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 Rentals and Homes in South Kent, CT

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price range
    (€286 Average)
    €0per night €1,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...

    The following rentals are within 25 kilometers of South Kent, Connecticut.

    From
    €266
    / Night
    Payment Protection
    View Details
    1 / 21
    5 of 5 stars (1) Excellent
    New Preston
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    From
    €333
    / Night
    Payment Protection
    View Details
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    From
    €555
    / Night
    Payment Protection
    View Details
    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11
    Overview Make Enquiry
    Overview
    From
    €1,065
    / Week
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (1) Excellent
    New Milford
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • TV
    • Washer
    • Water Views
    • Fireplace
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    You will enjoy a very charming home with a rustic atmosphere. Swim and enjoy beautiful Candlewood Lake on a private beach, explore Litchfield Hills with true New England charm, sit on the patio or veranda to soak in the sun, and gather around the fireplace in the evening. The house is perfect for... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776
    From
    €666
    / Night
    Payment Protection
    View Details
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
    Make Enquiry
    Location Information
    Cornwall Bridge, Connecticut 06754
    From
    €257
    / Night
    Payment Protection
    View Details
    1 / 29
    5 of 5 stars (4) Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • DVD Player
    • Stereo System
    • Deck
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776
    5 of 5 stars Reviewed 27 June 2015
    When reminiscing about our amazing holiday a couple of years ago, we realised we hadn't left a (now long overdue) review for this fantastic property. The pool is great, the house...
    5 of 5 stars Reviewed 10 August 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    See all reviews
    From
    €173
    / Night
    Payment Protection
    View Details
    1 / 51
    5 of 5 stars (1) Excellent
    Pawling, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • TV
    • Air Conditioning
    • Wi-Fi
    • Dryer
    • Grill
    • Patio
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Historic beauty built in 1900 in the heart of the village Town of Pawling only a 90 min metro north train ride from Manhattan and no need for a car you can walk to the house and to most things or take a local taxi if needed for places outside of the village. .. Short walk to Metro North train(2... View all property information
    Make Enquiry
    Location Information
    Pawling, New York 12564
    5 of 5 stars Reviewed 18 August 2015
    We loved our stay at this house. It was very well equipped, the kitchen, bedrooms and living room. It was what we have hoped for it to be. The location is easy to find although we...
    See all reviews
    From
    €178
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (3) Excellent
    Sharon
    3 Bedrooms, 1 Bathroom, Sleeps 5
    other traveller has booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • TV
    • Fireplace
    • Playground
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Want to get away from it all? Just 2 hours away from New York City or Take Metro North and hop in a cab. This house is the perfect getaway located in Sharon, Litchfield County, Connecticut which is in the foothills of the Berkshires. Sharon is the quintessential New England small town. Quiet and... View all property information
    Make Enquiry
    Location Information
    Sharon, Connecticut 06069
    From
    €799
    / Night
    Payment Protection
    View Details
    Bethlehem
    6 Bedrooms, 4 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Private Tennis Court
    • Fireplace
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Bethlehem, Connecticut 06751
    From
    €666
    / Night
    Payment Protection
    View Details
    1 / 8
    5 of 5 stars (2) Excellent
    Millbrook, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 10
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Fireplace
    • Refrigerator
    • Dryer
    • Cooker
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Idle Hour Farm is located in the heart of Hunt Country, Dutchess County NY. It is a peaceful place among rolling hills, horse farms and dairy farms. It is conveniently located 1 1/2 hours from NYC, 1 hour from the Catskill Mountains, 4 hours from the Adirondack Mountains. It is situated on 16... View all property information
    Make Enquiry
    Location Information
    Millbrook, New York 12545
    5 of 5 stars Reviewed 1 March 2015
    If you want a taste of the old with modern conveniences, this spacious farmhouse is for you. Ten of us stayed here comfortably. Don't expect good internet in all parts of the...
    5 of 5 stars Reviewed 10 September 2014
    The house is beautifully furnished, the grounds are lovely, we had a most wonderful stay. We swam in the pond which is a perfect temperature and has a small sandy 'beach' making...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €222
    / Night
    Payment Protection
    View Details
    New Preston
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Fireplace
    • Waterfront
    • Internet Access
    • Patio
    • Satellite TV
    • Water Views
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    New Preston, Connecticut 06777
    From
    €244
    / Night
    Payment Protection
    View Details
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • DVD Player
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    • Housekeeping...
    • Mountain Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nature Lovers Paradise! Light filled, private and peaceful location with fantastic mountain views! Unique seven and a half acre property, with various flowering trees and shrubs. A different scent for different seasons! ***Note: There is also a two bedroom apartment available at same location!****... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776
    From
    €178
    / Night
    Payment Protection
    View Details
    New Milford
    3 Bedrooms, 3 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • DVD Player
    • Fireplace
    • Central Heating
    • Washer
    • Wi-Fi
    • Water Views
    • Pool Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This warm and cozy country lake house provides a comfortable stay in an attractive, rustic atmosphere with lovely scenic views. Located on a quiet road in a friendly community with easy access to a variety of shops and the quaint, historic town of New Milford. Town offers charming colonial... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776
    From
    €25,299
    / Month
    Payment Protection
    View Details
    New Fairfield
    5 Bedrooms, 6 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    There's not much better than summertime on Candlewood Lake! Enjoy all the summer offers in New England from this magnificent waterfront home on Connecticut's largest lake. This architectural designed home is perfect for guests and ALL 5 bedrooms are en-suite! There's a living room with a massive... View all property information
    Make Enquiry
    Location Information
    New Fairfield, Connecticut 06812
    From
    €222
    / Night
    View Details
    1 / 20
    4.5 of 5 stars (7) Very good
    Holmes, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10
    Overview Reviews (7) Make Enquiry
    Overview Reviews (7)
    Amenities & Details
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Private Fishing...
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fully furnished gorgeous home directly on beautiful Whaley Lake only 1-1½ hours from New York City. Two levels each with full kitchen and bath. Washer & dryer, wireless internet, plenty of parking. The units can be rented separately or together. Lower level with huge panoramic windows overlooking... View all property information
    Make Enquiry
    Location Information
    Holmes, New York 12531
    4 of 5 stars Reviewed 20 August 2015
    We spent 4 days on this property and we enjoyed every moment of it. We were four adults and we love fishing and swimming. We booked this property mainly for these things and we...
    4 of 5 stars Reviewed 6 July 2014
    We stayed at Lake Bliss with friends in May, close proximity to hiking, relaxing breakfasts by the lake, nice to have a canoe available, everything we needed was there. Made for a...
    See all reviews
    From
    €200
    / Night
    View Details
    1 / 23
    4 of 5 stars (1) Very good
    Millbrook, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 2
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Internet Access
    • Refrigerator
    • Deck
    • Mountain Views
    • Soap/Shampoo...
    • Air Conditioning
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Castle , Wing's Castle is a true Hudson Valley stone castle Sweeping views of the entire Mid-Hudson Valley, on the High hills of Dutchess county New York. 75 miles north of New York City and 75 miles south of Albany. Rooms are a Dungeon and a Tower room for now. We also have a Fairy Tale Cottage... View all property information
    Make Enquiry
    Location Information
    Millbrook, New York 12545
    4 of 5 stars Reviewed 7 January 2014
    My boyfriend and I went to Wing's Castle for New Year's Eve...and we had a nice, relaxing time. We were looking for no tv's...no outside world..no drama. It was very peaceful...
    See all reviews
    From
    €178
    / Night
    View Details
    1 / 22
    Kent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Cooker
    • Internet Access
    • Patio
    • Air Conditioning
    • Washer
    • Dryer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled in the heart of the village, this private get-away awaits you. Relax and still be in the center of everything. 2 bedrooms, 1 1/2 baths and charming backyard. There is wifi, fully equipped kitchen and a washer dryer. Off street parking. You can walk to 4 restaurants, 2 bakeries and many... View all property information
    Make Enquiry
    Location Information
    Kent, Connecticut 06757
    From
    €241
    / Night
    View Details
    1 / 28
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Deck
    • Satellite TV
    • Fireplace
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SUMMER RENTAL LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful , very private country setting; four bedrooms, large family room with cathedral ceilings; grand piano. All amenities:cable TV, CD, DVD,VCR, internet. All rooms are with AC. Deck by the house with screen house and gas... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776
    From
    €133
    / Night
    View Details
    1 / 22
    4.5 of 5 stars (2) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Dryer
    • Refrigerator
    • Satellite TV
    • Deck
    • Stereo System
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from West Cornwall and its covered bridge,10 minutes from... View all property information
    Make Enquiry
    Location Information
    West Cornwall, Connecticut 06796
    5 of 5 stars 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 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
    €178
    / Night
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    Kent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Patio
    • Cooker
    • Air Conditioning
    • Internet Access
    • Dryer
    • Refrigerator
    • Stereo System
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled in the heart of the village, this private get-away awaits you. Relax and still be in the center of everything. 2 bedrooms, 1 1/2 baths and charming backyard. There is wifi, fully equipped kitchen and a washer dryer. Off street parking. You can walk to 4 restaurants, 2 bakeries and many... View all property information
    Make Enquiry
    Location Information
    Kent, Connecticut 06757
    5 of 5 stars Reviewed 28 June 2015
    Beautiful and brand new tastefully renovated duplex in most picturesque house on Kent's Main Street. Fully equipped and convenient. Karren, the property's owner is generous and...
    See all reviews
    Get the List
    From
    €133
    / Night
    View Details
    1 / 22
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Satellite TV
    • Stereo System
    • Air Conditioning
    • Internet Access
    • Deck
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from West Cornwall and its covered bridge,10 minutes from... View all property information
    Make Enquiry
    Location Information
    West Cornwall, Connecticut 06796
    From
    €241
    / Night
    View Details
    1 / 28
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Deck
    • Internet Access
    • Stereo System
    • Private Outdoor...
    • Fireplace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SUMMER RENTAL LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful , very private country setting; four bedrooms, large family room with cathedral ceilings; grand piano. All amenities:cable TV, CD, DVD,VCR, internet. All rooms are with AC. Deck by the house with screen house and gas... View all property information
    Make Enquiry
    Location Information
    New Milford, Connecticut 06776