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Winsted Holiday Homes

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    1 / 21
    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 30 kilometres of Winsted, Connecticut.

    1 / 37
    5 of 5 bubbles (1) Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 12
    5 of 5 bubbles (3) Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 27
    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • Balcony
    • Grill
    • Terrace
    • Housekeeping...
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Judd Farm House is situated on 33 acres, the house is in farm country. It is surrounded by rolling hills of Litchfield. There are country roads for walking and biking with very little traffic. It is a perfect retreat for a group there are generous size bedrooms tastlefully decorated. There is a... View all property information
    Location Information
    Bethlehem, Connecticut 06795
    1 / 16
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Bethlehem, Connecticut 06751
    1 / 21
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Prana Residence-Spa creates an environment for relaxation and the rejuvenation of vital life (prana). If you appreciate tranquility in the pursuit of personal happiness and are inspired by unique surroundings, personal spa facilities and select services, Prana Residence-Spa is waiting for you.... View all property information
    Location Information
    Cornwall Bridge, Connecticut 06754
    1 / 37
    Morris
    3 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Direct waterfront house with private sandy beach located on the West shoreline of Bantam Lake. Contemporarty A frame style house with 3 bedrooms - 2.5 baths and cozy loft area. All amenities. View all property information
    Location Information
    Morris, Connecticut 06763
    1 / 13
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    West Cornwall, Connecticut 06796
    1 / 15
    Bethlehem
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come in, freshen up and enjoy the complimentary snacks and beverages waiting for you in this spacious vaulted ceiling queen bed guest rental in Bethlehem, Connecticut. Our private top floor guest suite is fully equipped for comfort and easy on the budget. The things that are important to you are... View all property information
    Location Information
    Bethlehem, Connecticut 06751
    1 / 13
    Granville, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    • Housekeeping...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the... View all property information
    Location Information
    Granville, Berkshires 01034
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    1 / 14
    Bethlehem
    Private Room, Sleeps 10 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Bethlehem, Connecticut 06751
    1 / 17
    4 of 5 bubbles (1) Very good
    Goshen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Goshen, Connecticut 06756
    1 / 21
    5 of 5 bubbles (1) Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this... View all property information
    Location Information
    New Preston, Connecticut 06777
    5 of 5 bubbles 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...
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    1 / 13
    Bloomfield
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Air Conditioning
    • Private Outdoor...
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    • Satellite TV
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    BEAUTIFUL 100% NEWLY renovated Victorian Mansion, on 3.5 acre private ESTATE., directly alongside the ELEGANT greens and fairways of the prestigious private TUMBLE BROOK COUNTRY CLUB. LARGE INGROUND SWIMMING POOL. Great GOLF COURSE views from every window. PRIVATE- AWAY FROM THE ROADS- Large,... View all property information
    Location Information
    Bloomfield, Connecticut 06002
    1 / 11
    5 of 5 bubbles (1) Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Parking
    • Satellite TV
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area.... View all property information
    Location Information
    Falls Village, Connecticut 06031
    5 of 5 bubbles Reviewed 18 September 2016
    I only wish my mobility was better to take a walk on this beautiful property very close to Lime Rock Park and many other cultural attractions. Owners were very nice and obviously...
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    1 / 42
    5 of 5 bubbles (3) Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Porch
    • Washer
    • Satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This newly renovated 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. This house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove which offers many recreational... View all property information
    Location Information
    Lakeville, Connecticut 06068
    5 of 5 bubbles Reviewed 27 May 2014
    My friends and I stayed at this house for a race weekend at Lime Rock Park. The location of this house is perfect - 15 minutes from the track, walking distance from a small lake...
    5 of 5 bubbles Reviewed 7 May 2014
    We rented this sweet home in Lakeville for the bride and bridesmaids for my son's wedding. The bridal party came from far and wide and this was the perfect destination for the...
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    1 / 24
    4.5 of 5 bubbles (3) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Furnished cottage, with large deck, on 4 acres of woods, with brook and 200 feet Housatonic River frontage. Use of Sharon beach, tennis courts, and children's play area. The brook will dry up during summer dry spells. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from... View all property information
    Location Information
    West Cornwall, Connecticut 06796
    5 of 5 bubbles Reviewed 18 August 2015
    Really enjoyed staying here with y sister and partner and my family (three young kids), who played endlessly in the stream which was full of frogs and stones. We could relax from...
    4 of 5 bubbles 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...
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    1 / 15
    Barkhamsted
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Barkhamsted, Connecticut 06063
    1 / 24
    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Central Heating
    • Internet Access
    • Waterfront
    • Porch
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Visit the beautiful shores of Lake Waramaug in this charming 3-bedroom, 2-bathroom New Preston vacation rental cottage that comfortably sleeps 6 with room for up to 8. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and 22 foot dock.... View all property information
    Location Information
    New Preston, Connecticut 06777
    1 / 32
    Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Indoor Pool
    • Mountain Views
    • DVD Player
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience pure relaxation and tranquility when you escape to ‘Prana Residence-Spa,’ a 3-bedroom, 3-bathroom vacation rental house on five and a half acres of Cornwall Bridge's beautiful woodlands! Featuring accommodations for up to 7, along with exclusive use of an indoor pool, sauna, hot tub, and... View all property information
    Location Information
    Cornwall, Connecticut 06754
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    1 / 11
    5 of 5 bubbles (18) Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Balcony
    • Grill
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Falls Village, Connecticut 06031
    4 of 5 bubbles Reviewed 15 September 2016
    Enjoyed our stay at this beautiful, well appointed cottage and would book again. Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
    5 of 5 bubbles Reviewed 4 September 2016
    We spent a very relaxing weekend here and took great advantage of the deck overlooking the river. Everything was as described and depicted in photos. It was awesome to hear the...
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    1 / 23
    Lakeville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    -Available Christmas and New Years -3 Ski Mountains nearby. Mohawk, Butternut, Catamount. Just steps to everything in town! Or grab a tall glass of Lemonade and a good book & relax on the porch. This petite in-town home is convenient to restaurants, shops, & Lake. The perfect spot to getaway &... View all property information
    Location Information
    Lakeville, Connecticut 06039
    1 / 25
    Warren
    7 Bedrooms, 8 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ** Please note that this property can be rented in conjunction with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional information ** If you’re searching for the perfect place to stay for your next family gathering, “Carriage House” is just the spot for... View all property information
    Location Information
    Warren, Connecticut 06777
    1 / 25
    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Set on the edge of a valley with westerly views on a beautiful street in Litchfield this vintage home has all modern amenities and style. Has a well in the mudroom and the steep staircase to give you a really authentic 1820's retreat. A large park-like yard with old granite barn foundations and... View all property information
    Location Information
    Litchfield, Connecticut 06759
    1 / 24
    New Marlborough, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Waterfront
    • Mountain Views
    • Parking
    • DVD Player
    • Central Heating
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough, within the Berkshires, serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and room to comfortably sleep 4 guests, this property is an excellent choice for people who are looking for either a... View all property information
    Location Information
    New Marlborough, Berkshires 01230
    1 / 4
    Torrington
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Waterfront
    • Skiing: Property Is...
    • Hot Tub
    • Housekeeping...
    • DVD Player
    • Mountain Views
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in rural Winchester/Torrington area, this gated property is easy to get to, located on 200 acres of wooded land. It is used primarily as a resort, due to all its amenities, including, Indoor / Outdoor pools, hot tub, exercise room, sauna, indoor/outdoor tennis. It has its own spring fed... View all property information
    Location Information
    Torrington, Connecticut 06790
    1 / 10
    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream.... View all property information
    Location Information
    New Marlborough, Berkshires 01230