Photo by Kim Knox Beckius

Search Apartments in Winsted

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 56 Apartments in Winsted with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (13)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
RIVERSIDE HOMESTEAD on the Farmington River
Room

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!"
RIVERSIDE HOMESTEAD on the Farmington River
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
living area open to kitchen

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
River Overlook - Check the view from your deck!
Property grounds

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
The price is SAR 563
SAR 1,075 total
includes taxes & fees
18 Feb - 19 Feb
River Overlook - Check the view from your deck!
West Hartford Center Apartment
Living area

West Hartford Center Apartment

9.6 out of 10, Exceptional, (19)
"Location was perfect for our needs. Property amenities were adequate."
West Hartford Center Apartment
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Room

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

9.2 out of 10, Wonderful, (38)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Litchfield Hills Hideaway
Living area

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is SAR 563
SAR 956 total
includes taxes & fees
21 Feb - 22 Feb
Litchfield Hills Hideaway
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
House and waterfront yard with dock

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

9.6 out of 10, Exceptional, (8)
"We had a great time at Highland Lake. The apartment was so comfortable, and larger than I would have thought from the description. It was convenient to town - the teens loved access to DQ, pizza shops, etc just a few minutes away. There were kayaks and a paddleboat we could borrow, which I somehow missed in the description - nice pluses! The lake access from the dock was perfect. We brought stand-up paddleboards, and had an easy time launching them and exploring the lake. In the apartment,...
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock
Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park

9.2 out of 10, Wonderful, (11)
"My partner and I stayed here overnight for a nearby wedding in Salisbury. The property was easy to find and conveniently located near main roads for the area. The hosts are very receptive to questions and general communications as well!"
Dugway Hideaway Walking Distance to Lime Rock Park
Peaceful Meadow Retreat
Property grounds

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (8)
"As usual very nice stay on property! Would recommend to everyone. Spacious, clean and quiet location!"
The price is SAR 308
SAR 644 total
includes taxes & fees
18 Feb - 19 Feb
Peaceful Meadow Retreat
Cozy Tree Haus 1 Bedroom Apt
Livingroom

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 1,097 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Tree Haus 1 Bedroom Apt
Apartment in Gorgeous Stonybrook Farm

Apartment in Gorgeous Stonybrook Farm

9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm
Walk to Memorial Park: Pet-Friendly Bethlehem Home
Bethlehem Vacation Rental | 1BR | 1BA | Step Required | 1,380 Sq Ft

Walk to Memorial Park: Pet-Friendly Bethlehem Home

10.0 out of 10, Exceptional, (3)
"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
West Hartford Center 1st floor
Dining

West Hartford Center 1st floor

8.0 out of 10, Very Good, (8)
"Worked great for our visit. Very spacious. "
West Hartford Center 1st floor
Charming apartment 7 minute walk to downtown
Entrance to living room.

Charming apartment 7 minute walk to downtown

10.0 out of 10, Exceptional, (8)
"Lovely very comfortable and up to date apartment! Highly recommend -hosts very responsive and helpful! "
The price is SAR 593
SAR 995 total
includes taxes & fees
21 Feb - 22 Feb
Charming apartment 7 minute walk to downtown
Steele Brook Manor Tranquil get away nestled in Litchfield County.
Living area

Steele Brook Manor Tranquil get away nestled in Litchfield County.

2.0 star property
10.0 out of 10, Exceptional, (1)
"House was located in a quiet neighborhood. The gardens on the grounds were beautiful. Allison suggested a scenic drive which we took to see the fall foliage. 6 of us and we had the best time!"
The price is SAR 615
SAR 1,259 total
includes taxes & fees
23 Feb - 24 Feb
Steele Brook Manor Tranquil get away nestled in Litchfield County.
Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE
Living area

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE
1 bedroom in a factory converted loft, with fitness room, WiFi in Torrington
Living area

1 bedroom in a factory converted loft, with fitness room, WiFi in Torrington

1 bedroom in a factory converted loft, with fitness room, WiFi in Torrington
Charming Boutique Studio suite with everything you need for a getaway
Living area

Charming Boutique Studio suite with everything you need for a getaway

10.0 out of 10, Exceptional, (1)
"This was perfect for our golf weekend getaway. It had everything we needed and was decorated very nice !! Nice neighborhood and the hosts gave us privacy. It doesn’t have a full kitchen but we didn’t want one ( it’s vacation and was too hot . lol ) and we ordered out anyway. I loved having the Kuriegg and i didn’t have to bring my own .. just be careful when using it for some reason it had a mind of its own 🤗. I would stay here again if we are ever in the area. Also the bed was very comfortable"
Charming Boutique Studio suite with everything you need for a getaway
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.
Don't see what you're looking for?
See all available properties in Winsted
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winsted

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

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

10.0 out of 10, Exceptional, (91)
"The house exceeded all out expectations. Beautiful, convenient to services, stunning location on the lake, plenty of off street parking. The host and I spoke multiple times throughout the stay regarding small things like trash and recycling expectations, etc."
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (22)
"Mariana is a wonderful host. She communicates well and is very efficient in responding to any questions or inquiries you may have.The cabin is very clean, and has just about everything you would need. We really enjoyed using the fireplace! 10/10 recommend. "
Cozy & Chic Cabin by the Lake, with access to private Beach!
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?
Listed below are some of the favorite apartments in the area: The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: Includes free WiFi, private patios, and private yards. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 24.4 mi/39.3 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. River Overlook - Check the view from your deck!: It’s situated in Canton, 10.4 mi/16.7 km away. Includes private patios and Smart TVs. Litchfield Hills Hideaway: 15.3 mi/24.7 km away in Litchfield. Amenities include private patios. West Hartford Center Apartment: It’s located in West Hartford, 19.9 mi/32 km from Winsted. Includes private balconies, jetted bathtubs, and Smart TVs.
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 Burr Pond State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. Winchester Historical Society and Platt Hill 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.