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

Over 16 pet parents in Winsted have booked dog sitting
Winsted, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Ashley took amazing care of our two kitties while we were on our honeymoon. We were able to have a stress-free trip knowing we could count on her to be there twice a day to feed them AND spend time with them! I will definitely be booking Ashley next time we go away, and you should too! She’s very sweet and intentional with animals. ❤️”

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.
“Amanda was great! She was consistent and made sure my cats had everything they needed. Including taking care of cleaning the cat bowls and picking up after one of them got sick. She gave good updates. Would use again and recommend to others.”

“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! ?”

“First time having him walk oaks....he's amazing definitely rebooting he's kind patient deals w my foxhound bordercollies quirks .....best walks ever for ms oaks ....she loves his visit...can't wait to rebook”


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: I’ve had and taken care of cats my whole life. Friends and community members have relied on me for all of their pet care needs. I currently work a part time job with non-consistent hours. My best availability is on the weekends but I can make any weekday hours work. I do not offer any doggy daycare or boarding services, however I can effectively offer all pet care services from staying at your house to keep your pets happy to stoping by and walking, feeding, and having play time with your pet.
About: I grew up with as many as 5 cats and two dogs at a time. I am familiar with caring for most pets including rodents and fish. I work from home so taking a break to walk or feed pets is not an issue. There is even some extra time to give them some attention too! My dog has free roaming permission in the backyard and we also have a cage for large dogs available. For visiting dogs we walk them on a leash since they are not familiar with the area.
“She did a wonderful job eith my cats. They did hide on her but if I had her a few more days I am sure they would have liked her. If there is ever a time when I need a cat sitter again, I will hire her again”

About: Thank you stopping to read my profile! My name is Ellen. I am a lifelong dog owner. Presently I have one dog Harry, who is a 10 year old Wheaten Terrier. I have three grown children, and have lived in my home for 35 years. Watching dogs has brought me a lot of happiness and I look forward to potentially meeting your pup. Above all, I value safety. I provide a safe, loving, and engaging environment for dogs of all ages. I have a large yard that backs up to a park and the walking trails, so your pup has plently of room to explore and play - perfect for dogs who enjoy regular walks and outdoor adventures! As a life long dog owner and dog lover I have experience caring for them at every stage of life—from energetic puppies to gentle seniors—and I tailor each visit to your dog’s needs, whether they prefer active play or a more relaxed stay. I do have dog beds and bowls, but if your dog has a special bed, bowl, toy, that would make them feel more at home than please don’t hesitate to bring them along. Your dogs safety and happiness matters!! Every dog is unique, and I want to make sure yours feels safe and happy during their stay. Please let me know if your dog has any specific needs - such as dietary restrictions, separation anxiety, treat limitations, or known triggers- so I can provide the best care tailored to them. I offer: One-time drop-ins, recurring daycare and overnight stays. Whether your dog loves long walks or prefers quiet days, I’m here to make their time away from home as comfortable and joyful as possible. Pet care fits into my scheduyle as a non-negotiable daily routine that starts early to ensure your pet is fed, excercised and settled before I begin my day. I block 20-30 minutes each morning for a quick walk and play time. I have a trusted caregiver in the event of an emergency. Meet and greet introductions, emergency contacts, including veteranian and backup caregiver. My home is safe and secure from and toxic foods, I will provide gates if necessary, learn leash and harness preferences, feeding and medication schedules, routines, any protocols I need to be aware of for safety. Safe and happy place for your pup!
“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.”

About: I've been taking care of my own pets for 6+ years. I make sure pets feel loved and well-cared for, whether it's playtime, feeding, or just giving them some extra snuggles. I understand that each pet has unique needs and preferences, so I adapt my approach to suit their individual personalities. Devoted and loving pet caretaker available around the clock. With a very flexible schedule, I can provide frequent walks, playtime, and feeding to keep your pets happy and healthy. I have a yard for your pet to play in with supervision. I have a small dog and cat that are friendly, But they can be moved to another part of the house if you prefer.
About: Welcome, y'all! I love watching dogs. We watch kitty cats too 😁. Cheapest rates around! Let me make it easier for you to celebrate your vacation and holidays! Let me sit for your pup. I...love... dogs! My parents were dog breeders for years. As a youngster, I was responsible for many of the chores. As an adult, I have always had pets. I know how important your dog is to you. Your dog is your 'baby'. We are definitely dog lovers in this house! Big dog specialist. I love the little dogs too, though! ☺️💪🎄🎁❤️🩹 I will treat your pup like my own. I am a teacher during the day. I'm usually home by 3. I'm home every afternoon and every night and every weekend. I do have flexibility in my work schedule should they need arise. I have a dog lead hooked up to the house and it goes all the way back to the maple tree on the back of the property. 20 ft in either direction gives Fido plenty of room to go to the bathroom. Otherwise, your pup is in the house with me and my family. I am offering dog boarding services. This is a friendly Christian home. Lots of love to share.
About: I’ve taken care of small-medium dogs short-term and long-term. Friends and family know my love for dogs and always call me for dog sitting. I want to get one of my own soon! I’m currently working from home and have lots of flexibility. I also love to go on short and long walks myself and would love to help someone out and walk a pet while I go for my walks! After pet sitting in the past, I’ve been told I did a wonderful job and that their pet loved being with me. I offer a fun and caring environment, follow schedule as provided, and go out for many walks. I’ve usually done sitting at the clients home so the pet is most comfortable in its own home.
About: I have over 5 years of experience caring for dogs, cats, and other pets. I provide dog walking, drop-in visits, overnight care, pet transportation, feeding, playtime, and medication administration when needed. I understand that every pet has their own personality and routine, and I always strive to make them feel safe, comfortable, and loved while their family is away. I truly enjoy meeting new pets and caring for them as if they were my own.🐾❤️ Pet care is already a part of my daily routine, and I do my best to accommodate each pet's individual needs. I offer dog walking, drop-in visits, overnight stays, pet taxi services, and care for both dogs and cats. Since my availability can vary, please feel free to send me a message with your requested dates, times, and care needs. I respond promptly and will let you know as quickly as possible if I am available and how I can help. I I provide a safe, calm, and loving environment for every pet in my care. I carefully follow each owner's instructions regarding feeding, medications, exercise, and routines. I pay close attention to behavior changes and make sure pets always have fresh water, a clean space, and plenty of affection. Whether in my home or yours, I treat every pet as if they were my own.
About: I have worked with animals for a while. This includes all breeds and all ages. I am working on getting my vet degree and currently work in a vet office. I am able to medicate, walk and help with basic training. I am currently working part time. My schedule does change week by week, but I do always get it in advance. I am available to do walks in the afternoon and night. I can also do sit in services if you would like. I live in an apartment with a couple dog parks around. We go on daily walks and when we can we play ball in the parks.
About: Taken care of different breeds, small and big dogs, cats and small critters. Trained dogs used for disabilities. I walk small dogs with a harness only, and don’t allow them to jump from high places, due to their tiny bones. I make sure they are secured before opening any door where they might run off. I have an Instagram page where I upload dogs I meet , dogs I take care of or watch , dogs that were placed in safe homes. I will take photos to give updates. Can change day to day but if notified ahead of time , can usually work around my schedule. I do check my texts and email if something changes. My dogs are sociable, always keeping an eye out, they are like little kids. There is currently a Japanese Chin, Shitzu, Pekingese, Saint Bernard, a cat, a bird and 3 guinea pigs, in the home.
The median cost per visit for dog sitting in Winsted is $24
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- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Winsted
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winsted average 5 repeat dog sitting clients
FAQs for Dog Sitting - Winsted
Frequently asked questions about Rover
The average cost for Dog Sitting in Winsted on Rover is $27.75 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of September 2026, there are 1,754 sitters on Rover offering Dog Sitting across Winsted. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winsted stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winsted choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winsted with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winsted. On Rover:
- 97% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 99% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.



