Photo by Kim Knox Beckius

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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (953)
"Loved the history of the building. "
The price is HK$1,234
HK$1,552 total
includes taxes & fees
30 Apr - 1 May
Simsbury 1820 House
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (100)
"It was an amazing stay. Lucas is the most pleasant, kind and helpful B&B host. "
The price is HK$1,290
HK$1,483 total
includes taxes & fees
5 May - 6 May
Blackberry River Inn
Wilder House Berkshires
Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (21)
"Bert was great - he really tried to help after the Expedia website (and app) made it impossible for me to cancel my trip (my wife and I came down with Influenza A). There was little he could do as I had booked through Expedia. I ended up paying full price and am finding it impossible to communicate with Expedia..."
The price is HK$1,187
HK$1,326 total
includes taxes & fees
28 Apr - 29 Apr
Wilder House Berkshires
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (377)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is HK$815
HK$937 total
includes taxes & fees
27 Apr - 28 Apr
Locust Tree Bed and Breakfast LLC
Truman Gillet House Bed & Breakfast
Property grounds

Truman Gillet House Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (87)
"It is a very charming place. I would recommend it."
The price is HK$1,009
HK$1,120 total
includes taxes & fees
2 May - 3 May
Truman Gillet House Bed & Breakfast
Manor House Inn
Interior detail

Manor House Inn

3.0 star property
9.2 out of 10, Wonderful, (135)
"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."
The price is HK$2,411
HK$2,677 total
includes taxes & fees
22 May - 23 May
Manor House Inn
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Phenomenal hospitality, eclectic decor, luxurious sleep - we have been raving about our stay and will definitely be back!"
The price is HK$1,738
HK$1,941 total
includes taxes & fees
30 Apr - 1 May
Granville House
Sunny Peace Homestay
Living room

Sunny Peace Homestay

3.0 star property
9.4 out of 10, Exceptional, (3)
"A beautiful home in the woods of Northwest Connecticut. Quiet. Responsive and pleasant customer service. "
Sunny Peace Homestay
Green Acres B&B
Seasonal outdoor pool

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres B&B
Rock Hall Luxe Lodging
Outdoor pool

Rock Hall Luxe Lodging

4.5 star property
10.0 out of 10, Exceptional, (4)
"The innkeepers were extememly accomadating. They made dinner reservations for us and offered suggestions of activities. Breakfast was fantastic. Before we left, we picked apples from the onsite orchard. Highly reccomended."
Rock Hall Luxe Lodging
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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Other property types in Winsted

The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beach nearby, sun-loungers, beach towels

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beach

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

10.0 out of 10, Exceptional, (92)
"The spacious house and view of the frozen lake were wonderful for our family gathering. It was unfortunate the hot tub was broken and there were some water issues, but the hostess was gracious in trying to accommodate us. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (24)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock
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.

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.
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 Platt Hill State Park and Burr Pond State Park 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.