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Compare 67 Apartments in Winsted with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (21)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

West Hartford Center Apartment

9.6 out of 10, Exceptional, (19)
"Really enjoyed my stay. The apartment is comfortable and spacious. The property manager was super helpful. I’d happily stay again. "
West Hartford Center Apartment

West Hartford Center 1st floor

8.0 out of 10, Very Good, (8)
"Loved the place! Perfect for our family of 4 and very comfortable. "
West Hartford Center 1st floor

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"very peaceful, amazing view!"
The price is SAR 619
SAR 1,133 total
includes taxes & fees
19 May - 20 May
River Overlook - Check the view from your deck!

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

9.6 out of 10, Exceptional, (10)
"Wonderful property, amazing views. Owners are very helpful and accommodating. Will definitely stay again!"
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

Walk to Memorial Park: Pet-Friendly Bethlehem Home

10.0 out of 10, Exceptional, (6)
"We could not have been more pleased with the property or hosts. The property was clean and looked better in persons. Hosts were very friendly and accommodating. "
Walk to Memorial Park: Pet-Friendly Bethlehem Home

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

9.8 out of 10, Exceptional, (9)
"This property was the perfect place for us. Clean, bright, large rooms, good water pressure in the shower, on the lake. Location location location. The owners have done a very nice job as renters. Congrats to them :)"
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
"Lovely quiet spot with plenty of eating options around the area. Well maintained."
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (56)
"This is such a cute little spot! It is a couple of miles outside the center of town. There is a pizza restaurant and breakfast spot within 50 yards. The hosts were fantastic with communicating in advance of my arrival. "
The price is SAR 563
SAR 953 total
includes taxes & fees
11 May - 12 May
Litchfield Hills Hideaway

Cozy Tree Haus 1 Bedroom Apt

9.4 out of 10, Exceptional, (3)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
The price is SAR 431
SAR 1,145 total
includes taxes & fees
19 May - 20 May
Cozy Tree Haus 1 Bedroom Apt

RIVERSIDE HOMESTEAD on the Farmington River

2.0 star property
9.8 out of 10, Exceptional, (11)
"Clean, quiet, easy to find. Over-garage apartment with good heating and a terrific view of the Farmington River. All amenities provided. Couldn't be happier with my stay!"
The price is SAR 319
SAR 700 total
includes taxes & fees
3 Jun - 4 Jun
RIVERSIDE HOMESTEAD on the Farmington River

Apartment in Gorgeous Stonybrook Farm

9.4 out of 10, Exceptional, (44)
"Our stay was very relaxing and the grounds are beautiful! Very quiet and charming place to stay."
Apartment in Gorgeous Stonybrook Farm

Cozy Modern Farm Haus 2 Bedroom Apartment

10.0 out of 10, Exceptional, (3)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
The price is SAR 591
SAR 1,196 total
includes taxes & fees
12 May - 13 May
Cozy Modern Farm Haus 2 Bedroom Apartment

Steele Brook Manor Tranquil get away nestled in Litchfield County.

2.0 star property
9.4 out of 10, Exceptional, (3)
"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. "
The price is SAR 686
SAR 1,356 total
includes taxes & fees
1 Jun - 2 Jun
Steele Brook Manor Tranquil get away nestled in Litchfield County.

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

9.2 out of 10, Wonderful, (40)
"We enjoyed three nights at this location. Very clean and well decorated little hideaway very private. Any questions were promptly answered we would stay here again!!"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Charming apartment 7 minute walk to downtown

10.0 out of 10, Exceptional, (11)
"Lovely very comfortable and up to date apartment! Highly recommend -hosts very responsive and helpful! "
The price is SAR 555
SAR 991 total
includes taxes & fees
9 May - 10 May
Charming apartment 7 minute walk to downtown

Charming 2-bedroom apartment with AC, WiFi in welcoming Westfield

9.0 out of 10, Wonderful, (2)
"Very clean and quiet "
Charming 2-bedroom apartment with AC, WiFi in welcoming Westfield

Charming Boutique Studio suite with everything you need for a getaway

10.0 out of 10, Exceptional, (3)
"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

2.0 star property
10.0 out of 10, Exceptional, (9)
"The place is beautiful and very quiet and relaxing"
Peaceful Meadow Retreat
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

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

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

10.0 out of 10, Exceptional, (5)
"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

Lakefront Spring Stunner in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (68)
"Overall a nice place to visit. A small family who likes the outdoors would enjoy it. "
Lakefront Spring Stunner in New England Just 2 Hours From NYC
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

What's it like to stay at an apartment in Winsted?
You’ll find 5 apartments to choose from in Winsted for your trip.
Why choose an apartment over a traditional hotel room?
Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples who want to stay away from the tourist areas.
What's the top apartment I should consider for a stay in Winsted?
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: Includes free WiFi, private patios, and private yards. The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock: Free WiFi, private patios, and separate dining areas are included. Access to onsite laundry facilities is available on site.
How many apartments will I be able to find in Winsted?
Expedia has 5 apartments to book in Winsted.
What can I expect from the weather during my trip to Winsted?
Though weather is just one factor, it can really affect your travel plans, especially when you’re planning an extended stay in Winsted. 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 should I see in Winsted?
Highland Lake and Rowley Fields are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. Platt Hill State Park and Burr Pond State Park are other places to visit while you’re in town.
What's the best way to get to and around Winsted?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Bradley Intl. Airport (BDL), which is located 19.3 mi (31 km) from the heart of the city. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 24.5 mi (39.4 km) away. If you’d like to explore around the area, you may want a rental car for your journey.