Dog Walking Winsted
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

Over 5 pet parents in Winsted have booked dog walking
Winsted, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve been pet sitting for over three years. I’ve had various experiences with dogs and cats. As someone who has a dog of their own, I’ve been able to observe behaviors that’s helped when taking care of other dogs, to understand their needs and wants. I currently work remotely however, it doesn’t take time away when it comes to the fur babies! In fact, it allows me to be present and give them the much needed attention. I understand the environment the pets are settled in. I give daily updates to the home owner, making sure that any anxiety of leaving their pets behind is relieved. I bring my own food and care.
“Stacey is so incredible!!! She is communicative, flexible, and so kind. She took amazing care of my girl and went above and beyond to be helpful. A bear knocked over our recycling bin and she picked it all up, she brought a package in, and most importantly she made our dog so so happy!! We will call Stacey any time we need a little help with Blue going forward!”

“We met Katie for a meet and greet and scheduled a dog walk together. I have 2 rescues who are both anxious and get nervous with new people. She has been very patient with them and asked lots of questions to better understand their behaviors. Katie has been great with our dogs and they are warming up to her. I will definitely be booking with Katie again.”

About: I absolutely love dogs all shapes and sizes, when you book with me your dog will be in a safe and loving environment with me. it’s important to me that any dog i’m with at the time will have a fun and enriching environment with me and the time we’re spending together. I have experience training puppies and pet sitting puppies. I’ve done extended petting sitting stays and have done petting sitting with multiple animals, i’ve done week long stays with 6+ animals, so I can handle a big crew if you have it. I have experience with farm animals and horses as well if that’s ever needed as well! I’m currently working part time at a doggie daycare and boarding facility, I absolutely love working with the dogs and am just looking to do some more in my free time. I look forward to hearing from you :) If you use me for pet sitting you can expect your dog to be fully safe! I will follow your directions and expectations to the tea because I know what it’s like to have to leave your dog with someone and not wanting to have to worry about your loved one

About: I have over 15 years of personal experience caring for dogs of various breeds and sizes, including a Yorkshire Terrier, a Corgi, a Spaniel, and a Cane Corso. Living with both small companion dogs and strong large breeds has given me a deep understanding of different temperaments, energy levels, and care needs. I am comfortable handling everything from delicate toy breeds to powerful guardian dogs. I understand structure, consistency, and the importance of calm, confident energy — especially with larger breeds. I provide safe, attentive care including walking, feeding, playtime, and following detailed instructions. I treat every dog with patience, respect, and genuine affection, as if they were my own. Pet care fits well into my daily routine. I am available early in the morning through 2:00 PM on weekdays. On Saturdays and Sundays, I am available after 3:00 PM for afternoon and evening visits. I plan my schedule carefully to ensure each pet receives attentive, unrushed care and consistency. Your dog’s safety and comfort are my top priorities. I provide a calm, structured, and clean environment. I carefully follow feeding schedules, exercise routines, and any special instructions you provide. I understand the importance of supervision, especially with larger or more energetic breeds. I am attentive to behavior, body language, and stress signals to ensure every dog feels secure and respected. I treat every pet in my care as if they were my own.
“Theresa is the best! She provides highly individualized care and is so kind and easy to work with/ communicate with. She is very observant and competent with dog behavior and is the perfect match for our sweet energetic 11 year old boxer mix!”

About: I’ve been dog sitting for people my whole life. From shitzu’s, to lab mixes. I also have two rescues of my own who I’ve worked very hard with to make comfortable and feel loved after there trauma. I am currently a full time teacher so I’m available mostly weekends. Come summer time, other than a part time job I’ll be available often. I have two high energy dogs who love to play. We do not have a fenced in yard, but it is large with woods all around. We also have a lead set up for dogs who are a flight risk.

About: I have hands-on experience caring for and walking dogs, including my own Golden Retrievers, who I personally trained and walk regularly. I also care for two other dogs, so I’m very comfortable with different personalities and needs. I’m patient, reliable, and understand how important it is to keep your dog safe, happy, and well-exercised. You can trust that I will treat your pet with the same love and care as my own I’m currently working on part time and go to school, but I have morning availability, so I can make sure your dogs are taken care of early, giving you one less thing to worry about. I provide a safe, loving, and clean environment for all pets in my care. I make sure they are well fed, exercised, and supervised at all times. I follow your pet’s routine closely and ensure they feel comfortable and stress free. I also provide updates and will contact you immediately if there are any concerns or emergencies. Your pet’s safety and happiness are my top priorities.

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 grew up with dogs and have always loved caring for them. I currently have a mix breed, Marley who is my little sunshine. I enjoy hiking, running and watching cartoons with him haha. I know what its like finding someone who is trustworthy to care for my dog when I need to travel for work or personal vacation. It can be a bit stressful looking for a good sitter but I can assure you that your dog will be in good hands.
“Tara is wonderful. I recently needed someone to help walk my anxious and excitable rescue dog ( a 6-year-old Labrador-Golden Retriever mix). She bonded with my pet right away and was masterful and patient in keeping her calm and controlled. It was my first time using Rover and my first time leaving my dog with a stranger. Tara made me feel comfortable leaving my dog and she sent me multiple photos and updates of her visit. I look forward to working with her in the future.”

“My dog was calm and well cared for after his walk with Angela. She followed all my instructions and took lots of pictures of my my dog while she was with him. He looked like he was having fun.”

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.
About: Ive had pets my whole life, from reptiles to birds to our furry friends. Ive done it all! Loving and caring for animals is one of my greatest passions, Ive been taught from a very young age to treat our lovely companions with the greatest kindness and respect. As a college student ill be able to take care of your pets before and after my classes! I of course can discuss details when booking! I am very detail oriented when it comes to our companions, I will adjust to the schedule you have set for them! As a pet owner i understand the importance of keeping your pets comfortable and happy.

About: I have helped raise 3 dogs growing up. As well as dog sitting my brothers german shepherd for a few years. I am young and social and I have plenty of friends with dogs so I am constantly playing, walking, feeding dogs. Current college student who is off for the summer with no other job besides coaching a local baseball team 1-2 days a week. I’m looking for a buddy to go outside with for fitness/wellness! I live a young and social lifestyle so I enjoy going outside for walks, whether it be around your neighborhood, or driving to a destination. I have no problem staying at your house for a requested period of time to watch after your pet and take care of anything they might need. I’m more than happy to come to my clients home if their Pet has the following… - House trained/ Potty trained - Proper Food - Medication (if needed)
About: I’ve taken care of multiple dogs since I was 14. I was a free-lance dog walker for my neighborhood so I’ve had plenty of experience with many kinds of dogs! I go to school part-time so I’ll be able to take care of your pups as long as I’m not in school. I enjoy taking dogs on walks as I enjoy being active. I have plenty of toys to keep your pups busy as well as my own dog, Tucker, to keep them company! I will play with them and give them as much attention and love as I can.
About: What sets me apart is my hands-on experience and genuine love for dogs of all ages. I worked at a dog kennel for two years, where I cared for dogs with all kinds of temperaments, ages, and needs. I’m experienced with senior dog care and I’m comfortable with puppies too—whether it’s crate training, potty breaks, or just keeping up with their energy! Your pet’s comfort and safety are always my top priority. Pet care fits easily into my weekly routine since I have a pretty open and flexible schedule. I’m most available Tuesday through Friday between 11:30 AM and 4:30 PM, which works great for midday walks or drop ins. That said, I’m always happy to discuss and make arrangements that work best for you and your pet! Whether I’m caring for pets in my home or yours, their safety and comfort always come first. I take the time to understand each pet’s routine, needs, and personality to make sure they feel secure and loved. I keep a clean, pet-friendly environment and follow any instructions you provide whether that’s feeding schedules or favorite toys. I also provide regular updates so you can feel confident and at ease while you're away.
About: I have had dogs my whole life but 2 of my dogs gave birth to 11 puppies in October of 2022 and I helped take care of them all until they were ready to go to their new homes. I kept one of the puppies and have taken care of her since she was a newborn so I am very familiar around all types of dogs. I’m currently available most weekdays and weekends. I keep my calendar up to date and do my best to accommodate last-minute requests whenever possible. Feel free to reach out with your dates, and I’ll respond as quickly as I can. I will make sure your pets are getting enough attention and exercise when you are away and will treat them like they are my own.
“Karina is the best dog sitter that I’ve had. She is very professional and always communicates. I have been though a few dog sitters so far, and she is definitely the best. Don’t be afraid to give her a booking you won’t regret it!”
About: I have taken care of pets since I was a little girl. I have had two long term jobs at different dog kennels. Which then resulted in me being able to acquire multiple pet sitting jobs. I have experience in pet sitting, dog walking, dog daycare, and some dog training! I am currently a stay at home mom. Both of my children will be starting school soon and I would love to get back into doing what I love with pets! I will make sure to spend as much time with your pet as you desire. Making sure they get all the love,food,treats and playtime they need to make everyone happy!
The median cost per walk for dog walking in Winsted is $22
Dog parents share their Rover experiences - Winsted
Stacey is so incredible!!! She is communicative, flexible, and so kind. She took amazing care of my girl and went above and beyond to be helpful. A bear knocked over our recycling bin and she picked it all up, she brought a package in, and most importantly she made our dog so so happy!! We will call Stacey any time we need a little help with Blue going forward!

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.
Meet local walkers who will treat your dogs like family

1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
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 for dog walking - Winsted
Select a filter and find qualifying sitters offering dog walking.Sitters in Winsted average 3 repeat dog walking clients
FAQs for Dog Walking - Winsted
Frequently asked questions about Rover
The average cost for Dog Walking in Winsted on Rover is $27.75 per walk (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .
As of August 2026, there are 1,751 sitters on Rover offering Dog Walking across Winsted. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winsted. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winsted.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.
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.
Every walker 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winsted. On Rover:
- 97% of walkers can help with special care needs
- 95% can help with giving oral medications or injections
- 100% 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.
A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.
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 walker.
