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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

B&B in Winsted

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, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is AED 386
AED 443 total
includes taxes & fees
9 Dec - 10 Dec
Locust Tree Bed and Breakfast LLC
Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

3.0 star property
Granby
9.6 out of 10, Exceptional, (101)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is AED 514
AED 571 total
includes taxes & fees
9 Dec - 10 Dec
Truman Gillet House Bed & Breakfast
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is AED 604
AED 694 total
includes taxes & fees
9 Dec - 10 Dec
Blackberry River Inn
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is AED 735
AED 821 total
includes taxes & fees
1 Jan - 2 January 2026
Granville House
Front of property
Simsbury 1820 House

Simsbury 1820 House

4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1000)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is AED 584
AED 735 total
includes taxes & fees
9 Dec - 10 Dec
Simsbury 1820 House
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
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
The price is AED 559
AED 625 total
includes taxes & fees
16 Dec - 17 Dec
Wilder House Berkshires
Interior detail
Manor House Inn

Manor House Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (138)
"Excellent bed and breakfast, room was clean and comfortable."
United States
Kevin
The price is AED 1,184
AED 1,314 total
includes taxes & fees
14 Dec - 15 Dec
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

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

10/10 Excellent
"Clean facility "
Lisa 1-night trip
Posted 22 hours 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. Blackberry River Inn: 14 rooms. Situated 11 mi (17.7 km) from the heart of Winsted. Enjoy the free cooked breakfast and outdoor pool. Locust Tree Bed and Breakfast LLC: 7 rooms. 14.3 mi (23 km) from the heart of downtown.
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 Burr Pond State Park and Northwestern Connecticut Community College Library 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.