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
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Winchester bed & breakfast

Free daily continental breakfast

1. 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 ￥21,884
￥23,744 total
includes taxes & fees
Aug 19 - Aug 20
The Carriage Barn Inn
Front of property

2. 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 ￥39,830
￥43,813 total
includes taxes & fees
Aug 24 - Aug 25
The One Cat B&B
Front of property

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 ￥24,215
￥26,636 total
includes taxes & fees
Aug 23 - Aug 24
Colonel Williams Inn
Front of property - evening/night

4. 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 ￥47,978
￥52,057 total
includes taxes & fees
Aug 18 - Aug 19
Chesterfield Inn
Exterior

5. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (59 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is ￥46,958
￥51,655 total
includes taxes & fees
Aug 20 - Aug 21
Inn on Putney Road
Land view from property

6. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (50 reviews)
"Can’t go wrong with this place."
United States
John
The price is ￥23,703
￥25,836 total
includes taxes & fees
Aug 25 - Aug 26
Four Columns Inn
Exterior

7. Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (290 reviews)
"Castine is a great host, and the inn has a lot of New England charm. Great place to stay!"
United States
Saif
The price is ￥26,219
￥28,448 total
includes taxes & fees
Aug 18 - Aug 19
Monadnock Inn
Outdoor dining

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
The price is ￥43,813
￥56,030 total
includes taxes & fees
Aug 23 - Aug 24
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Terrace/patio

9. 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 ￥44,044
￥44,044 total
includes taxes & fees
Aug 26 - Aug 27
The Maguire House Bed & Breakfast
Exterior

10. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (176 reviews)
"David was incredibly hospitable. I thoroughly enjoyed my stay. "
United States
Amy
The price is ￥27,451
￥29,016 total
includes taxes & fees
Aug 18 - Aug 19
Centennial House
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

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

8/10 Good
"Friendly staff, clean lobby and adequate rooms."
Michelle 2-night trip
Posted 5 hours ago
Hampton Inn & Suites Greenfield

Find out more about Winchester

Winchester B&B information

Number of reviews
1,334
Accommodation
12 B&B
Lowest Price
￥23,744
Highest Price
￥52,057

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 B&Bs in the area: Monadnock Inn: 11 rooms. 17.2 mi (27.6 km) from the downtown core. Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the heart of downtown.Centennial House: 5 rooms. Located 6.4 mi (10.3 km) from the core of Winchester. Enjoy the free full breakfast and unique décor.
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, Cass Pond and Loring Field are some notable spots. You might put Winchester Speedpark and Pisgah State Park on your list if you want to see more of the area.

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