Photo by Donny Campos

Find Winchester Bed And Breakfast

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

B&B in Winchester

Our top choices for Winchester bed & breakfast

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
The price is ￥20,842
￥22,927 total
includes taxes & fees
Sep 22 - Sep 23
Colonel Williams Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
8.4 out of 10, Very Good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
The price is ￥29,898
￥32,589 total
includes taxes & fees
Aug 31 - Sep 1
Green River Bridge Inn
Four Columns Inn
Romantic Room | 1 bedroom, free WiFi, bed sheets

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (154)
"Excellent phenomenal cleanliness and so polite"
The price is ￥26,044
￥28,258 total
includes taxes & fees
Sep 2 - Sep 3
The Carriage Barn Inn
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (269)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
Monadnock Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (162)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
The price is ￥29,608
￥31,296 total
includes taxes & fees
Sep 15 - Sep 16
Centennial House
The Engel House
Exterior

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
The Engel House
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is ￥41,462
￥45,608 total
includes taxes & fees
Sep 7 - Sep 8
The One Cat B&B
The Maguire House Bed & Breakfast
Property grounds

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is ￥37,259
￥37,259 total
includes taxes & fees
Sep 10 - Sep 11
The Maguire House Bed & Breakfast
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (52)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is ￥43,336
￥47,670 total
includes taxes & fees
Sep 8 - Sep 9
Inn on Putney Road
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is ￥44,277
￥48,041 total
includes taxes & fees
Aug 31 - Sep 1
Chesterfield 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Winchester B&B information

Number of reviews
286
Accommodation
12 B&B
Lowest Price
￥20,842
Highest Price
￥44,277

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be just the right fit for your trip to Winchester. While you're enjoying your trip to Winchester, Richmond Wildlife Manangement Area and Rhododendron State Park are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the best choice for your stay?
Every B&B has its own unique feel. Whether it's a cozy reading space or a beautiful breakfast room, the tiny details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Winchester?
Below are some well-liked B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester.Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the downtown core. Enjoy the deli and patio area. Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Inn on Putney Road: 6 rooms. Located 10.7 mi (17.3 km) from the core of Winchester. Enjoy the free full breakfast and onsite spa services.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Richmond Wildlife Manangement Area and Rhododendron State Park are some notable spots. You might put New England Sweetwater Farm & Distillery and Pisgah State Park on your list if you want to see more of the area.