Search B&B in Winchester

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Our top choices for Winchester bed & breakfast

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (36 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AED 479
AED 522 total
includes taxes & fees
18 May - 19 May
Four Columns Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (353 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AED 532
AED 585 total
includes taxes & fees
14 May - 15 May
Colonel Williams Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is AED 625
AED 678 total
includes taxes & fees
11 May - 12 May
The Carriage Barn Inn

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 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 AED 953
AED 953 total
includes taxes & fees
20 May - 21 May
The Maguire House Bed & Breakfast

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AED 891
AED 980 total
includes taxes & fees
24 May - 25 May
The One Cat B&B

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is AED 1,043
AED 1,148 total
includes taxes & fees
12 May - 13 May
Inn on Putney Road

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (281 reviews)
"This is a good representation of staying in an inn of the 1969s. "
United States
Frank
The price is AED 604
AED 656 total
includes taxes & fees
17 May - 18 May
Monadnock Inn

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is AED 1,106
AED 1,200 total
includes taxes & fees
14 May - 15 May
Chesterfield Inn

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 AED 1,010
AED 1,288 total
includes taxes & fees
13 May - 14 May
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

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, Rhododendron State Park and Loring Field 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: The Carriage Barn Inn: 4 rooms. 11.8 mi (18.9 km) from the downtown core. Monadnock Inn: 11 rooms. Situated 17.2 mi (27.6 km) from the heart of Winchester. Centennial House: 5 rooms. 6.4 mi (10.3 km) from the heart of downtown. Enjoy the free full breakfast and unique décor. Colonel Williams Inn: 9 rooms. Located 18.2 mi (29.3 km) from the core of Winchester. Enjoy the local cuisine breakfast and library.
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, Rhododendron State Park and Birch Point 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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