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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Winsted bed & breakfast

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

1. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (256 reviews)
"Great Breakfast Bed was okay Room very quaint hotel was very nice inside"
United States
Melanie
The price is AU$307
includes taxes & fees
22 Nov - 23 Nov
Blackberry River Inn
A covered porch with white railings, a rocking chair, and hanging flower baskets.

2. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (455 reviews)
"Wonderful stay, and wonderful breakfast."
United States
Daniel
The price is AU$176
includes taxes & fees
14 Nov - 15 Nov
Locust Tree Bed and Breakfast LLC
A large, historic building with a covered porch and outdoor seating area.

3. Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.4 out of 10, Exceptional, (1,001 reviews)
"Restaurant inside inn was comforting and had a great vibe."
United States
Enrique
The price is AU$276
includes taxes & fees
15 Nov - 16 Nov
Simsbury 1820 House
A rural landscape with a red barn, a green house, and autumn foliage.

4. Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (123 reviews)
"We had a very nice peaceful stay :)"
United States
Melanie
The price is AU$227
includes taxes & fees
14 Nov - 15 Nov
Truman Gillet House Bed & Breakfast
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

5. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.0 out of 10, Wonderful, (19 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is AU$273
includes taxes & fees
18 Nov - 19 Nov
Sunny Peace Homestay
A building with a grey exterior, a front door, and a small porch with steps.

6. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
8.4 out of 10, Very good, (6 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 AU$288
includes taxes & fees
1 Dec - 2 Dec
Peaceful Modern Private Room with Comfort & Charm
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

7. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is AU$267
includes taxes & fees
15 Nov - 16 Nov
Wilder House Berkshires
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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Learn more about Winsted

Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.

See all hotels in Winsted
A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.

Top reviews in Winsted

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
Norfolk

8/10 Good

A beautiful old Inn that has been well looked after. Breakfast was in a beautiful room and the food and service were both excellent. We also appreciated the complimentary cookies and chocolates in the foyer along with the tea and coffee facilities. The not so good points were the strong smell outside from the piggery (?) which thankfully couldn't be smelled from inside the building. Also the walls are paper thin so we were kept up by our neighbours who turned up late and had their TV going....
Australia
Danielle
Reviewed October 7, 2025
Blackberry River Inn

Frequently Asked Questions

Searching for B&Bs in Winsted?

If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. If your ideal holiday 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 right choice for you?

With attentive service, opportunities to interact with the owner and delectable breakfasts, 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 centre. Simsbury 1820 House: 13.7 mi (22 km) from the city centre. 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 city centre. Sunny Peace Homestay: 2 rooms. Located 11.8 mi (19 km) from the core of Winsted.

What's the best time of year to book my B&B in Winsted?

When you're dreaming of a escape to Winsted, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winsted are January, February, March and April, with each month seeing an average of 15 cm 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 should put Burr Pond State Park and The Marina at Highland Lake on your list if you want to see more of the area.

How can I get to and around Winsted?

You can map out your trip in and around Winsted ahead of time with these transportation options. Fly into Hartford, CT (BDL-Bradley Intl.), which is located 19.3 mi (31 km) from the city centre. You can also search 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, consider renting a car to explore more sights.