A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check prices for these dates

Next weekend
24 July - 26 July
In two weeks
31 July - 2 Aug
In one month
14 Aug - 16 Aug
In two months
11 Sept - 13 Sept

Our top choices for Winchester bed & breakfast

Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is AU$237
includes taxes & fees
3 Aug - 4 Aug
Colonel Williams Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AU$237
includes taxes & fees
22 July - 23 July
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (47 reviews)
"Can’t go wrong with this place."
United States
John
The price is AU$313
includes taxes & fees
20 July - 21 July
Four Columns Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is AU$358
includes taxes & fees
3 Aug - 4 Aug
The One Cat B&B
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (288 reviews)
"The Inn was charming with lots of character. You can see the pieces of history inside the rooms even though they’ve modernized it for comfort. It was perfect. Stay for us inconvenient locations to the places we needed to go. I would definitely stay there again."
United States
Nicole
The price is AU$256
includes taxes & fees
27 July - 28 July
Monadnock Inn
Terrace/patio

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (38 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$371
includes taxes & fees
13 Aug - 14 Aug
The Maguire House Bed & Breakfast
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (59 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is AU$464
includes taxes & fees
26 July - 27 July
Inn on Putney Road
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (106 reviews)
"Great stay"
United States
Wayne
The price is AU$468
includes taxes & fees
22 July - 23 July
Chesterfield Inn
Outdoor dining

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$486
includes taxes & fees
26 July - 27 July
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great place to stay."
Thomas 1-night trip
Posted 21 hours ago
Latchis Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,150
Accommodation
12 B&B
Lowest Price
AU$237
Highest Price
AU$486

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, Loring Field and Richmond Wildlife Manangement Area 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. 17.2 mi (27.6 km) from the city centre. Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the city centre.
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, Loring Field and Birch Point are some notable spots. You should put Winchester Speedpark and New England Sweetwater Farm & Distillery on your list if you want to see more of the area.

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