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

Find a Bed and Breakfast in Winchester from CA $268

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

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, (15 reviews)
"Beautiful spot!"
United States
Bennett R.
The price is CA $227
CA $296 total
includes taxes & fees
Oct 26 - Oct 27
Nostalgic Q ensuite room in historic railroad inn.
A hallway with a rustic brick wall, a brown leather sofa, a woven rug, and a colorful abstract painting.

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

Eclectic Boutique RR hotel, 2nd flr Q ensuite
Cowan
The price is CA $218
CA $284 total
includes taxes & fees
Oct 26 - Oct 27
Eclectic Boutique RR hotel, 2nd flr Q ensuite
A spacious living room with a large rug, a wooden barrel, and a chandelier.

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

Children’s Choice- Full Bd, Twin Bunks, Family Rm
Cowan
The price is CA $219
CA $285 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is CA $257
CA $334 total
includes taxes & fees
Oct 26 - Oct 27
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
The price is CA $306
CA $353 total
includes taxes & fees
Oct 31 - Nov 1
Tolley House
A spacious living room with a high ceiling, a staircase, and a fireplace.

6. Cozy king ensuite room in historic railroad inn

Cozy king ensuite room in historic railroad inn
Cowan
9.4 out of 10, Exceptional, (16 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
The price is CA $257
CA $334 total
includes taxes & fees
Oct 26 - Oct 27
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.

7. 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.
The price is CA $272
CA $354 total
includes taxes & fees
Oct 29 - Oct 30
Artsy pet-friendly king room/historic railroad inn
A spacious living area with a white sofa, a coffee table, and a large abstract painting on the wall.

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

Retro Vibe RR inn/town! 2nd flr full ensuite BR
Cowan
The price is CA $205
CA $268 total
includes taxes & fees
Oct 26 - Oct 27
Retro Vibe RR inn/town! 2nd flr full ensuite BR
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
The price is CA $246
CA $422 total
includes taxes & fees
Nov 2 - Nov 3
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

Quality Inn Monteagle

Quality Inn Monteagle

8/10 Good
"The staff, rooms, breakfast, etc were fine but there is NO ELEVATOR so be sure to request a room on the first floor is you have a lot of luggage."
Edmund 1-night trip
Posted 4 days ago
Quality Inn Monteagle

Find out more about Winchester

Winchester B&B information

Number of reviews
114
Accommodation
11 B&B
Lowest Price
CA $268
Highest Price
CA $422

Frequently asked questions

Searching for B&Bs in Winchester?
If you're looking for something a little quirkier than your standard hotel, a stay at a bed and breakfast might be the perfect option for your getaway. If your ideal vacation to Winchester includes spending lots of time outside, Harvey's Garden is a good spot to enjoy the scenery.
Are you thinking about a B&B instead of a traditional hotel?
With attentive service, opportunities to interact with the owner, and delectable breakfasts, B&Bs offer a truly one-of-a-kind environment.
What are the top B&Bs in Winchester?
Below is a B&B in the area: Tolley House: 4 rooms. 16.4 mi (26.4 km) from the heart of Winchester. Enjoy the unique décor and patio area.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a stay in 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 74°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Winchester is 64 inches.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Tims Ford and Tims Ford Lake are some notable spots. You might put Twin Creeks Marina and Tim's Ford Marina on your list if you want to see more of the area.
How can I get to and around Winchester?
Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Chattanooga Metropolitan Airport (CHA), which is located 52.8 mi (85 km) from the city center. You can also search for flights into Huntsville International Airport (HSV), which is 52.8 mi (85 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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