20 Best B&B in Winchester, TN - Bed and Breakfast from $191

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

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Our top choices for Winchester bed & breakfast

A spacious living room with a high ceiling, a staircase, and a fireplace.

1. Cozy king ensuite room in historic railroad inn

Cowan

Jeff

$204 nightly

Sep 30 - Oct 1

Total with taxes and fees

A bedroom with a bed, a TV mounted on the wall, a dresser, a chair, and a window with blinds.

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

Cowan

$167 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Cowan

$177 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

Cowan

Brenda L.

$204 nightly

Sep 30 - Oct 1

Total with taxes and fees

A two-story house with a front porch, stone steps, and two lion statues.

5. Tolley House

Lynchburg

charmain

$200 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

6. Nostalgic Q ensuite room in historic railroad inn.

Cowan

Bennett R.

$182 nightly

Sep 30 - Oct 1

Total with taxes and fees

A residential area with houses, a clear sky, and a road.

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

Cowan

$176 nightly

Sep 30 - Oct 1

Total with taxes and fees

A two-story house with a gabled roof, surrounded by a well-maintained garden with lavender plants.

8. Mulberry Lavender Farm and B&B

Mulberry

Karen

$270 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Winchester Hotel Reviews

The Smokehouse Lodge and Cabins

10/10 Excellent

"Great!"

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

10/10 Excellent

". The house was amazing. It was clean, big and comfortable. the view from all of the balcony's was great. We had a problem with one of the AC units. We contacted the host and he had someone there the same day. We enjoyed our stay at the lake; The house was very well stocked. the kayaks were very nice, and everything was there that was needed to use them. We will stay here again if we return to the area. The host could not have been any more helpful than he was. Thank you for allowing us to stay in your house. The Sibling gang."

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

10/10 Excellent

"We had a wonderful Labor Day Weekend at this property with three generations of the family. The house is clean, comfortable, and exactly as described, with a well-stocked kitchen and a fun game room. The dock is a short drive away and very easy to park next to on the side of the road. We came mostly to fish, and would love to come back and try again when it’s not so hot. Doesn’t hurt to bring some shade with you for the morning/midday, but we had a nice time swimming, kayaking, and fishing. The hosts were very communicative and eager to make sure we had a great stay. Would definitely come back."

Find out more about Winchester

Winchester B&B information

Number of reviews	126
Accommodation	5 B&B
Lowest Price	$191
Highest Price	$302

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 $191 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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Upfront pricing

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. Cozy king ensuite room in historic railroad inn

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

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