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Our top choices for Winchester bed & breakfast

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (350 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ¥24,121
¥26,533 total
includes taxes & fees
Apr 5 - Apr 6
Colonel Williams Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is ¥20,697
¥22,559 total
includes taxes & fees
Apr 7 - Apr 8
Four Columns Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ¥22,162
¥24,046 total
includes taxes & fees
Apr 20 - Apr 21
The Carriage Barn Inn

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is ¥38,857
¥42,742 total
includes taxes & fees
Apr 18 - Apr 19
The One Cat B&B

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is ¥41,374
¥41,374 total
includes taxes & fees
Apr 23 - Apr 24
The Maguire House Bed & Breakfast

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (174 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is ¥28,632
¥30,264 total
includes taxes & fees
May 3 - May 4
Centennial House

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (280 reviews)
"This is a good representation of staying in an inn of the 1969s. "
United States
Frank
The price is ¥21,728
¥23,574 total
includes taxes & fees
Apr 6 - Apr 7
Monadnock Inn

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is ¥37,426
¥41,169 total
includes taxes & fees
Apr 5 - Apr 6
Inn on Putney Road

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is ¥47,761
¥51,821 total
includes taxes & fees
Apr 19 - Apr 20
Chesterfield Inn

Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
The price is ¥43,615
¥54,533 total
includes taxes & fees
Apr 11 - Apr 12
Private bedroom in the Green River Bridge Inn. A full breakfast is 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

Find out more about Winchester

Winchester B&B information

Number of reviews
823
Accommodation
13 B&B
Lowest Price
¥22,559
Highest Price
¥54,533

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, Rhododendron State Park and Loring Field 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 B&Bs in the area: Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the downtown core. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. Green River Bridge Inn: 4 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the deli and patio area. Monadnock Inn: 11 rooms. Located 17.2 mi (27.6 km) from the core of Winchester.
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, Cass Pond and Rhododendron State Park are some notable spots. You might put Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.

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