Photo by Kim Knox Beckius

Apartments in Winsted for Rent

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Apartments in Winsted

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (32)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

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

West Hartford Center Apartment

9.6 out of 10, Exceptional, (24)
"We enjoyed our stay. Beautiful house, near downtown and quiet. Thank you for having us"
West Hartford Center Apartment

Dugway Hideaway Walking Distance to Lime Rock Park

9.4 out of 10, Exceptional, (14)
"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

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (23)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
The price is ¥21,966
¥42,309 total
includes taxes & fees
Oct 2 - Oct 3
River Overlook - Check the view from your deck!

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

8.8 out of 10, Excellent, (10)
"We enjoyed staying here. Great place, good communication, and a good rate for the space."
The price is ¥18,483
¥43,739 total
includes taxes & fees
Oct 9 - Oct 10
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

Charming Boutique Studio suite with everything you need for a getaway

10.0 out of 10, Exceptional, (7)
"Convenient location, clean and cool interior, wonderful experience with privacy, room amenities, and polite/efficient owners. Will use again and will recommend to others. "
Charming Boutique Studio suite with everything you need for a getaway

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

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (63)
"Excellent- great location, great value, clean, comfortable, owners are great people"
Litchfield Hills Hideaway

Renovated Apartment on Main St.

7.4 out of 10, Good, (3)
"Great spot right in town."
Renovated Apartment on Main St.

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.

2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

10.0 out of 10, Exceptional, (6)
"Quick weekend visit to family in CT. Clean apartment. Off street parking. "
2 BEDROOM APARTMENT IN BRISTOL NEAR PLAINVILLE

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

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

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

The Jefferson Guest House, Spacious, Special Views

10.0 out of 10, Exceptional, (7)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
The price is ¥36,980
¥48,666 total
includes taxes & fees
Oct 12 - Oct 13
The Jefferson Guest House, Spacious, Special Views

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

9.6 out of 10, Exceptional, (15)
"Was a Great stay. The house was beautiful, even better than the pictures. Very well furnished. Would definitely recommend."
The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock

Charming apartment 7 minute walk to downtown

10.0 out of 10, Exceptional, (15)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
The price is ¥22,928
¥40,715 total
includes taxes & fees
Oct 27 - Oct 28
Charming apartment 7 minute walk to downtown

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (11)
"Quite and very clean"
The price is ¥18,342
¥32,557 total
includes taxes & fees
Oct 20 - Oct 21
Peaceful Meadow Retreat

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

9.2 out of 10, Wonderful, (44)
"Fantastic hosts and great facilities would highly recommend"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

9.6 out of 10, Exceptional, (4)
"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 ¥13,165
¥40,759 total
includes taxes & fees
Oct 6 - Oct 7
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winsted Hotel Reviews

Find out more about Winsted

Find out more about Winsted

Winsted Apartments information

Number of reviews
290
Accommodation
62 Apartments
Lowest Price
¥32,557
Highest Price
¥48,666

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, 1st Floor, waterfront yard with a boat dock: Includes free WiFi, private patios, and separate dining areas. Access to onsite laundry facilities is available on site. The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: Free WiFi, private patios, and private yards are included. Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Includes free WiFi, fireplaces, 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 Rowley Fields are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. Burr Pond State Park and Winchester Historical Society 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.