Dog Sitting in Winsted
Book a Winsted dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Winsted dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

About: Animals have always been a big part of my life. I have experience working at a dog daycare and providing pet-sitting services for friends, family, and clients. I am comfortable caring for dogs of all sizes and personalities, including feeding, walking, playtime, and following specific care instructions. I am dependable, attentive, and committed to making sure every dog feels safe, comfortable, and loved while their owner is away. My goal is to provide peace of mind and quality care for both pets and their families. 🐾 Pet care fits naturally into my daily routine because caring for animals is something I genuinely enjoy. I have a flexible schedule and make it a priority to provide reliable, consistent care. Whether your pet needs walks, feeding, playtime, drop-in visits, or overnight care, I will make sure they receive the attention, exercise, and companionship they need Your pet’s safety and comfort are my top priorities. I carefully follow all care instructions, including feeding schedules, medications, exercise routines, and any special needs. I take the time to build trust with each pet and ensure they feel comfortable while you’re away. I will treat your home with respect and provide regular updates so you can have peace of mind knowing your pet is in caring and responsible hands. 🐾
“My husband and I knew upon meeting Tara for the first time that she was the perfect fit with our cat, Charlie. Charlie is very shy and usually hides when people come to visit. However, this was not the case when Tara entered our home. Tara did a top-notch job taking care of Charlie during her drop in visits over a period of one month. We were so happy when she sent up pictures and updates. Tara is reliable, kind, professional, and a true animal lover. Cats can be messy with the litter, etc. But with Tara on the job, we came home to a very neat home and well-fed, content cat. We will definitely seek Tara services again. Furthermore, we highly recommend her. Thanks a million, Tara.”

“April was terrific to work with. She sent me a daily update and pictures and I knew my kitties were safe with her. Excellent communication also. I highly recommend April to care for your pets.”

“Beyond my expectations. My dog is gaurded with strangers and is a big boy, but zach has a natural comfort with dogs you can tell. My dog wylie warmed up to Zach with ease. Will definitely seek out Zach again”
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!
“Caroline watched our dog pack for a week doing multiple drop-in visits a day. She was responsible, took great care of our dogs, cleaned up after them and kept us updated with pictures & notes after every visit. We highly recommend Caroline to take care of your doggy loved ones! Thanks again!”

“Meaghan was incredible babysitting our, at times, difficult and needy cat Ashley. Despite a few growls and a hiss at first, Meaghan kept earning our cat’s trust with each visit which is a huge success when it comes to our kitty. Having Meaghan watch our cat while we were away helped our stress levels immensely and I will certainly be hiring her for our next trip.”


About: When I was 10 I joined a dog training program through my school, that’s where my training experience began. I provide a premium, low-volume dog care experience for owners who want their dog to have more one-on-one attention in a calm home environment. Your dog won’t be just one of many in a crowded space. I keep my care more personal so each dog gets plenty of attention, supervision, and outdoor time. I have a big yard for dogs to enjoy, but my indoor space is smaller, so I am very intentional about keeping the number of dogs low. That means I can focus on your dog’s comfort, safety, and overall experience much more closely. This is a great fit for dogs who do better with a quieter setting and for owners who value quality of care over high-volume boarding or daycare. I generally only take one to a few dogs at a time unless they are from the same household. I have a lot of experience with senior dogs. I took care of my childhood dog for 17 years of her long, beautiful life. I have experience working with small senior dogs specifically and I know all the little things that they appreciate. I also have experience with large dogs and can handle very big strong dogs. I also love hiking with dogs so if you have an energetic dog you need to burn off energy I am your guy. I have an acre yard with a fenced in front yard in a nice area. Any dog that boards with me would be treated like my own dog and let out very frequently to go to the bathroom and play outside. I would always remain home with your dog. Thank you for considering me and I hope to meet your pet soon! I’m currently a fully remote student so I am fully available. If I board a pet I will be with them full time to make sure they receive the care they deserve. I have a fenced in front yard, and a good amount of unfenced land in the back. My dog is very friendly and would keep your pet great company. He loves dogs and cats. I can easily crate your dog if needed, but would love to give your dog the pet experience and treat them like my own. I live in a nice are and have great access to the woods nearby as well.
About: Hey, I’m Anissa! I have always been a huge animal lover! I currently have a cat but I adore all animals and will treat your pet like they are my very own. I have fostered many animals and have also volunteered at animal shelters so I know that I am qualified to care for your fur baby. I am very loving and playful with all animals and whatever the task, I will do it with the biggest smile on my face. Also, I speak English and Spanish, just in case you speak one better. I currently work full-time but am free to do drop-ins and boarding on the weekends, as well as drop-ins on weekdays after 6 p.m. Working on making this my full-time gig! I will stick to their routine, keep their space clean, offer TLC, monitor their health, and keep you informed. As well as lots of pets and treats (if allowed) for your pet!
About: I do have veterinary experience. Have taken care of friends dogs for many years. Basic experience with grooming and nail trims. Also have cat care experience. I currently work early AM shift at my regular job. I am available after 11am for walks and check ins.I am unavailable on weekends at this time I have experience with giving medicine,oral and injectable. Feeding,and medication instructions will be followed to a T. If special accommodation is need,please let me know,so I can plan accordingly.
About: I have experience caring for a variety of pets including dogs, cats, and birds. While it has been quite a few years, I was a veterinary technician in high school and college. I love all animals and feel comfortable around dogs of all sizes. I am a second grade teacher looking to share my love of animals while earning extra income during the summer. I am a second-grade teacher with two high school children. I can be available most days during the summer due to my career. I am also available most afternoons/evenings during the school year. I will ensure any specific instructions are followed with care and accuracy and make your pet feel comfortable and loved. I can support the needs of both active and relaxed dogs, and love to provide a cozy lap and/or be a throwing companion for your furry family member.
About: I have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.
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!
“Great visits with Sky - gave him lots of love and attention and always made sure to keep us updated with pictures. Ensured he was fell fed and watered and always had a clean litter box....”

About: I’ve worked at animal hospitals for 28 yrs I’m reliable and good with peoples pets I can give meds if needed insulin as well I get lots of waging tails my way I prefer come to your home so your pet is more comfortable and has there familiar surroundings and all the things they’re used to toys their bowls, etc. I can stay the night if needed I like staying with pets at there home this helps also with stomach upsets and stress of being somewhere new and unfamiliar I like the pets to be able to keep there routine
About: I’m a really active individual and love being outside as much as possible! I have dog sat for various families with varying ages of dogs. I have no pets, so my full attention is for your pet! I’m a grad student at UConn for physical therapy. I live at home, and my class schedule is very light this semester. I will be around most hours of the day to care for your pet. I have a decent sized yard for your pets to get running time. I go on walks on bike paths and hiking trails often, and I would love some company!

About: I enjoy the outdoors and taking a walk. Your dog will have lots of play time, as well as fun, treats, food and water. I just like having a dog around to keep each other company so they are not home alone for long time period, you know getting into mischief we can do that together and have more fun haha. I currently do not have any dogs but will get one when the time is right. I have enjoyed and attended dog shows showing for obedience and agility(Dalmatians). I also attended and passed the canine good citizenship test with my first dog. My second dog was adopted and we did agility and was a lot of fun. A dog is a companion in which you meet other dog friendly people. I'm currently working full time but would have time to care for your fur kid/s before and after work, get mail, water plants, check house. I do not have a fenced yard so would take your fur kids out on a leash at your home or if fenced and you chose for them to be loose at your home.
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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.



