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Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
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Dec 12 - Dec 14
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B&B in Winsted

Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

3.0 star property
Granby
9.6 out of 10, Exceptional, (99)
"It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice."
United States
Lynn
$140 nightly
The price is $155
Nov 17 - Nov 18
Total with taxes and fees
Truman Gillet House Bed & Breakfast
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (410)
"Peaceful area and great staff; Thank you for the service and experience "
United States
Andre
$105 nightly
The price is $121
Nov 17 - Nov 18
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
$144 nightly
The price is $161
Nov 16 - Nov 17
Total with taxes and fees
Wilder House Berkshires
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (157)
"Very good breakfast.excellent waiter.love the atmosphere."
United States
Marc
$161 nightly
The price is $186
Nov 24 - Nov 25
Total with taxes and fees
Blackberry River Inn
Front of property
Simsbury 1820 House

Simsbury 1820 House

4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Adorable bed and breakfast with a nice bar/restaurant. The staff were very accommodating. "
United States
Chantel
$194 nightly
The price is $223
Nov 16 - Nov 17
Total with taxes and fees
Simsbury 1820 House
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (87)
"I’m a former travel writer and hotel reviewer at the NY Times Sunday Travel and I’ve been coming to the Berkshires the past decade. This is the hands down the best B&B in the area. The decor, the ambiance, the artistic details, the warm customer service, the made-to-order gourmet breakfast next to a wood-burning fireplace - all make this place so cozy and truly unique. Listen to the jukebox or play billiards in the inn’s great room. Or lounge beneath the heat lamps on its wraparound porch. You...
United States
Lionel
$199 nightly
The price is $222
Nov 21 - Nov 22
Total with taxes and fees
Granville House
Interior detail
Manor House Inn

Manor House Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"A charming old manor from the Gilded Age, thoughtfully updated and modernized without losing the soul of the original home. Incredibly comfortable rooms, inviting common spaces, excellent breakfast, beautiful grounds, and friendly staff. We especially enjoyed the fireplace in our room. Perfect for a romantic getaway, we look forward to visiting again in the future."
United States
Anonymous traveler
$297 nightly
The price is $330
Dec 7 - Dec 8
Total with taxes and fees
Manor House Inn
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 Winsted Hotel Reviews

DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

10/10 Excellent
"Bar was good "
Kevin 1-night trip
Posted 13 hours ago
DoubleTree by Hilton Hartford - Bradley Airport

Find out more about Winsted

Winsted B&B information

Number of reviews
1,895
Accommodation
10 B&B
Lowest Price
$121
Highest Price
$330

Frequently asked questions

What are the most popular Winsted B&Bs?
Rock Hall Luxe Lodging is an exceptional choice for travelers seeking a memorable stay in Winsted, boasting an impressive 10.0 rating. Guests rave about the tranquil ambiance and the luxurious features, including a delightful hot tub that provides the superb way to unwind after a day of exploration. This property's attentive service and inviting space make it ideal for couples looking for a romantic getaway or solo travelers wanting to relax in style.
What is the nightly rate for a Bed & Breakfast in Winsted?
Prices for B&Bs in Winsted often vary, but you can find a great deal from $121 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winsted 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 Bed and Breakfast in Winsted?
The best time to book a B&B in Winsted is during the vibrant summer months, particularly from May to July, when visitors flock to enjoy the area's stunning natural beauty and outdoor activities. This peak season is particularly appealing to those who appreciate sunny days superb for hiking, boating, and exploring the charming local parks.

July stands out as the most popular month, offering warm temperatures that typically range from the mid-60s to the low 80s Fahrenheit. This is an ideal time for outdoor enthusiasts, as the lush surroundings invite leisurely walks or exhilarating bike rides along the scenic trails. Additionally, Winsted's community often hosts engaging events and festivals, adding to the lively atmosphere.

For travelers looking for a more budget-friendly experience, consider planning your visit in October. This month showcases the breathtaking fall foliage, creating a picturesque backdrop for enjoying the crisp air and vibrant colors. The quieter ambiance allows for more intimate experiences, whether it's exploring local shops or savoring delicious meals at cozy restaurants.
What is the difference between a Winsted Bed & Breakfast and a hotel?
Every Winsted 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 Winsted B&Bs.

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