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Aug 15 - Aug 17
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Browse Select Winsted Vacation Homes

Spacious Home nestled along the Blackberry River in Northwest CT
Enjoy cooking and dining in this well-equipped kitchen with a central island, appliances, and a dining area that opens to a deck with a grill.

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT
Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is CA $275
CA $499 total
includes taxes & fees
Aug 11 - Aug 12
Big farmhouse in the foothills of the Berkshires
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding landscape.

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is CA $357
CA $624 total
includes taxes & fees
Aug 10 - Aug 11
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Tranquil Litchfield Connecticut Retreat".
Relax by the fire pit in a serene outdoor seating area surrounded by Adirondack chairs.

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (15)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is CA $309
CA $439 total
includes taxes & fees
Aug 10 - Aug 11
Tranquil Litchfield Connecticut Retreat".
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Lake Congamond Cozy Stylish Comfortable House
Enjoy a serene lakeside retreat with a boat dock and tranquil views.

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Private Annex/Former Artist Studio
Relax on the deck overlooking a lush garden with a tranquil atmosphere.

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"Great property great location wonderful day"
Private Annex/Former Artist Studio
Spectacular views and close to Great Barrington.
Relax in this inviting living area with a high ceiling, brick fireplace, and expansive windows offering views of the surrounding landscape.

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
Relax or be active! The choice is yours in this pet-friendly family home.
Enjoy cooking in this well-equipped kitchen with a central island, stovetop, and ample counter space.

Relax or be active! The choice is yours in this pet-friendly family home.

10.0 out of 10, Exceptional, (13)
"Home was exactly as listed, very comfortable and convenient for my family’s trip. "
Relax or be active! The choice is yours in this pet-friendly family home.
Charming 1870 cape cottage in Litchfield
Relax by the pool surrounded by lush greenery and a serene water feature.

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (52)
"Property was great and the owners thought of everything. Instructions were clear and helpful! Didn’t want for a thing, such a lovely space to spend a few days and so close to Litchfield and Bantam shops and restaurants. We loved it!! "
Charming 1870 cape cottage in Litchfield
Woodland A-Frame
Spacious living area with a high ceiling, stone accent wall, and kitchen island.

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Mountaintop Horse Farm with Heated Pool
Relax by the pool surrounded by lush greenery and a traditional house in the background.

Mountaintop Horse Farm with Heated Pool

10.0 out of 10, Exceptional, (31)
"This a the most unique place! A very clean and comfortable apartment above a barn with beautiful horses and more. Wonderful hosts too. We hope to be back! "
Mountaintop Horse Farm with Heated Pool
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Relax by the fire pit in a serene forest setting, surrounded by comfortable seating.

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The price is CA $374
CA $684 total
includes taxes & fees
Aug 18 - Aug 19
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Cozy Lakefront Bungalow w firepit/dock/kayaks
Enjoy the view from the upper balcony, which offers a fire pit and Adirondack chairs in the yard.

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (5)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Enjoy a well-equipped kitchen with a central sink, stainless steel faucet, and a window offering a view of the surrounding greenery.

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (27)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and large window offering a view of the outdoors.

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Quiet Cabin On Over 12 Acres Of Woods!
Cozy living space with a central island kitchen, spiral staircase, and comfortable seating area.

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (11)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Enjoy a formal outdoor dining experience surrounded by lush greenery and tall trees.

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (8)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
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

Delamar West Hartford

Delamar West Hartford

10/10 Excellent
"This hotel was excellent from the time we pulled up at the valet until we left 2 days later. I am an ice person and there is no ice machine, but they brought it up immediately when I called. Check in was seamless and the bar was awesome as well as the breakfast! Definitely would stay again. The little town Square that is right across from it was also very quaint. Lots of shops and restaurants."
Maureen 2-night trip
Posted 16 hours ago
Delamar West Hartford