20 Best B&B in Winchester, NH - Bed and Breakfast from ￥19,376

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Our top choices for Winchester bed & breakfast

A sign for the Centennial House, indicating it is a bed and breakfast with a historical theme, established in 1811.

1. Centennial House

Northfield

Alan

￥29,389 total

includes taxes & fees

Nov 18 - Nov 19

A wooden table set with plates, cutlery, and a folded napkin.

2. The Carriage Barn Inn

Keene

Richard

￥21,023 total

includes taxes & fees

Dec 16 - Dec 17

A traditional white building with black shutters, a stone pathway leading to the entrance, and a signboard advertising a breakfast buffet.

3. Inn on Putney Road

Brattleboro

Karla

￥46,893 total

includes taxes & fees

Nov 16 - Nov 17

A grassy outdoor area with two Adirondack chairs under a tree, a small building, and a road in the background.

4. Chesterfield Inn

West Chesterfield

Wayne

￥52,184 total

includes taxes & fees

Nov 17 - Nov 18

A large white building with a stone wall and a lawn covered in fallen leaves.

5. Colonel Williams Inn

Brattleboro

Amy

￥30,419 total

includes taxes & fees

Nov 22 - Nov 23

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

6. Four Columns Inn

Newfane

Raymond

￥26,445 total

includes taxes & fees

Nov 24 - Nov 25

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

Jaffrey

Jim

￥21,075 total

includes taxes & fees

Nov 16 - Nov 17

A table with various food items and a bottle of wine, overlooking a lush garden.

8. Private bedroom in the Green River Bridge Inn. A full breakfast is included.

Guilford

￥53,483 total

includes taxes & fees

Nov 22 - Nov 23

A cozy living room with a sofa, armchairs, a coffee table, and a TV. There are wooden walls and a ceiling fan.

9. Amazing People & Pet-Welcoming Country Haven

Charlemont

Pat O.

￥42,457 total

includes taxes & fees

Nov 16 - Nov 17

A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

10. The Maguire House Bed & Breakfast

Ashburnham

Jeffrey

￥45,062 total

includes taxes & fees

Dec 2 - Dec 3

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Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester

A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

Top reviews in Winchester

Centennial House

Northfield

10/10 Excellent

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

Chesterfield Inn

West Chesterfield

10/10 Excellent

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

Four Columns Inn

Newfane

10/10 Excellent

Nettie

The Maguire House Bed & Breakfast

Ashburnham

10/10 Excellent

Anonymous traveler

Monadnock Inn

Jaffrey

10/10 Excellent

On a Foliage tour through New England in October, my wife and I stayed at The Monadnock Inn following a hike of the nearby Mt. Monadnock. Arrival mid-week was simple and the Inn is full of centuries-old charm and comfort. Check-in was very simple and we were handed a key and walked up the stairs to the 3rd Floor Pauline Room. The room was very cozy with an antique soak tub and shower (great after a long hike), beautiful bay windows, steam radiator, comfortable bed, and warmly lit. There was no...

Todd

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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Find Winchester Bed And Breakfast

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester bed & breakfast

1. Centennial House

2. The Carriage Barn Inn

3. Inn on Putney Road

4. Chesterfield Inn

5. Colonel Williams Inn

6. Four Columns Inn

7. Monadnock Inn

8. Private bedroom in the Green River Bridge Inn. A full breakfast is included.

9. Amazing People & Pet-Welcoming Country Haven

10. The Maguire House Bed & Breakfast

Learn more about Winchester

Top reviews in Winchester

Centennial House

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Winchester?

How do you know if a B&B is the best choice for your stay?

What are the best B&Bs in Winchester?

What's the best time of year to book my B&B in Winchester?

What is there to do in Winchester?

Explore a world of travel with Expedia