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Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
In one month
Dec 12 - Dec 14
In two months
Jan 9 - Jan 11

B&B in Winchester

Exclusive Room | Premium bedding, Tempur-Pedic beds, individually decorated
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.6 out of 10, Exceptional, (10)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
$125 nightly
The price is $137
Nov 20 - Nov 21
Total with taxes and fees
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, (164)
"This BNB is delightful. Great location and easy to find in town. Lovely house, room, easy check in, and the owner was great. The owner was there when we checked in and gave us a tour and recommendations for dinner in town. Downtown is just darling and easy walking around the town square. Dinner in town was excellent as well. I would highly recommend a stay here to anyone. "
United States
Tina
$170 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
The Carriage Barn Inn
Front of property
Colonel Williams Inn

Colonel Williams Inn

3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (338)
"Very charming place. Breakfast was really good, made fresh, very accommodating with food intolerances. Very much enjoyed my stay."
Canada
Carolyn
$148 nightly
The price is $163
Nov 30 - Dec 1
Total with taxes and fees
Colonel Williams Inn
Free daily full breakfast
Centennial House

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
$199 nightly
The price is $210
Nov 16 - Nov 17
Total with taxes and fees
Centennial House
Exterior
Inn on Putney Road

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 16 - Nov 17
Total with taxes and fees
Inn on Putney Road
Property grounds
The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast

3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The Maguire House Bed & Breakfast
Exterior
The One Cat B&B

The One Cat B&B

2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"We loved our stay! Very welcoming and cozy. The breakfast was delicious. Will definitely come back to stay here again!"
United States
Wiley
$245 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
The One Cat B&B
Exterior
The Engel House

The Engel House

3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"Warm and inviting atmosphere. Great location. "
United States
Diane
$193 nightly
The price is $211
Nov 16 - Nov 17
Total with taxes and fees
The Engel House
Exterior
Monadnock Inn

Monadnock Inn

2.5 star property
Jaffrey
7.6 out of 10, Good, (273)
"The owners are the best. Wonderful place, made with love. "
United States
Adele
$148 nightly
The price is $161
Nov 14 - Nov 15
Total with taxes and fees
Monadnock Inn
Exterior
Green River Bridge Inn

Green River Bridge Inn

3.0 star property
Guilford
8.4 out of 10, Very Good, (13)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
United States
Melissa
$258 nightly
The price is $282
Dec 14 - Dec 15
Total with taxes and fees
Green River Bridge Inn
Lobby
Chesterfield Inn

Chesterfield Inn

4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."
United States
Susan
$301 nightly
The price is $327
Nov 16 - Nov 17
Total with taxes and fees
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
$315 nightly
The price is $353
Nov 20 - Nov 21
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

The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
Christine 2-night trip
Posted 3 days ago
The Inn At Crumpin Fox

Find out more about Winchester

Winchester B&B information

Number of reviews
1,058
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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