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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Winchester bed & breakfast

Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is AED 445
AED 482 total
includes taxes & fees
26 Jan - 27 Jan
The Carriage Barn Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AED 545
AED 600 total
includes taxes & fees
26 Jan - 27 Jan
The One Cat B&B
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (343 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AED 538
AED 592 total
includes taxes & fees
23 Feb - 24 Feb
Colonel Williams Inn
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (278 reviews)
"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "
United States
E S
Monadnock Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AED 862
AED 948 total
includes taxes & fees
25 Jan - 26 Jan
Inn on Putney Road
Free daily full breakfast

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is AED 691
AED 731 total
includes taxes & fees
1 Feb - 2 Feb
Centennial House
Exterior

The Engel House

The Engel House
3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17 reviews)
"The perfect Vermont Bed and Breakfast. "
United States
Lee
The Engel House
Terrace/patio

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 939
AED 939 total
includes taxes & fees
5 Feb - 6 Feb
The Maguire House Bed & Breakfast
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is AED 1,129
AED 1,225 total
includes taxes & fees
1 Feb - 2 Feb
Chesterfield Inn
Outdoor dining

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 1,296 total
includes taxes & fees
31 Jan - 1 Feb
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 Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Staff and room were great! "
Casey 1-night trip
Posted 10 hours ago
The Colonial Hotel

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, Barden State Wildlife Management Area 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: Colonel Williams Inn: 9 rooms. Situated 18.2 mi (29.3 km) from the heart of Winchester. Enjoy the local cuisine breakfast and library. Monadnock Inn: 11 rooms. 17.2 mi (27.6 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, Cass Pond and Barden State Wildlife Management Area are some notable spots. You might put New England Sweetwater Farm & Distillery and Bennett Gorge on your list if you want to see more of the area.