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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Browse Select Winsted Apartments

Litchfield Hills Hideaway
Fridge, microwave, oven, stovetop

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (63)
"Wonderful experience! Everything was well appointed and spotless. An extremely enjoyable stay. Thank you "
Litchfield Hills Hideaway
Renovated Apartment on Main St.
Smart TV

Renovated Apartment on Main St.

6.0 out of 10, (2)
"Beautiful natural light, clean and overlooking Main Street in Salisbury. Extremely well equipped with pillows, blankets, towels, clean, new bedding. I imagine an artist writing a song or a novel here. Walkable to shops, a market, grazing sheep and the best cold brew and pastries you can find anywhere. "
Renovated Apartment on Main St.
Steele Brook Manor Tranquil get away nestled in Litchfield County.
Interior

Steele Brook Manor Tranquil get away nestled in Litchfield County.

2.0 star property
9.6 out of 10, Exceptional, (4)
"This apartment in an older home met all of our needs. It was well-equipped and well-furnished, neat and clean, quiet with ample parking. "
Steele Brook Manor Tranquil get away nestled in Litchfield County.
Dugway Hideaway Walking Distance to Lime Rock Park
Outdoor dining

Dugway Hideaway Walking Distance to Lime Rock Park

9.4 out of 10, Exceptional, (13)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
Dugway Hideaway Walking Distance to Lime Rock Park
West Hartford Center Apartment
Fridge, microwave, oven, stovetop

West Hartford Center Apartment

9.6 out of 10, Exceptional, (24)
"The home was very beautiful and very clean. "
West Hartford Center Apartment
West Hartford Center 1st floor
Interior

West Hartford Center 1st floor

8.0 out of 10, Very good, (11)
"Loved the place! Perfect for our family of 4 and very comfortable. "
West Hartford Center 1st floor
Hemlock Hill Suite - 1-bedroom apartment with WiFi, AC in lovely Litchfield
Living area

Hemlock Hill Suite - 1-bedroom apartment with WiFi, AC in lovely Litchfield

Hemlock Hill Suite - 1-bedroom apartment with WiFi, AC in lovely Litchfield
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (21)
"This was a wonderful trip! Absolutely loved the space and location. Loved the walking trail nearby and the little town. Will definitely be back :) "
The price is CA $204
CA $393 total
includes taxes & fees
Aug 31 - Sep 1
River Overlook - Check the view from your deck!
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
Property grounds

The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

9.8 out of 10, Exceptional, (12)
"We enjoyed our stay. The place was very clean and the accommodations were very good. Close to town and there is a brewery/restaurant right down the road if you need to get a bite. We will be back when we visit Connecticut. "
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (28)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Fridge, microwave, oven, stovetop

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

8.8 out of 10, Excellent, (9)
"We were in Connecticut for our nephew's wedding and the house was an excellent alternative to getting hotel rooms. Roomy and comfortable, it made for a great stay and allowed for fun mealtime conversations and visits from local family members."
The price is CA $288
CA $563 total
includes taxes & fees
Sep 13 - Sep 14
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

9.2 out of 10, Wonderful, (42)
"Fantastic hosts and great facilities would highly recommend"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE
Fridge, microwave, stovetop, dishwasher

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

10.0 out of 10, Exceptional, (5)
2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Interior

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice apartment. Beautiful grounds and gardens. We enjoyed ourselves. It was a very comfy place to return to as we enjoyed Jacob's Pillow and our other explorations around the Berkshires. "
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Charming Boutique Studio suite with everything you need for a getaway
Interior

Charming Boutique Studio suite with everything you need for a getaway

10.0 out of 10, Exceptional, (6)
"Had a great time. Ive stayed here multiplt times and keep coming back. Jessica is an amazing host. Very easy to talk to... but they leave you alone. Just an absolutely phenomenal stay"
Charming Boutique Studio suite with everything you need for a getaway
Peaceful Meadow Retreat
Terrace/patio

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (10)
"Quite and very clean"
The price is CA $154
CA $285 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful Meadow Retreat
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
Outdoor dining

The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

9.8 out of 10, Exceptional, (10)
"Very nice, well appointed house across the street from beautiful Highland lake. Great location to explore the northwestern part of the state. Would definitely stay again!"
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
Charming apartment 7 minute walk to downtown
Fridge, microwave, oven, stovetop

Charming apartment 7 minute walk to downtown

10.0 out of 10, Exceptional, (15)
"This place is beautiful and so clean. They thought of everything. Decorated beautifully. I would highly recommend staying here. "
The price is CA $204
CA $366 total
includes taxes & fees
Sep 28 - Sep 29
Charming apartment 7 minute walk to downtown
The Serendipity Spot
Property grounds

The Serendipity Spot

10.0 out of 10, Exceptional, (1)
"Very comfortable, soft bed, cute decor and very convenient location for Great Barrington and surrounding area. Owners are kind, ready to help whenever you need something. Overall this is a great place to stay and we highly recommend it to anyone spending some time in the area. "
The Serendipity Spot
Connecticut Retreat: Steps to Historic Downtown!
Apartment (2 Bedrooms) | Interior

Connecticut Retreat: Steps to Historic Downtown!

3.5 star property
10.0 out of 10, Exceptional, (1)
"Clean and setup for short-term rentals with spare towels, sheets, etc (unlike many other places I've seen)."
Connecticut Retreat: Steps to Historic Downtown!
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

Find out more about Winsted

Find out more about Winsted

Winsted Apartments information

Number of reviews
20
Accommodation
68 Apartments
Lowest Price
CA $154
Highest Price
CA $288

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