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
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul
In one month
17 Jul - 19 Jul
In two months
14 Aug - 16 Aug

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, (111 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
The price is AED 514
AED 571 total
includes taxes & fees
23 Jun - 24 Jun
Truman Gillet House Bed & Breakfast
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (55 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AED 623
AED 695 total
includes taxes & fees
23 Jun - 24 Jun
Wilder House Berkshires
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, (423 reviews)
"Below average B&B"
United States
Larry
The price is AED 386
AED 444 total
includes taxes & fees
22 Jun - 23 Jun
Locust Tree Bed and Breakfast LLC
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
"beautiful inn"
United States
Maura
The price is AED 532
AED 612 total
includes taxes & fees
28 Jun - 29 Jun
Blackberry River Inn
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (7 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 AED 908
AED 1,014 total
includes taxes & fees
22 Jun - 23 Jun
The Berkshire Mountain Inn
Exterior

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful historical hotel Room was lovely Staff friendly and helpful"
United States
FRANK
The price is AED 878
AED 1,073 total
includes taxes & fees
22 Jun - 23 Jun
Simsbury 1820 House
Exterior detail

Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
9.0 out of 10, Wonderful, (2 reviews)
"We had a very comfortable stay . Communication with our host was easy & prompt. We would stay again “"
United States
Laurel B.
The price is AED 555
AED 711 total
includes taxes & fees
22 Jun - 23 Jun
Peaceful Modern Private Room with Comfort & Charm
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 AED 1,045
AED 1,160 total
includes taxes & fees
1 Jul - 2 Jul
Manor House 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 AED 2,615
AED 3,008 total
includes taxes & fees
3 Jul - 4 Jul
Sunny Peace Homestay
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

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent
"Always pleasantly surprised with HIEs but this one was in a league of its own. 11/10"
Dan 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Bradley Airport by IHG

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 Rowley Fields and Highland Lake if you're hoping to see some of the area's natural features. You might put Burr Pond State Park and Laurel Lanes 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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