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
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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
9.8 out of 10, Exceptional, (192 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 AED 547
AED 578 total
includes taxes & fees
15 Nov - 16 Nov
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, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
The price is AED 435
AED 472 total
includes taxes & fees
11 Nov - 12 Nov
The Carriage Barn Inn
A large, two-story house with a snow-covered driveway and surrounding trees.

3. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
8 Nov - 9 Nov
Chesterfield Inn
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

4. 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 AED 980
AED 1,078 total
includes taxes & fees
5 Nov - 6 Nov
Inn on Putney Road
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

5. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is AED 541
AED 589 total
includes taxes & fees
8 Nov - 9 Nov
Four Columns Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

6. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (363 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
The price is AED 629
AED 692 total
includes taxes & fees
8 Nov - 9 Nov
Colonel Williams 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, (296 reviews)
"The building and interior was big on ambiance and charm. The staff was very cordial and helpful. I would suggest the addition of an ice machine"
United States
Jim
The price is AED 503
AED 546 total
includes taxes & fees
5 Nov - 6 Nov
Monadnock Inn
A porch with a table set for two, a chair, and a potted plant.

8. 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
2.0 out of 10, (1 review)
The price is AED 1,010
AED 1,230 total
includes taxes & fees
10 Nov - 11 Nov
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

The Putney Inn

The Putney Inn

10/10 Excellent
"Quiet, clean, safe area. Good breakfast- fruit, yogurt, waffles plus all the usual cereal, toast etc."
Martha 1-night trip
Posted 1 hour ago
The Putney Inn

Frequently asked questions

Searching for B&Bs in Winchester?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B 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 the best choice for your stay?
Every B&B has its own unique feel. Whether it's a cozy reading space or a beautiful breakfast room, the tiny 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 yard. Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the downtown core. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.Inn on Putney Road: 6 rooms. Located 10.7 mi (17.3 km) from the core of Winchester. Enjoy the free full breakfast and onsite spa services.
What's the best time of year to book my B&B in Winchester?
When you're dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches 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 might 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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