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B&B in Winchester

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (339)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
$150 nightly
The price is $166
Nov 25 - Nov 26
Total with taxes and fees
Colonel Williams Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (11)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$125 nightly
The price is $137
Dec 1 - Dec 2
Total with taxes and fees
Four Columns Inn

The Carriage Barn Inn

3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
$170 nightly
The price is $185
Dec 15 - Dec 16
Total with taxes and fees
The Carriage Barn Inn

Centennial House

3.5 star property
Northfield
9.6 out of 10, Exceptional, (172)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
$195 nightly
The price is $207
Nov 24 - Nov 25
Total with taxes and fees
Centennial House

Inn on Putney Road

4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
$267 nightly
The price is $294
Nov 19 - Nov 20
Total with taxes and fees
Inn on Putney Road

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
$248 nightly
The price is $273
Nov 23 - Nov 24
Total with taxes and fees
The One Cat B&B

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (274)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
$148 nightly
The price is $161
Nov 19 - Nov 20
Total with taxes and fees
Monadnock Inn

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"A very quaint property. The room was comfortable and clean."
United States
Frank
$193 nightly
The price is $211
Nov 19 - Nov 20
Total with taxes and fees
The Engel House

Green River Bridge Inn

3.0 star property
Guilford
8.4 out of 10, Very Good, (13)
"Beautiful Inn and property"
United States
JaDean
$261 nightly
The price is $285
Nov 19 - Nov 20
Total with taxes and fees
Green River Bridge Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Nov 23 - Nov 24
Total with taxes and fees
Chesterfield Inn

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

Guilford
$315 nightly
The price is $353
Nov 25 - Nov 26
Total with taxes and fees
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

Find out more about Winchester

Winchester B&B information

Number of reviews
1,028
Accommodation
12 B&B
Lowest Price
$137
Highest Price
$353

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 $137 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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