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Our top choices for Winchester bed & breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is AU$204
includes taxes & fees
14 Jan - 15 Jan
The Carriage Barn Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (342 reviews)
"Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! "
United States
Ekaterina
The price is AU$243
includes taxes & fees
27 Jan - 28 Jan
Colonel Williams Inn

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AU$221
includes taxes & fees
15 Jan - 16 Jan
The One Cat B&B

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is AU$288
includes taxes & fees
1 Feb - 2 Feb
Centennial House

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AU$385
includes taxes & fees
14 Jan - 15 Jan
Inn on Putney Road

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 AU$377
includes taxes & fees
11 Feb - 12 Feb
The Maguire House Bed & Breakfast

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (277 reviews)
"The room was comfortable and clean wwhen we arrived "
United States
Peter
Monadnock Inn

The Engel House

The Engel House
3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17 reviews)
"The perfect Vermont Bed and Breakfast. "
United States
Lee
The Engel House

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is AU$497
includes taxes & fees
18 Jan - 19 Jan
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 AU$521
includes taxes & fees
20 Jan - 21 Jan
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
1,071
Accommodation
13 B&B
Lowest Price
AU$204
Highest Price
AU$521

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cosy environment, a bed and breakfast might be just the right fit for your trip to Winchester. While you're enjoying your trip to Winchester, Barden State Wildlife Management Area and Loring Field are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is a good option for your stay?
Every B&B has its own unique feel — whether it's a comfy common area with a fireplace or a beautiful breakfast room, the little 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: Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the city centre. Enjoy the local cuisine breakfast and library. Inn on Putney Road: 6 rooms. Located 10.7 mi (17.3 km) from the core of Winchester. Enjoy the free full breakfast and on-site spa services.
When should I book my B&B in Winchester?
When you're dreaming of a trip to Winchester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.
What is there to do in Winchester?
When you want to spend some time in the great outdoors, Cass Pond and Barden State Wildlife Management Area are some notable spots. You should put New England Sweetwater Farm & Distillery and Bennett Gorge on your list if you want to see more of the area.

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