Dog Walking Winchester

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Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ismael J.
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Ismael J.
from
$22
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
4 years of experience
Winsted, CT, 06098

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.

Sitter Profile Image: Stacey G.
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Stacey G.
from
$35
per walk
5.0 out of 5 stars
33 reviews
7 repeat clients
15 years of experience
Winsted, CT, 06098

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!

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Rachel C.
Sitter Profile Image: Katie O.
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Katie O.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
22 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

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.

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Molly R.
Sitter Profile Image: Olena G.
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Olena G.
from
$20
per walk
15 years of experience
Winchester, CT, 06098

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.

Sitter Profile Image: Theresa C.
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Theresa C.
Star Sitter
from
$45
per walk
5.0 out of 5 stars
81 reviews
29 repeat clients
52 years of experience
Torrington, CT, 06790

Great personality!!!…Theresa is professional, accommodating and a lover of animals which is so apparent when she’s with them. So glad we found her!

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Jacqueline H.
Sitter Profile Image: Alina M.
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Alina M.
from
$20
per walk
1 year of experience
Winsted, CT, 06098

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.

Sitter Profile Image: Kevin D.
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Kevin D.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Harwinton, CT, 06791

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.

Sitter Profile Image: Tricia C.
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Tricia C.
from
$30
per walk
11 years of experience
Torrington, CT, 06790

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.

Sitter Profile Image: Ashley A.
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Ashley A.
from
$18
per walk
4.9 out of 5 stars
40 reviews
9 repeat clients
10 years of experience
Salisbury, CT, 06039

Ashley is a delight. She was very communicative and caring about our elderly dog with special needs. We only needed her to come and take him for a walk, but he is blind and deaf and also wears a diaper. She let us know when she got to our house and sent pictures afterwards. We felt very comfortable with her and will definitely be using her again.

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Terri L.
Sitter Profile Image: Angela W.
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Angela W.
from
$35
per walk
5.0 out of 5 stars
117 reviews
45 repeat clients
15 years of experience
Torrington, CT, 06790

Angela has been a gift to us and our new fur baby! She gives us tips on training, great updates on how the walk goes and is always available when needed. She also clipped our dogs nails! 10/10 would recommend!

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Rebecca T.
Sitter Profile Image: Connor D.
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Connor D.
from
$15
per walk
5.0 out of 5 stars
1 review
1 repeat client
2 years of experience
Unionville, CT, 06085

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)

Sitter Profile Image: Aaliyah R.
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Aaliyah R.
from
$20
per walk
22 years of experience
Northfield, CT, 06778

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.

Sitter Profile Image: Kelsey L.
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Kelsey L.
from
$25
per walk
5.0 out of 5 stars
26 reviews
9 repeat clients
17 years of experience
Farmington, CT, 06032

Kelsey was great with Gigi- she was prompt and sent pictures and videos. I will definitely use Kelsey again. I know Gigi is in good hands with her.

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Karen C.
Sitter Profile Image: Jeffrey S.
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Jeffrey S.
from
$55
per walk
30 years of experience
Falls Village, CT, 06031

About: Hi I'm Jeff an experienced and professional pet sitter, dog walker, and provider of overnight pet care, I offer loving, dependable service that brings complete peace of mind. Whether it's daily visits or extended stays, your pets are treated like family every step of the way. I'm fully licensed, insured, and bonded, and certified in Dog and Cat First Aid & CPR—so you can rest easy knowing your furry companions are in safe, experienced, and genuinely caring hands. I have over 25 years of construction experience. I also offer Handyman Services which can be done while I am at your home. 🐾 Licensed, Insured, and Bonded • Certified in Dog & Cat First Aid and CPR Caring for animals isn't just something I do—it's my full-time profession, my livelihood, and my passion. I take great pride in providing dependable, compassionate care for pets of all kinds, including dogs, cats, birds, fish, chickens, goats, rabbits, hamsters, gerbils, and more. When you entrust me with the care of your beloved companions, I go far beyond basic walks and feeding routines. Their happiness, comfort, safety, and well-being are always my highest priorities. While I know I can never replace your presence, I work hard to provide the love, attention, companionship, and personalized care your pets deserve while you're away. To make life easier for my clients, I also offer handyman and home care services. Whether it's watering plants, bringing in mail, managing trash and recycling, hanging pictures, completing small repairs, painting, or helping with other household tasks, I'm happy to assist while caring for your pets and home. By combining professional pet care with reliable home services, my goal is to give you complete peace of mind, knowing your pets are loved, your home is cared for, and everything is being looked after by someone who genuinely cares. 🐾❤️🏡 When you entrust me with the care of your furry companions, I go above and beyond basic dog walking and playtime; I prioritize their happiness and welfare. Understanding that I can never replace your presence, I tirelessly strive to complement your affection and care by providing the attention and love your pets deserve, even in your absence. I also integrated handyman services into my offerings, recognizing the convenience and practicality of addressing tasks while caring for your pets. Whether it's watering your plants, hanging a picture, managing waste or recycling, or even handling small repairs and painting, I am here to help. Through this fusion of pet care and handyman services, my aim is to simplify your life while ensuring the well-being of your cherished pets and your home.

Sitter Profile Image: charleen m.
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charleen m.
from
$18
per walk
2 years of experience
torrington, CT, 06790

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.

Sitter Profile Image: Zachary N.
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Zachary N.
from
$20
per walk
3 years of experience
Torrington, CT, 06790

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.

Sitter Profile Image: Karina & Jared S.
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Karina & Jared S.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
138 reviews
62 repeat clients
23 years of experience
Barkhamsted, CT, 06063

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!

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Benjamin T.
Sitter Profile Image: Melanie D.
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Melanie D.
from
$25
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
14 years of experience
Southwick, MA, 01077

About: I have had a passion for animals since I was little! I love meeting new furry faces and making friends! Snuggles and belly rubs are a must! I bring treats with me to work for all the pups I see on my route! If it’s nice out, I enjoy running around outside or going on hikes. If it gets cooler, I prefer stretching out on the couch. Car rides are always welcome! Visits to the dog park are fun too! Even if they’re safe off leash, I’ll always keep them on leash to prevent any accidents! Muzzled or non-muzzled, I’ll be happy! If you have a list of what they need for food or other supplies, I should be able to follow it no problem!

Sitter Profile Image: Aislyn H.
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Aislyn H.
from
$20
per walk
5.0 out of 5 stars
3 reviews
6 years of experience
Burlington, CT, 06013

About: Hello! My name is Aislyn, I have been taking care of dogs professionally for 6 years now. I have worked as a walker/sitter since 2017, and have worked in all types of doggy daycares (I’ve handled 50 dogs at one time- whew!) I also have experience as an animal transporter, delivering dogs across the country via ground transport and airline cargo! I have experience with ALL types and temperaments of dogs, from hyperactive puppies to senior special needs dogs. I am well versed in medication administration and special care, as well as some basic positive reinforcement training. I am currently doing rover full time, so all of my availability is open to providing the most care and attention to your fur family! I understand that a huge level of trust is needed between clients and their dog walker. I am always available to answer any questions or concerns you may have before or after booking with me. Since I've worked in this industry for many years, I have a lot of knowledge of proper dog handling and safety procedures. Dogs will NEVER be off leash outside of their own fenced in yard or closed run (with clients permission) and I am always alert and evaluating potential dangers outside of the house while walking (other dogs, people, etc). As a dog sitter, I am trusted with many keys/gate codes and always follow specific procedures given by clients to enter and lock up their houses. I have leash attachments for my car seatbelts, seat covers, and a soft “gate” between my backseat and front seats in order to transport dogs safely. If you have any questions, please message me and I will be happy to answer. (Also message me if you'd like to see my comprehensive resume!)

Sitter Profile Image: Taylor B.
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Taylor B.
from
$20
per walk
10 years of experience
New Hartford, CT, 06057

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!

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The median cost per walk for dog walking in Winchester is $22

Dog parents share their Rover experiences - Winchester

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5.0 out of 5 stars

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!

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Rachel C.
Dog Walking
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Popular requests for dog walking - Winchester

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Sitters in Winchester average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester

Frequently asked questions about Rover

As of August 2026, there are 1,570 sitters on Rover offering Dog Walking across Winchester. 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 Winchester. 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 Winchester.

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 Winchester. On Rover:

  • 98% 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.

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