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
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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, (195 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
$179 nightly
The price is $190
Nov 18 - Nov 19
Total with taxes and fees
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
$138 nightly
The price is $150
Nov 23 - Nov 24
Total with taxes and fees
The Carriage Barn Inn
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

3. 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
$267 nightly
The price is $294
Nov 16 - Nov 17
Total with taxes and fees
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.

4. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Nov 17 - Nov 18
Total with taxes and fees
Chesterfield Inn
A room with two single beds, a desk, and a radiator.

5. 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
$171 nightly
The price is $188
Nov 22 - Nov 23
Total with taxes and fees
Colonel Williams Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

6. 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
$148 nightly
The price is $161
Nov 24 - Nov 25
Total with taxes and fees
Four Columns 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
$122 nightly
The price is $132
Nov 16 - Nov 17
Total with taxes and fees
Monadnock Inn
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.

Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Guilford
2.0 out of 10, (1 review)
$299 nightly
The price is $335
Nov 22 - Nov 23
Total with taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
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

Amazing People & Pet-Welcoming Country Haven
Charlemont
9.8 out of 10, Exceptional, (211 reviews)
"Lovely little cottage with lots of welcoming little comforts and touches. We wish we could have stayed and enjoyed it a little longer. Our whole family (including the dog) enjoyed the stay."
United States
Pat O.
$238 nightly
The price is $266
Nov 16 - Nov 17
Total with taxes and fees
Amazing People & Pet-Welcoming Country Haven
A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

10. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (41 reviews)
"Terry and Paul are wonderful warm Innkeepers. The inn is classically New England charming. The lake view is stunning. Appreciated the little touches like nighty cookies, water and snacks in the room."
United States
Jeffrey
$276 nightly
The price is $276
Dec 2 - Dec 3
Total with taxes and fees
The Maguire House Bed & Breakfast
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Clean room. Nice breakfast ladies. Complimentary Soup in the evening."
Davina 3-night trip
Posted 20 hours ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Find out more about Winchester

Winchester B&B information

Number of reviews
1,216
Accommodation
13 B&B
Lowest Price
$132
Highest Price
$335

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Winchester?
Prices for B&Bs in Winchester often vary, but you can find a great deal from $132 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winchester?
The best time to book a B&B in Winchester is during the vibrant spring months of April to June, when the region comes alive with blooming flowers and outdoor activities. This period is particularly attractive to travelers seeking a mix of history and nature, as the comfortable temperatures, ranging from the mid-50s to the low 80s Fahrenheit, create ideal conditions for exploring the scenic landscapes and historic sites.

April marks the start of a delightful season, with many visitors drawn to Winchester for its picturesque gardens and nearby hiking trails. The famous Appalachian Trail, which runs close to Winchester, offers opportunities for both leisurely walks and more challenging hikes, making it a haven for outdoor enthusiasts. Additionally, spring festivals celebrating local culture add to the charm of the area.

For those looking to enjoy a quieter experience while still taking in the beauty of the region, consider visiting in November. This month often features stunning autumn foliage, ideal for scenic drives and peaceful strolls through Winchester's historic downtown. The fewer crowds create a more relaxed atmosphere, superb for savoring the local cuisine and exploring the rich history of the town.
What is the difference between a Winchester Bed and Breakfast and a hotel?
Every Winchester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winchester B&Bs.

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