We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Winsted, CT and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
All 22 Rentals in the Winsted Area
loading...
Sort by

The following rentals are within 30 kilometres of Winsted, Connecticut.

From
$320
Per Night
View Details
1 / 19
Payment Protection
Lakeville
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Reviews (3) Make Enquiry
From
$192
Per Night
View Details
1 / 37
Payment Protection
Salisbury
Cottage - 
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
From
$256
Per Night
View Details
1 / 15
Payment Protection
Sharon
Cottage - 
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (3) Make Enquiry
From
$81
Per Night
View Details
1 / 20
Payment Protection
New Preston
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $5,000 per month July $5,000 per month Aug $6,000 per month Memorial Day to Labor Day $12,000 Enjoy this green woodsy retreat in beautiful Litchfield County and relax in a charming farmhouse that is spacious... View all property information
Make Enquiry
5 of 5 stars Reviewed 8 July 2014
We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
See all reviews
From
$183
Per Night
View Details
1 / 15
Payment Protection
Sandisfield, MA
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
Make Enquiry
5 of 5 stars Reviewed 2 February 2015
We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
See all reviews
From
$256
Per Night
View Details
1 / 11
Falls Village
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (13) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 February 2015
Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep...
5 of 5 stars Reviewed 19 January 2015
Perfect getaway location with all the amenities – including a fireplace for a perfect winter stay. The cottage was clean and inviting, and the character of the furnishings and...
See all reviews
From
$1,406
Per Week
View Details
1 / 17
Payment Protection
Goshen
House Rental - 
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in the heart of northwestern Connecticut's elegant Litchfield County. The house is a fully furnished, newly constructed 5 bedroom / 4 bathroom home complete with a beautiful kitchen, fireplace, deck, state-of-the-art home theater system and all the amenities of Woodridge Lake. You will... View all property information
Make Enquiry
From
$192
Per Night
View Details
1 / 22
West Cornwall
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Winter activities: The cottage is 10 minutes from the Mohawk Mountain Ski Area - 5 trails, 4 lifts and $30 lift tickets; and 45 minutes from Butternut Basin in Great Barrington, MA, and Catamount Ski Area in Hillsdale, NY. Other nearby winter activity includes: walking along Upper River Road... View all property information
Make Enquiry
4 of 5 stars Reviewed 30 January 2015
This was a wonderful cabin, no bells or whistles, but all of the amenities. It was comfortable clean and very spacious. The floor plan lends itself to lots of nooks and crannies...
See all reviews
From
$320
Per Night
View Details
1 / 5
Payment Protection
Granville, MA
Chalet - 
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The house has a unique setting in the heart of a nature... View all property information
Make Enquiry
From
$384
Per Night
View Details
1 / 10
Payment Protection
Norfolk
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This newly renovated 1850's farmhouse in charming, rural Northwest CT has warmth and privacy galore! The home is located on eight acres of land on a dead end road, but is only 4 miles from the center of town! There are three bedrooms, a laundry closet, and 2 full baths upstairs. A jacuzzi... View all property information
Make Enquiry
Get the List
From
$479
Per Night
View Details
1 / 13
Payment Protection
West Cornwall
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Architect-designed, contemporary, 3-bedroom country home. Sited on five private hillside acres with breathtaking views of the Housatonic River Valley in the foothills of the Berkshire Mountains. With geothermal heating and air conditioning, heated floors, wood, slate, and stone flooring, gourmet... View all property information
Make Enquiry
From
$64
Per Night
View Details
1 / 15
Payment Protection
Plymouth
House Rental - 
8 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This beatuiful 8 room Raised Ranch is located on a quiet dead end street. Home is very spacious with a new efficient oil based heating system. Large eat in kitchen with appliances. Large dining room with sliders to two tier deck overlooking a 1 acre lot. Living room is large with fireplace.... View all property information
Make Enquiry
From
$192
Per Night
View Details
1 / 1
Payment Protection
Goshen
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Reserve your get-away for 2014 at the best lake resort community in NW Connecticut, Woodridge Lake ! This property books quickly and far in advance during the summer season and is very popular with families ! We are offering as a seasonal monthly rental this 3 bedroom 2 bath home nestled in the... View all property information
Make Enquiry
From
$115
Per Night
View Details
1 / 8
Payment Protection
Torrington
Apartment - 
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Enquiry
Amenities & Details
  • Balcony
  • Internet Access
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Large apartment, windows on 3 sides, new appliances, Wi-Fi, Conveniently situated on Main street downtown Torrington, from one to ten minutes away from restaurants, ten minutes away from movies theater, ten minutes away from the Post office, and all this is walking time to these locations, one... View all property information
Make Enquiry
From
$384
Per Night
View Details
1 / 16
Payment Protection
Bethlehem
House Rental - 
6 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All... View all property information
Make Enquiry
From
$377
Per Night
View Details
1 / 20
Payment Protection
New Hartford
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Come enjoy a stay in this newly remodeled waterfront property on West Hill Lake in Litchfield County. Located on 4+ acres, 3 wooded, this 4bed/3bath 2600+ square foot home can comfortably accommodate up to 8 guests. Beautifully appointed, the features include; wood burning fireplace, marble... View all property information
Make Enquiry
From
$639
Per Night
View Details
1 / 18
Payment Protection
Litchfield
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Our home is on Woodridge Lake, a private lake community in the town of Goshen in Litchfield County CT. The house is walking distance (about 200 yards) to the clubhouse area which includes 8 tennis courts, a pool (summer), beach, basketball court, fitness center, snack bar (summer). **We are... View all property information
Make Enquiry
From
$1,278
Per Night
View Details
1 / 3
Farmington
House Rental - 
6 Bedrooms, 8 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, weekly or long term stay. . 6 bedrooms, 7.5 baths, swimming pool,... View all property information
Make Enquiry
From
$83
Per Night
View Details
1 / 7
Payment Protection
Bristol
Apartment - 
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Located in 1880 home in older quiet neighborhood .Nearby park to walk in. Located 2 miles from ESPN and the great Lake Compounce amusement park. Walking distance to clock museum, shopping, library and churches. Short drive to carousel museum. 13 miles from capital of Hartford. Off street... View all property information
Make Enquiry
From
$320
Per Night
View Details
1 / 14
Payment Protection
New Preston
Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
'Little Wheel' is the guest cottage on the historic Riverdance MIll property (circa 1875) in the charming village of New Preston, CT. The cottage has been totally reconstructed recently. It is bright and airy in the Spring and Summer, cozy and warm in the Fall and Winter and ALWAYS romantic! The... View all property information
Make Enquiry
From
$505
Per Night
View Details
1 / 15
Payment Protection
Barkhamsted
Cabin - 
6 Bedrooms, 8 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,... View all property information
Make Enquiry
Enquire for rates
1 / 20
Payment Protection
Litchfield
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Garden
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Prana Residence-Spa creates an environment for relaxation and the rejuvenation. If you appreciate tranquility in the pursuit of personal happiness, are inspired by nature and are in need of personal spa facilities, Prana Residence-Spa is waiting for you. Prana Residence-Spa sits in a most tranquil... View all property information
Make Enquiry
Go to map view
Book Online(18)
Use filters to find the best results!

Suitability

  • Wheelchair access (2)
  • Elder access (6)
  • Suitable for children (2)
  • Pet friendly (5)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (19)
  • Internet (18)
  • Grill (15)
  • Parking (14)
  • Air Conditioning (13)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities