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
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

Our top choices for Winchester bed & breakfast

A two-story house with a red door, green shutters, and a snow-covered front yard.

1. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (177 reviews)
"David was incredibly hospitable. I thoroughly enjoyed my stay. "
United States
Amy
The price is AU$253
includes taxes & fees
13 Sept - 14 Sept
Centennial House
A wooden table set with plates, cutlery, and a folded napkin.

2. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is AU$225
includes taxes & fees
8 Sept - 9 Sept
The Carriage Barn Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

3. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 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$231
includes taxes & fees
8 Sept - 9 Sept
Colonel Williams Inn
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

4. 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$444
includes taxes & fees
8 Sept - 9 Sept
The One Cat B&B
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

5. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is AU$450
includes taxes & fees
8 Sept - 9 Sept
Inn on Putney Road
A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

6. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (292 reviews)
"Very nice, clean, and a good vibe. An older building but very charming. Would certainly stay again."
United States
Jed
The price is AU$254
includes taxes & fees
6 Sept - 7 Sept
Monadnock Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is AU$218
includes taxes & fees
13 Sept - 14 Sept
Four Columns Inn
A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

8. 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$410
includes taxes & fees
10 Sept - 11 Sept
The Maguire House Bed & Breakfast
A table with various food items and a bottle of wine, overlooking a lush garden.

9. 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$472
includes taxes & fees
13 Sept - 14 Sept
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 15 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester B&B information

Number of reviews
1,176
Accommodation
12 B&B
Lowest Price
AU$218
Highest Price
AU$472

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 well-liked B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the heart of Winchester. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the city centre. Enjoy the free full breakfast and unique decor. The Carriage Barn Inn: 4 rooms. Situated 11.8 mi (18.9 km) from the heart of Winchester. 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, Birch Point and Cass Pond are some notable spots. You should put Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.

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