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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

Compare 10 B&B in Winsted with updated reviews, rates, and availability.

Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (951)
"Our room was beautiful and very clean. Loved the four poster bed, the white and blue toile wallpaper, and the numerous windows. The bedroom and bathroom were both a very good size. The continental breakfast offered a selection of coffees and a delicious assortment of breakfast breads, scones and bagels. The sitting room is very charming. Enjoyed our stay and will be returning. "
The price is SAR 597
SAR 751 total
includes taxes & fees
14 Apr - 15 Apr
Simsbury 1820 House
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (99)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is SAR 624
SAR 718 total
includes taxes & fees
5 May - 6 May
Blackberry River Inn
Wilder House Berkshires
Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (19)
"It's a boutique B&B place with 5 rooms with great interior decoration. Brad, the owner has an innate focus for details, which shows up in his communications and design of the property and room, including the naming of the inn (Wilder Oak is the name of his 3 years old son...). Brad is relatively new in the hospitality industry, but his intentions and mannerism are just right for the place. He cooks breakfast for guests in the weekend; design of the menue card and breakfast choices are just right...
The price is SAR 613
SAR 684 total
includes taxes & fees
6 May - 7 May
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, (376)
"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 SAR 394
SAR 453 total
includes taxes & fees
12 Apr - 13 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 SAR 488
SAR 542 total
includes taxes & fees
17 Apr - 18 Apr
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."
Manor House Inn
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is SAR 747
SAR 835 total
includes taxes & fees
20 Apr - 21 Apr
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!
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (18)
"A great winter getaway in the Berkshires. We loved the location of this very nice spot in Great Barrington. Had some great dinners we could walk to and we were able to do amazing hikes during the day and visit other spots around GB as well. Would definitely recommend! House is clean and has a nice vibe and beds comfortable. Nice shower too!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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 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 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?
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.