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B&B in Winchester

Green River Bridge Inn

3.0 star property
8.4 out of 10, Very Good, (7)
"The area is beautiful and the inn is lovely. I would highly recommend to anyone visiting the area. "
$221 nightly
The price is $240
Aug 19 - Aug 20
Total includes taxes and fees
Green River Bridge Inn

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (313)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
$156 nightly
The price is $172
Aug 31 - Sep 1
Total includes taxes and fees
Colonel Williams Inn

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (267)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
$176 nightly
The price is $191
Aug 19 - Aug 20
Total includes taxes and fees
Monadnock Inn

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (160)
"Lovely property and innkeepers, I was in the area for an event and hope to come back. "
$224 nightly
The price is $237
Aug 25 - Aug 26
Total includes taxes and fees
Centennial House

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
$295 nightly
The price is $324
Aug 18 - Aug 19
Total includes taxes and fees
Inn on Putney Road

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
$198 nightly
The price is $218
Aug 27 - Aug 28
Total includes taxes and fees
The One Cat B&B

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
$187 nightly
The price is $203
Sep 15 - Sep 16
Total includes taxes and fees
The Carriage Barn Inn

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
$301 nightly
The price is $327
Aug 25 - Aug 26
Total includes taxes and fees
Chesterfield Inn

The Engel House

3.0 star property
9.4 out of 10, Exceptional, (13)
"The perfect Vermont Bed and Breakfast. "
$193 nightly
The price is $211
Aug 17 - Aug 18
Total includes taxes and fees
The Engel House

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
$275 nightly
The price is $275
Sep 10 - Sep 11
Total includes taxes and fees
The Maguire House Bed & Breakfast

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
$195 nightly
The price is $213
Aug 17 - Aug 18
Total includes taxes and fees
Four Columns Inn

The Brattleboro

4.0 star property
10.0 out of 10, Exceptional, (5)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro
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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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 $172 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.