Dog Sitting in Winsted
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Top rated Winsted dog sitters

“Caroline is great! She is friendly, takes great care of our dog, doesn’t leave any mess, and is super responsive to messages! We will definitely continue to use her to take care of our pets 😊”



“We're so glad we were able to book Kristy and Chris to do drop-ins for our cat while we were on vacation over the weekend. Kristy and Chris were extremely professional and took detailed notes on the instructions to care for Pemi. We really appreciate their courtesy and timeliness. Would highly recommend them to anyone else in the area!”


“Kiera was available on relatively short notice for a drop in. She spent time with my pup and sent along plenty of pictures. Everything was put back exactly as it was left, she was great!”



“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”


About: Other than owning dogs my whole life, my pet care experience has expanded through working with Educating Canines Assisting with Disabilities (ECAD) and through personal connections to house sit and take care of a variety of animals! My experience at ECAD included basic to extensive training puppies to 2 year old dogs, potty training, bathing dogs, understanding the importance of mental stimulation in dogs, playtime, dog walking (and training on how to walk / heel), understanding behavior (signs of enjoyment / fear / stress / separation anxiety, feeling threatened) with how to accommodate them, and cuddles of course! I also take care of senior dogs who require extra care and love and understand the importance of one-on-one care. I also have experience taking care of high energy dogs, dogs with medications, high maintenance dogs, multiple dogs, and different animals as well. I have taken care of a mixture of dogs, cats, lizards, etc simultaneously! I am always called to house sit for friends and family, whether it be for a drop-in visit, a walk, an overnight stay (one night, a weekend, or a whole week). I even was asked to watch a french bulldog while someone was using the bathroom at an airport! I have been told that I ensure trust in the owners and always give them a sense of relief during my stay and that they never have to think twice about their pets being taken care of and their home. I provide numerous check-ins during each day of my stay, plenty of pictures, and I am adaptable to changes in care / schedules when need be! I will treat your pet as one of my own! I understand the stress of a busy schedule and making sure your pet(s) are cared for is extremely important. Pet care fits into my daily / weekly routine due to the personal experience of owing multiple dogs at once and through my professional experience at ECAD. I understand the significance of making sure your pet is happy and well taken care of! I hope to achieve that with you! I care for pets in a clients home just the same as I would for my own pets. I accommodate to the dogs schedule and keep my care as familiar as I can to my clients. I am willing to make sure I keep my client and their pet satisfied and feel at ease. I will update my client numerous times a day, send plenty of pictures, and incorporate any accommodations / needs as necessary. I am extremely flexible and want to keep my client and their pet comfortable. Please let me know any accommodations or needs you have!

About: I’ve had dogs my entire life from Rottweilers to mastiffs. I’ve been pet sitting for over 10 years, and am comfortable with all breeds, ages, and sizes. I have done basic training with my own puppies, and even adult dogs. I can offer a calm and confident presence, I have flexible availability, and am a great communicator. I greatly appreciate the opportunity to work with you! I currently work 3 days a week, with flexible in office days. My work is done from home most of the time and I am available most days. I can offer a calm and loving environment. I enjoy walking and playing with my dogs, and can give a clean and safe space for them. I follow directions, and am respectful should I enter someone else’s home. I can follow routine, but also am flexible where it is needed. I can happily take on each pets individual needs.

About: Throughout my years in high school I was a caretaker of 3 dogs and 2 cats after school everyday of the week. I grew to care and love these pets like they were my own. I had so much fun taking them outside for their daily walks and playing catch around the yard, it was the best job I have ever had because it was loads of fun! Unfortunately, I had to retire my pet sitting job when I went to college back in 2012. Now I work from home and would love to start pet sitting again. I live in a house with a big backyard so it is the perfect place to play catch with them and I live in a residential area that loops around perfect to go for a nice walk too! I am available to start immediately and I am available every day of the week. Looking forward to hearing from you! I work from home so I am able to be home to watch, take them out and play with them most of the day. I work from 3-9pm but have several breaks in between. My yard is partially fenced in but I take safety very seriously when it comes to my own dog, so I will be just as safe with yours as well!

About: I have taken care of multiple pets since I was 6 years old. I have had dogs and cats and truly enjoy spending time with animals and providing quality care. I am available during work hours this summer, so I would be able to provide care any time during the week and at varying hours on the weekends. I currently would be more comfortable coming to a clients home to play/ give proper needs to a clients pet. I will take pets on walks and going to dog parks!

“Courtney was great! She sent me pictures every visit, checked in and out when she dropped in, took care of my plants, and when she dropped off my key, my cats ran to greet her, obviously having enjoyed the play time with her. I will definitely book Courtney again.”


“Angela is a reliable and caring pet lover. She is super flexible and very knowledgeable when it comes to the well being of like dog. We appreciate all the tips she has given us for our puppy. We will be using Angela again soon”

“RaeLynn has been such a blessing. Tribe has major anxiety due to trauma he suffered as a puppy, As a result he requires a lot of patience and honestly he just needed someone to see the sweet and loving boy that he truly is. I was really nervous to try rover, but reading RaeLynns profile I felt confident that my baby would be in good hands given her experience and training. And I was absolutely right. We ran into a few bumps along the way but through each step Tribe was treated with patient understanding, love and kindness. I am so grateful and will 100% be contacting RaeLynn for our future sitter needs. Thank you so much”


About: Hello! My name is Kaleigh. I’m twenty one years old, and I absolutely adore every fur baby around. It doesn’t matter what animal it is, I love all. I have always been surrounded by guinea pigs, hamsters, chinchillas, birds even. I owned a lot of chickens growing up, only for eggs, and i’ve had so many pups to spend my time with. I have a chihuahua who is a certified service animal, as I am diagnosed with epilepsy. I am medicated for that and all seems well. My boyfriend lives with me and typically comes if I take care of pets, but I can make arrangements if needed, just isn’t preferred because it’s a lot easier for the ride factor. I love to write poetry, make music, I draw frequently, and I went to a technical school for culinary as well. Thank you for reading about me. I currently do not have a full time job. I have worked prior at a camp that helped disabled people and nourishes them in the ways they deserve. I’m a stay at home and I help my mom & dad with my dogs and cats, but i’m free any day of the week, as long as it’s known a day ahead, but I would also take emergencies. I have a fenced in yard, but it’s big enough to where my dogs are able to explore around the yard and look through, so they’re still living their best lives. My chihuahua loves to sit on our porch, it’s the first place she runs to in the morning to lay in the sun. She also loves going on rides and exploring the world, going on adventures.

“Katie took such good care of my kitties! She stopped in prior to our scheduled pet sitting to meet my cats, which was much appreciated. She did everything I asked, and made an effort to give my kitties some playtime, even though they were being shy. She provided lots of pics and feedback after each visit, which I love to see, as I worry about my girls when I can’t be home with them. We will definitely be using her services again! ?”


About: Animals have always been a big part of my life — I’ve grown up with both cats and dogs and currently have two dogs and three cats of my own. I started pet sitting and house sitting at just 13 for neighbors and family friends, and over time I built a small network through word of mouth. Over time I have taken care of many pets with many different needs and personalities. Whether it’s a cozy cuddle session or an energetic walk, I treat every pet like they’re my own. While I work full time during the week, I'm available after 4 PM Monday–Wednesday and after 5 PM on Fridays. My weekends are wide open so you can have worry-free coverage while you're away! When caring for pets I prioritize their safety, comfort, and well-being above all else. I follow any specific instructions you provide, from feeding schedules to medication administration, and keep a close eye on your pet’s behavior to ensure they feel happy and secure. I maintain a clean, pet-friendly environment and make sure they get plenty of love, exercise, and mental stimulation. Communication is key, so I keep you updated regularly with messages and photos to give you peace of mind while you’re away. Your pet’s trust and safety are my top priorities.

“Sara was amazing with all of my dogs. She came and met them and they were at ease with her as soon as they met her. she sent pictures and updates and kept us informed. She is our new go to doggie sitter!!!”


About: Hi everyone, I’m Amanda! Currently a stay at home mom raising my 5 and 6 year old human children, and my 7year old mix and crazy kitten! We’re all avid hikers and nature lovers, being outside is our absolute favorite! I grew up having dogs, mostly mixes and rescues, so I know how to gently approach pets that may have trust issues or who may be shy. With our mix having husky in her, I know all about high energy and how to get them relaxed and sleepy! Walking, running, and hiking are what we use to personally exercise our dogs so I can make sure whatever works best for your pup is what we’ll do! If needed I can be open to at home boarding, but I would first need to be sure they’d get along with my dogs :) Thank you for reading! I'm currently home full time with my kids in school, so I'm available from 9A - 2P (depending on distance) and after 5 during the week, as needed on the weekends. We have a large yard, and lead available for dogs who may need it. Currently our dog does well to stay on our property, she loves walking down to the brook for a dip!
Loving dog sitters in your neighborhood
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Caroline G.Star Sitter

“Caroline is great! She is friendly, takes great care of our dog, doesn’t leave any mess, and is super responsive to messages! We will definitely continue to use her to take care of our pets 😊”




Kristy & Chris B.


“We're so glad we were able to book Kristy and Chris to do drop-ins for our cat while we were on vacation over the weekend. Kristy and Chris were extremely professional and took detailed notes on the instructions to care for Pemi. We really appreciate their courtesy and timeliness. Would highly recommend them to anyone else in the area!”


Kiera K.

“Kiera was available on relatively short notice for a drop in. She spent time with my pup and sent along plenty of pictures. Everything was put back exactly as it was left, she was great!”




Lynsey M.

“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”


Julia B.Star Sitter
“Julia has watched the two of my cats on numerous occasions for overnight stays. She goes above and beyond every time! From feedings, to litter cleanings, and even giving one of my cats his inhaler, I can take comfort knowing they will be taken care of with the same level of care that I do myself. She is highly communicative and prompt in answering about any questions I have regarding the boys. I highly recommend Julia as a sitter!”


Elizabeth B.
About: I’ve had dogs my entire life from Rottweilers to mastiffs. I’ve been pet sitting for over 10 years, and am comfortable with all breeds, ages, and sizes. I have done basic training with my own puppies, and even adult dogs. I can offer a calm and confident presence, I have flexible availability, and am a great communicator. I greatly appreciate the opportunity to work with you! I currently work 3 days a week, with flexible in office days. My work is done from home most of the time and I am available most days. I can offer a calm and loving environment. I enjoy walking and playing with my dogs, and can give a clean and safe space for them. I follow directions, and am respectful should I enter someone else’s home. I can follow routine, but also am flexible where it is needed. I can happily take on each pets individual needs.


Rebecca P.
“Rebecca takes care of dogs like they are her own. She makes sure they have food and water and takes them out every hour. She also plays with them and then at night she curls up into bed with them (if they are allowed to that is.) you have nothing To worry about when rebecca watches your dogs because they are always in good hands.”


Julia P.
About: I have taken care of multiple pets since I was 6 years old. I have had dogs and cats and truly enjoy spending time with animals and providing quality care. I am available during work hours this summer, so I would be able to provide care any time during the week and at varying hours on the weekends. I currently would be more comfortable coming to a clients home to play/ give proper needs to a clients pet. I will take pets on walks and going to dog parks!


Courtney D.

“Courtney was great! She sent me pictures every visit, checked in and out when she dropped in, took care of my plants, and when she dropped off my key, my cats ran to greet her, obviously having enjoyed the play time with her. I will definitely book Courtney again.”


Angela W.
“Angela is a reliable and caring pet lover. She is super flexible and very knowledgeable when it comes to the well being of like dog. We appreciate all the tips she has given us for our puppy. We will be using Angela again soon”


Amanda O.

“Prompt, thoughtful, and communicative. Highly recommended!”


Raelynn M.


“RaeLynn has been such a blessing. Tribe has major anxiety due to trauma he suffered as a puppy, As a result he requires a lot of patience and honestly he just needed someone to see the sweet and loving boy that he truly is. I was really nervous to try rover, but reading RaeLynns profile I felt confident that my baby would be in good hands given her experience and training. And I was absolutely right. We ran into a few bumps along the way but through each step Tribe was treated with patient understanding, love and kindness. I am so grateful and will 100% be contacting RaeLynn for our future sitter needs. Thank you so much”


kaleigh f.
About: Hello! My name is Kaleigh. I’m twenty one years old, and I absolutely adore every fur baby around. It doesn’t matter what animal it is, I love all. I have always been surrounded by guinea pigs, hamsters, chinchillas, birds even. I owned a lot of chickens growing up, only for eggs, and i’ve had so many pups to spend my time with. I have a chihuahua who is a certified service animal, as I am diagnosed with epilepsy. I am medicated for that and all seems well. My boyfriend lives with me and typically comes if I take care of pets, but I can make arrangements if needed, just isn’t preferred because it’s a lot easier for the ride factor. I love to write poetry, make music, I draw frequently, and I went to a technical school for culinary as well. Thank you for reading about me. I currently do not have a full time job. I have worked prior at a camp that helped disabled people and nourishes them in the ways they deserve. I’m a stay at home and I help my mom & dad with my dogs and cats, but i’m free any day of the week, as long as it’s known a day ahead, but I would also take emergencies. I have a fenced in yard, but it’s big enough to where my dogs are able to explore around the yard and look through, so they’re still living their best lives. My chihuahua loves to sit on our porch, it’s the first place she runs to in the morning to lay in the sun. She also loves going on rides and exploring the world, going on adventures.


Katherine C.

“Katie took such good care of my kitties! She stopped in prior to our scheduled pet sitting to meet my cats, which was much appreciated. She did everything I asked, and made an effort to give my kitties some playtime, even though they were being shy. She provided lots of pics and feedback after each visit, which I love to see, as I worry about my girls when I can’t be home with them. We will definitely be using her services again! ?”


Alyson P.
“I can’t recommend alyson highly enough! She has been walking our dog, for several months now, and the difference in our pup’s happiness and energy is incredible. She is punctual, responsible, and genuinely care about the dogs she works with. What I appreciate most is the peace of mind I get knowing my dog is in good hands. Alyson provides updates after every walk, is attentive to any changes in behavior or health, and treats our dog like their own. If you’re looking for someone trustworthy, friendly, and passionate about animals, look no further!”


Sara N.

“Sara was amazing with all of my dogs. She came and met them and they were at ease with her as soon as they met her. she sent pictures and updates and kept us informed. She is our new go to doggie sitter!!!”


Jillian A.

“Jillian was great! She took excellent care of my 5 chickens morning and night. Super reliable and easy to communicate with. Highly recommend!”


Amanda B.
“Amanda has gone above and beyond with the care that she has given to my dog. Our puppy can't wait for Amanda to arrive and will whine and cry until she reaches the door! She enjoys the long walks she goes on with Amanda and comes back tired and content. I highly recommend Amanda's services.”




Catherine R.

“Catherine is a perfect dogsitter. Trustworthy, my dog loves her, she is responsive, mature, intelligent, timely, she sends pics - 100% awesome! Wholeheartedly recommend her.”


Trinity K.

“Trinity does an excellent job with my girls. They love her visits and she is always on time and makes sure I get to see pictures of them while she’s there!”
Winsted dog parents share their Rover experiences
Trinity has helped watch our dog as we went away for several overnight trips this summer. Charlie loves Trinity and we know she's in great hands and getting lots of love and attention. Trinity is helpful, professional, and easy to communicate with,its been a positive experience every time and we highly recommend her to watch your pets!

Popular requests near you
Select a filter and find qualifying Winsted sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
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Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn't happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winsted.
Rover makes it easy to find Winsted dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
