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Compare 51 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

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park

9.0 out of 10, Wonderful, (9)
"Great location and super easy to navigate!"
The price is AED 735
AED 1,157 total
includes taxes & fees
24 Nov - 25 Nov
Dugway Hideaway Walking Distance to Lime Rock Park
RIVERSIDE HOMESTEAD on the Farmington River
Room

RIVERSIDE HOMESTEAD on the Farmington River

2.0 star property
9.6 out of 10, Exceptional, (10)
"clean,quiet, and peaceful.slept well. coffee was great.Thank you so much . "
The price is AED 312
AED 686 total
includes taxes & fees
1 Dec - 2 Dec
RIVERSIDE HOMESTEAD on the Farmington River
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, (37)
"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.
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...
River Overlook - Check the view from your deck!
Litchfield Hills Hideaway
Living area

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (54)
"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 AED 551
AED 951 total
includes taxes & fees
27 Nov - 28 Nov
Litchfield Hills Hideaway
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Room

TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX

9.8 out of 10, Exceptional, (18)
"My stay here was amazing.Very clean.Very welcoming with a forever homely feel.The communication with the property owner/manager was great and very helpful with everything.When i return to Connecticut,I will be looking forward to returning to this rental and also recommending to family and friends if traveling to the area.5*"
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*

8.0 out of 10, Very Good, (1)
"Check in was easy. Communication with host was swift. Great Bed. Pretty basic amenities. Would definitely rent from them again. "
The price is AED 320
AED 819 total
includes taxes & fees
24 Nov - 25 Nov
#2 *Beautiful 1 BR Apartment - Central CT*
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Exterior

The Overlook near South Farms in Litchfield County is Hospitality, integrated.

9.2 out of 10, Wonderful, (5)
"This apartment is beautiful and clean. The bed provided a wonderful nights sleep. We stayed during foliage season and the area is absolutely gorgeous. There is ample parking for your car, a separate private entrance, a shared back deck. The hostess left us a bottle of wine and there was coffee and fresh cream, spring water and eggs in the fridge, a nice touch. There’s a gas station close by with a convenience store and a burrito truck open into the evening hours. Also,there’s a beer and wine...
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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, (2)
"The apartment was so charming, clean and comfortable! It was larger than it looks on line. Location was fantastic. Check out the "King's boards" on the floor - incredible! We will definitely stay again if in the area.fantastic. "
Walk to Memorial Park: Pet-Friendly Bethlehem Home
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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!
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
West Hartford Center Apartment
Living area

West Hartford Center Apartment

9.8 out of 10, Exceptional, (16)
"Super clean place. Quiet. Easily accessible to local places. Really loved all of the windows and views of the neighborhood. Thank you for sharing your sweet space!!! "
West Hartford Center Apartment
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
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
House and waterfront yard with dock

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

9.8 out of 10, Exceptional, (9)
"Perfect for our visit to our children and grand children. The lake is across the street with the marina next door. Rented a pontoon boat, at a discounted rate for beautiful day with the kids. Minor problem getting in initially, but resolved by Jeanne quickly. Note that this is a renovated lake residence which has a second story rental which can get a bit noisy and the bathroom is in the rear of the house with the bedroom in the front. Overall will be returning in the future."
The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

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

8.6 out of 10, Excellent, (4)
"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 AED 540
AED 1,168 total
includes taxes & fees
4 Dec - 5 Dec
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Room

Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

10.0 out of 10, Exceptional, (3)
"Beautiful, clean simple place. Convenient to Great Barrington and all the wonderfulness of the Berkshires. We would happily return"
Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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 AED 573
AED 977 total
includes taxes & fees
24 Nov - 25 Nov
Charming apartment 7 minute walk to downtown
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
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

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, (37)
"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.
Family House On Highland Lake with Dock
Front of home

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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?
There are 17 hotels and other accommodations in Winsted. Though there aren’t many apartments, we can help you search for similar accommodations. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. Even filter by similar property types like condos, vacation homes, or cottages.
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?
Enjoy a restful stay with fast internet, smart TV and the company of your pet.: Includes free WiFi, fireplaces, and Smart TVs. The Inn at Highland Lake, 2nd Floor, waterfront yard with a boat dock: Free WiFi, private patios, and private yards are included. Access to a fitness center is available on site. The Inn at Highland Lake, 1st Floor, waterfront yard with a boat dock: Includes free WiFi, private patios, and separate dining areas.
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.