A calm lake with autumn foliage, a dock, and houses along the shore.

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Check prices for these dates

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

Our top choices for Winchester bed & breakfast

A room with two large paintings on the wall, a vase with dried flowers, and a glass table with clear glassware.

1. Nostalgic Q ensuite room in historic railroad inn.

Nostalgic Q ensuite room in historic railroad inn.
Cowan
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful spot!"
United States
Bennett R.
$166 nightly
The price is $190
Sep 23 - Sep 24
Total with taxes and fees
Nostalgic Q ensuite room in historic railroad inn.
A spacious living room with a grand piano, a staircase, and a modern interior design.

2. Retro Vibe RR inn/town! 2nd flr full ensuite BR

Retro Vibe RR inn/town! 2nd flr full ensuite BR
Cowan
$168 nightly
The price is $192
Sep 23 - Sep 24
Total with taxes and fees
Retro Vibe RR inn/town! 2nd flr full ensuite BR
A hallway with a brick wall, a white door leading to a kitchen, and a red wall with a wooden staircase.

3. Children’s Choice- Full Bd, Twin Bunks, Family Rm

Children’s Choice- Full Bd, Twin Bunks, Family Rm
Cowan
$180 nightly
The price is $206
Sep 23 - Sep 24
Total with taxes and fees
Children’s Choice- Full Bd, Twin Bunks, Family Rm
A spacious living room with a large dog lying on the floor, surrounded by various seating options and a fireplace.

4. Artsy pet-friendly Q room in historic railroad inn

Artsy pet-friendly Q room in historic railroad inn
Cowan
9.4 out of 10, Exceptional, (6 reviews)
"Nice, clean room. Had everything we needed. Rachel was very helpful and friendly!"
United States
Brenda L.
$208 nightly
The price is $238
Sep 23 - Sep 24
Total with taxes and fees
Artsy pet-friendly Q room in historic railroad inn
A two-story house with a front porch, stone steps, and two lion statues.

5. Tolley House

Tolley House
3.0 star property
Lynchburg
9.8 out of 10, Exceptional, (46 reviews)
"Friendly hosts, wonderful location"
United Kingdom
charmain
$204 nightly
The price is $236
Oct 2 - Oct 3
Total with taxes and fees
Tolley House
A bedroom with a bed, a desk, a chair, a radiator, a chandelier, a window, and a painting.

6. Eclectic Boutique RR hotel, 2nd flr Q ensuite

Eclectic Boutique RR hotel, 2nd flr Q ensuite
Cowan
$179 nightly
The price is $205
Sep 23 - Sep 24
Total with taxes and fees
Eclectic Boutique RR hotel, 2nd flr Q ensuite
A spacious living room with a high ceiling, a staircase, and a fireplace.

7. Cozy king ensuite room in historic railroad inn

Cozy king ensuite room in historic railroad inn
Cowan
9.4 out of 10, Exceptional, (13 reviews)
"The Inn is a delightful place to originate daily excursions in the area. We were there for an event at Sewanee and it is in an ideal location for access to the University and also the adjacent communities."
United States
Jeff
$186 nightly
The price is $214
Sep 23 - Sep 24
Total with taxes and fees
Cozy king ensuite room in historic railroad inn
A spacious living room with a fireplace, a dining area with a table and chairs, a staircase leading to an upper level, and a view of the outside through large windows.

8. Artsy pet-friendly king room/historic railroad inn

Artsy pet-friendly king room/historic railroad inn
Cowan
9.4 out of 10, Exceptional, (10 reviews)
"Pretty Inn with lots of character and charm."
United States
Jennifer C.
$219 nightly
The price is $252
Sep 23 - Sep 24
Total with taxes and fees
Artsy pet-friendly king room/historic railroad inn
A two-story house with a gabled roof, surrounded by a well-maintained garden with lavender plants.

9. Mulberry Lavender Farm and B&B

Mulberry Lavender Farm and B&B
3.0 star property
Mulberry
9.6 out of 10, Exceptional, (37 reviews)
"An amazing stay So calm and quiet. Loved the animals and breakfast was delicious."
United States
Karen
$268 nightly
The price is $299
Sep 27 - Sep 28
Total with taxes and fees
Mulberry Lavender Farm and 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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Everything was great. Location to the Caverns and other adventures was awesome!"
Misty 2-night trip
Posted 7 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester B&B information

Number of reviews
126
Accommodation
5 B&B
Lowest Price
$190
Highest Price
$299

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $190 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 most popular time to book a B&B in Winchester is during the peak season from May to July, when the area comes alive with vibrant activities and scenic beauty. This period attracts travelers seeking to enjoy the lush landscapes and warm weather, ideal for outdoor exploration and sightseeing. With temperatures ranging from the mid-50s to the low 80s Fahrenheit, visitors can comfortably partake in various activities, such as hiking the picturesque trails or exploring local wineries.

Among these months, July stands out as the height of summer fun, offering a lively atmosphere filled with festivals, farmers' markets, and community events. It's a great time for those who appreciate a bustling environment and the chance to mingle with fellow visitors while soaking up the sun.

For travelers looking for a more budget-friendly experience, consider visiting in November. This month, while quieter, offers a unique charm as the fall foliage begins to fade, providing a peaceful backdrop for leisurely strolls through Winchester's historic downtown or along the scenic Shenandoah River.
What is the difference between a Winchester Bed and 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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