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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Featured B&B in Winchester

Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AU$212
includes taxes & fees
29 Dec - 30 Dec
The Carriage Barn Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AU$243
includes taxes & fees
4 Dec - 5 Dec
Colonel Williams Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Free daily full breakfast
Centennial House

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is AU$309
includes taxes & fees
29 Dec - 30 Dec
Centennial House
Exterior
Inn on Putney Road

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AU$448
includes taxes & fees
1 Dec - 2 Dec
Inn on Putney Road
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"A very quaint property. The room was comfortable and clean."
United States
Frank
The Engel House
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (276)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AU$420
includes taxes & fees
4 Dec - 5 Dec
The One Cat B&B
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AU$499
includes taxes & fees
1 Dec - 2 Dec
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$545
includes taxes & fees
11 Dec - 12 Dec
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. Historic—not for people who want fancy but clean with comfortable beds, very walkable to everything. Loved it!"
Heather 1-night trip
Posted 3 days ago
Latchis Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,021
Accommodation
12 B&B
Lowest Price
AU$212
Highest Price
AU$545

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

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