
Howard
The price is HK$1,165
HK$1,246 total
includes taxes & fees
6 Oct - 7 Oct
Light Horse Inn
Two people seated at a table with a view of a sunset over a hilly landscape.

5. Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.

Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Purcellville
9.8 out of 10, Exceptional, (39 reviews)
"Beautiful location, quiet, and Maud is a wonderful person."
United States
Dennis G.
The price is HK$3,138
HK$4,060 total
includes taxes & fees
28 Sept - 29 Sept
Monet HoneymoonSuite in villa.Elegant Lrg 2rm w/balcony, jacuzzi n phenom.view.
Two people seated at a table with a view of a sunset over a hilly landscape.

6. The Van Gogh Room in Villa

The Van Gogh Room in Villa
Purcellville
9.0 out of 10, Wonderful, (71 reviews)
"Perfect idyllic retreat -- lovely property, cozy room, AMAZING art and chill vibes. Lovely host, too. Would love to go back :)"
United States
Anonymous traveller
The price is HK$2,549
HK$3,103 total
includes taxes & fees
28 Sept - 29 Sept
The Van Gogh Room in Villa
A hallway with a dark wooden floor, white walls, and a large mirror on the right. There is a door at the end of the hallway and a small table with a vase of flowers on the left.

7. Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (141 reviews)
"A very beautiful experience. The staff was amazing. The country club access was such a treat. The room was breathtaking. We can’t wait to go back:"
United States
Adriane
The price is HK$2,030
HK$2,314 total
includes taxes & fees
29 Sept - 30 Sept
Inn at Evergreen
A cozy seating area with two rocking chairs and a small table, overlooking a lush garden through a large arched window.

8. Gay Street Inn

Gay Street Inn
3.5 star property
Washington
10.0 out of 10, Exceptional, (36 reviews)
"Super cute place! Drew was so helpful and friendly. Loved the breakfast and the whole vibe of the house. Highly recommend,"
United States
Kathryn
The price is HK$2,534
HK$2,732 total
includes taxes & fees
30 Sept - 1 Oct
Gay Street Inn
A two-story house with a porch and a small garden area.

9. Hopkins Ordinary Bed Breakfast and Ale Works

Hopkins Ordinary Bed Breakfast and Ale Works
3.0 star property
Sperryville
9.8 out of 10, Exceptional, (38 reviews)
"Staff was wonderful and caring! Breakfast was delicious. The tavern had wonderful beer and we enjoyed meeting Norman the beagle."
United States
Deborah
The price is HK$2,279
HK$2,628 total
includes taxes & fees
20 Oct - 21 Oct
Hopkins Ordinary Bed Breakfast and Ale Works
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

10. Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
10.0 out of 10, Exceptional, (2 reviews)
"We only spent one night here because my wife had training in the town of Purcellville. However, we were treated like family. Kenny, the general manager, was very kind, welcoming and attentive. He personally prepared our breakfast. Noé, the caretaker was wonderful and always available to us. Beyond that, this is one of the most beautiful, scenic properties I have ever experienced. You have to see it for yourself. Highly recommended!"
United States
Andrew
The price is HK$2,196
HK$2,683 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Lakefront 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

11. 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 reviews)
"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.
The price is HK$1,705
HK$2,330 total
includes taxes & fees
28 Sept - 29 Sept
Bird Nest Suite In Town!- Inside the Grand Castalian Inn B&B
A traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

12. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (691 reviews)
"It was beautiful location. The staff was amazing and the food was excellent highly recommend."
United States
Cecile
The price is HK$1,169
HK$1,505 total
includes taxes & fees
6 Oct - 7 Oct
Hillbrook Inn
A grand staircase with a chandelier, leading to an open doorway with a view of a garden.

13. The Inn at Grass Roots Hill

The Inn at Grass Roots Hill
3.0 star property
Purcellville
9.2 out of 10, Wonderful, (10 reviews)
"Beautiful venue, great service, and very close to the local downtown. Would stay again, highly recommend. "
United States
Robert
The price is HK$4,573
HK$5,214 total
includes taxes & fees
28 Sept - 29 Sept
The Inn at Grass Roots Hill
A large two-story house with a stone exterior, a covered porch, and a well-maintained garden.

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

Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
Lovettsville
10.0 out of 10, Exceptional, (1 review)
"Everyone was so kind, house was beautiful and the food was amazing. Really made us feel like home. Highly recommend."
United States
Lukas D.
The price is HK$90,206
HK$113,596 total
includes taxes & fees
28 Sept - 29 Sept
Stone Manor Boutique Inn - Country Manor with Breathtaking Gardens and Event
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

15. 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 reviews)
"We loved the spot and will be back!"
United States
Seth W.
The price is HK$1,795
HK$2,432 total
includes taxes & fees
1 Oct - 2 Oct
Appalachian Suite In Town!- The Grand Castalian Inn B&B
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

16. 50's Drive-In Inside the Grand Castalian Inn B&B

50's Drive-In Inside the Grand Castalian Inn B&B
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,885
HK$2,534 total
includes taxes & fees
28 Sept - 29 Sept
50's Drive-In Inside the Grand Castalian Inn B&B
A two-story house with a front porch, a central staircase, and a small tower-like structure on the roof.

17. 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, (4 reviews)
"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.
The price is HK$1,795
HK$2,432 total
includes taxes & fees
4 Oct - 5 Oct
River Retreat Suite In Town!- Inside The Grand Castalian Inn B&B
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

18. Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included

Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
The price is HK$2,471
HK$2,996 total
includes taxes & fees
4 Oct - 5 Oct
Lakefront Gateway 1 BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

19. Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included

Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
Purcellville
The price is HK$2,745
HK$3,335 total
includes taxes & fees
4 Oct - 5 Oct
Peaceful Lakefront 1BR 1 Full Bath w/ Private Island Access & Breakfast Included
A building with a staircase leading to a gated entrance, surrounded by a grassy area.

20. Lakefront B&B Room w/Private Island Access + Breakfast Included

Lakefront B&B Room w/Private Island Access + Breakfast Included
Purcellville
The price is HK$3,193
HK$3,890 total
includes taxes & fees
19 Oct - 20 Oct
Lakefront B&B Room w/Private Island Access + Breakfast Included
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

Skyland

Skyland

10/10 Excellent
"Clean and will maintained, close to nature"
Ujjwal 1-night trip
Posted 16 hours ago
Skyland

Find out more about Winchester

Winchester B&B information

Number of reviews
277
Accommodation
48 B&B
Lowest Price
HK$1,246
Highest Price
HK$113,596

Frequently asked questions

Searching for B&Bs in Winchester?
Whether you're on a romantic holiday and want to stay somewhere quiet, or you're travelling solo and looking to chat with locals, B&Bs can be a great choice for many travellers. If your ideal holiday 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 a unique charm — whether it's a cosy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Winchester?
Below are some well-liked B&Bs in the surrounding area: Hillbrook Inn: 9 rooms. 13.5 mi (21.7 km) from the city centre. Enjoy the free full breakfast and fitness centre. The Carriage Inn B&B: 7 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the designer toiletries and in-room fireplace.
What's the best time of year to stay at a B&B in Winchester?
When you're planning your getaway to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What is there to do in Winchester?
Travellers who want to experience Winchester should visit 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 should 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?
Planning your excursions in and around Winchester is easier 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. Otherwise, you can search for flights to Washington Dulles International Airport (IAD), which is 41.7 mi (67.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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