A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

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Check prices for these dates

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19
In one month
Jul 31 - Aug 2
In two months
Aug 28 - Aug 30

Our top choices for Winsted bed & breakfast

Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (112 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
The price is P8,619
P9,567 total
includes taxes & fees
Jul 5 - Jul 6
Truman Gillet House Bed & Breakfast
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (427 reviews)
"Below average B&B"
United States
Larry
The price is P6,464
P7,434 total
includes taxes & fees
Jul 7 - Jul 8
Locust Tree Bed and Breakfast LLC
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is P10,681
P11,931 total
includes taxes & fees
Jul 7 - Jul 8
Wilder House Berkshires
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
"beautiful inn"
United States
Maura
The price is P9,585
P11,023 total
includes taxes & fees
Jul 5 - Jul 6
Blackberry River Inn
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
The price is P7,591
P12,269 total
includes taxes & fees
Jul 19 - Jul 20
Sunny Peace Homestay
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is P16,302
P18,209 total
includes taxes & fees
Jul 15 - Jul 16
The Berkshire Mountain Inn
Exterior

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,001 reviews)
"Beautiful historical hotel Room was lovely Staff friendly and helpful"
United States
FRANK
The price is P14,714
P17,983 total
includes taxes & fees
Jul 5 - Jul 6
Simsbury 1820 House
Front of property

Manor House Inn

Manor House Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (139 reviews)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is P21,510
P23,876 total
includes taxes & fees
Jul 5 - Jul 6
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The rooms were clean and it is a good location for several restaurants. The staff was very friendly and helpful. When I realized there was no pool, the person at the desk told me of a pool about two miles away. We got a pass for our grandson and he had a great time."
Rosanna 1-night trip
Posted 13 hours ago
Quality Inn Great Barrington

Find out more about Winsted

Winsted B&B information

Number of reviews
1,942
Accommodation
10 B&B
Lowest Price
P7,434
Highest Price
P23,876

Frequently asked questions

Searching for B&Bs in Winsted?
If you're looking for something a little more offbeat than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your vacation. If your ideal vacation to Winsted includes spending lots of time outside, Rowley Fields and Walker Field are good spots to enjoy the scenery.
How do you know if a B&B is the best choice for you?
With attentive service, opportunities to meet guests from other places, and breakfast served on site, B&Bs all have a unique setting.
What are the best bed and breakfasts in Winsted?
Here are some well-liked B&Bs in the area: Rock Hall Luxe Lodging: 5 rooms. 5.9 mi (9.4 km) from the heart of Winsted. Enjoy the free full breakfast and fitness center. Simsbury 1820 House: 13.7 mi (22 km) from the downtown core. Enjoy the designer toiletries and bars. Locust Tree Bed and Breakfast LLC: 7 rooms. Situated 14.3 mi (23 km) from the heart of Winsted. Blackberry River Inn: 14 rooms. 11 mi (17.7 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool.
When should I book my B&B in Winsted?
When you're dreaming of a stay in Winsted, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winsted are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Winsted?
Spend some time exploring Highland Lake and Rowley Fields if you're hoping to see some of the area's natural features. You might put The Marina at Highland Lake and Platt Hill State Park on your list if you want to see more of the area.
How can I get to and around Winsted?
Planning your excursions in and around Winsted is easier with these transportation options. Fly into Bradley Intl. Airport (BDL), which is located 19.3 mi (31 km) away from the city center. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 24.5 mi (39.4 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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