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.
“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.”
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 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!
About: I grew up with dogs all around me. My household, my families' households, I was never around any less than three pets at a time! I've taken care of dogs, cats, horses, birds, lizards, fish, rats, and pretty much any other pet you can think of over the years. I like to humbly boast my knowledge of care and training working with disability dogs. From wheelchair assistance to emotional support, I’ve worked with all manner of dogs from all ages! I work part-time at Lime Rock Park, and will be available during most weekdays because of this! Outside of major events I can also sit during weekends given prior notice. Unfortunately I am not currently available to sit at my own home, however I am more than happy to provide extended time for nightly stays given this! Please feel free to ask. Safety is always my #1 priority. Fun and enrichment is my #1.5! Your pet will be well treated to plenty of play time, restful naps, and as many treats as you will allow them to have!
“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: I’ve taken care of dogs on and off for years and I’ve had a couple of my own. Would be happy to host your pet for a day or a few days, whatever your need is. I am fully retired at this time and will have plenty of time to play with and care for your pet. I am available weekdays and nights as well as some weekends. I am also available to watch them at your house as well if you’d prefer. I am happy to follow your feeding schedule and to take your pet for a daily walk. There are no young children or anyone else living in the house except me.
“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.”
“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.”
“Caroline was amazing! I had a last minute request for a drop in visit for my dog and she was super quick to respond, very communicative and was wonderful to work with. I would definitely rebook her the next time I need someone to walk my dog! Thank you, Caroline!”
About: My entire life I’ve taken care of dogs from tiny Shih Tzu’s to large and in charge Cane Corso’s and everything in between! (I’ve helped with litters too!) I’ve also taken care of Bearded Dragons, Ferrets, Rats, Fish, Persian cats, etc. so I’m most definitely comfortable with the large variety of animals! I’m also a certified dog groomer! Therefore I have tons of experience reading dogs’ body language to ensure a comfortable and safe environment for the both of us. Please do not hesitate to message me if you have any questions. I have a few professional references if needed :) I’m currently a stay at home mom therefore, I have plenty of time to play with your furry friend! I’m super flexible please message me with any questions! Anytime my dogs need to go outside to use the bathroom they’re always supervised! I live on a pretty quiet road therefore traffic shouldn’t be a concern with your pups safety. I also have a large yard therefore there’s plenty of room to run around & get some energy out!
“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: 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.
“Melanie has cat sat for us multiple times & she is the best! She is trustworthy, responsive, and keeps us informed daily with Rover report cards!! We will hire her again! Lots of paws and thumbs up! 5 stars all the way!”
About: Hi there! I’m Kaylee, a passionate and experienced pet care professional. With 5 years of hands-on experience in animal care, I have worked across a variety of environments, including doggy daycares, boarding facilities, and grooming salons. My background has given me a deep understanding of animal behavior and the specialized care different pets require. I truly love what I do—caring for your pets brings me so much joy, and I am committed to providing them with the same love, patience, and attention they receive from their family! I am very flexible and happy to work around your schedule. To make sure I am the perfect match for you and your pet, I offer a complimentary meet-and-greet before our first booking. This gives us a chance to get to know each other and ensures your pet feels comfortable and excited to see me! Have any questions? Please feel free to reach out. I would love to chat about your pet care needs and how I can help! My Approach to Care I understand that every pet is unique, with their own personality, routine, and set of needs. I pride myself on providing personalized, attentive care tailored specifically to your pet's requirements. Whether your dog needs extra exercise, a specific routine, or just some extra companionship, I am here to help.
“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”
The median cost per visit for dog sitting in Winsted is $22
Book with peace of mind
- 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?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winsted sitters!Sitters in Winsted average 5 repeat dog sitting clients
FAQs for Drop-In Visits - Winsted
Frequently asked questions about Rover
The average cost for Dog Sitting in Winsted on Rover is $27.75 per visit (as of July 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 July 2026, there are 1,787 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.
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