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

Bed and Breakfast in Winchester

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 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, (180 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
The price is NZ$310
includes taxes & fees
11 Oct - 12 Oct
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 NZ$302
includes taxes & fees
18 Oct - 19 Oct
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, (359 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 NZ$277
includes taxes & fees
6 Oct - 7 Oct
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 NZ$586
includes taxes & fees
4 Oct - 5 Oct
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 NZ$521
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.

6. 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 NZ$580
includes taxes & fees
18 Oct - 19 Oct
Chesterfield Inn
A two-story building with a white facade and green shutters, a covered front porch, and a sign for the "M" Inn.

7. 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 NZ$264
includes taxes & fees
1 Nov - 2 Nov
Monadnock Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

8. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (58 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is NZ$282
includes taxes & fees
1 Nov - 2 Nov
Four Columns Inn
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 NZ$607
includes taxes & fees
8 Oct - 9 Oct
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

10. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (40 reviews)
"Terry and Paul are wonderful warm Innkeepers. The inn is classically New England charming. The lake view is stunning. Appreciated the little touches like nighty cookies, water and snacks in the room."
United States
Jeffrey
The price is NZ$582
includes taxes & fees
21 Oct - 22 Oct
The Maguire House Bed & Breakfast
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Very nice staff and enjoyed my stay."
Charlene 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Winchester

Winchester B&B information

Number of reviews
1,292
Accommodation
13 B&B
Lowest Price
NZ$264
Highest Price
NZ$607

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 well-liked B&Bs in the area: Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of Winchester. Enjoy the free full breakfast and private garden. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the city centre. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the city centre. 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 New England Sweetwater Farm & Distillery on your list if you want to see more of the area.

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