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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 12 B&B in Winchester with updated reviews, rates, and availability.

The Maguire House Bed & Breakfast
Property grounds

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
Jul 17 - Jul 18
Total includes taxes and fees
The Maguire House Bed & Breakfast
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"Hi it’s a beautiful inn and very comfortable "
$176 nightly
The price is $191
Jun 29 - Jun 30
Total includes taxes and fees
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (150)
"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."
$201 nightly
The price is $218
Jul 1 - Jul 2
Total includes taxes and fees
The Carriage Barn Inn
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (153)
"This historic property is very nice. Beds are comfortable. The hosts are very welcoming and communication was very good. Breakfast was outstanding! I highly recommend this property and hope to return for another visit someday. "
$153 nightly
The price is $162
Jun 30 - Jul 1
Total includes taxes and fees
Centennial House
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
$301 nightly
The price is $327
Jul 6 - Jul 7
Total includes taxes and fees
Chesterfield Inn
The One Cat B&B
Exterior

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!"
$214 nightly
The price is $236
Jul 27 - Jul 28
Total includes taxes and fees
The One Cat B&B
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (46)
"The breakfast was excellent and Paul did whatever he could to enhance our stay "
$265 nightly
The price is $292
Jul 1 - Jul 2
Total includes taxes and fees
Inn on Putney Road
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Outdoor dining

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

$252 nightly
The price is $282
Jul 5 - Jul 6
Total includes taxes and fees
Private bedroom in the Green River Bridge Inn. A full breakfast is included.
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
10.0 out of 10, Exceptional, (1)
"Such a peaceful, beautiful area and inn! The host is wonderful and an amazing cook. The quintessential Vermont inn with an international flair. Can’t wait to go back!"
$203 nightly
The price is $221
Jun 29 - Jun 30
Total includes taxes and fees
Green River Bridge Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
$148 nightly
The price is $162
Jul 27 - Jul 28
Total includes taxes and fees
Colonel Williams Inn
The Engel House
Exterior

The Engel House

3.0 star property
9.2 out of 10, Wonderful, (12)
"The perfect Vermont Bed and Breakfast. "
$193 nightly
The price is $211
Jun 29 - Jun 30
Total includes taxes and fees
The Engel House
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 $162 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.