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Check prices for these dates

Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May
In one month
15 May - 17 May
In two months
12 June - 14 June

Our top choices for Winchester bed & breakfast

Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AU$204
includes taxes & fees
15 Apr - 16 Apr
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, (28 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is AU$196
includes taxes & fees
15 Apr - 16 Apr
Four Columns Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (351 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AU$227
includes taxes & fees
26 Apr - 27 Apr
Colonel Williams Inn
Terrace/patio

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$361
includes taxes & fees
13 May - 14 May
The Maguire House Bed & Breakfast
Front of property

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 AU$380
includes taxes & fees
18 Apr - 19 Apr
The One Cat B&B
Free daily full 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 AU$243
includes taxes & fees
11 May - 12 May
Centennial House
Exterior

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 AU$387
includes taxes & fees
15 Apr - 16 Apr
Inn on Putney Road
Exterior

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 AU$209
includes taxes & fees
28 Apr - 29 Apr
Monadnock Inn
Front of property – evening/night

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 AU$460
includes taxes & fees
19 Apr - 20 Apr
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$482
includes taxes & fees
22 Apr - 23 Apr
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"Awesome and clean and quiet love the staff"
Jeremiah 2-night trip
Posted 2 hours ago
Colonial Motel And Spa

Find out more about Winchester

Winchester B&B information

Number of reviews
825
Accommodation
13 B&B
Lowest Price
AU$196
Highest Price
AU$482

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, 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 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: Colonel Williams Inn: 9 rooms. 18.2 mi (29.3 km) from the city centre. 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. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the city centre. Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique decor.
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, Rhododendron State Park and Cass Pond are some notable spots. You should put New England Sweetwater Farm & Distillery and Winchester Speedpark on your list if you want to see more of the area.

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