Dog Walking Winchester Center

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Winchester Center, 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.

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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: Zoe G.
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Zoe G.
from
$25
per walk
5.0 out of 5 stars
1 review
1 repeat client
7 years of experience
Torrington, CT, 06790

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

Sitter Profile Image: Katie O.
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Katie O.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
23 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: Rachael R.
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Rachael R.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
12 reviews
6 repeat clients
20 years of experience
Middlebury, CT, 06762

Rachael was incredible! Super flexible, always on time, and knew how to care for our dogs. It’s hard to find someone willing to care for our big babies but she rose up to the challenge. She is always super detailed in how the walks go and keeps us informed about anything that we should know about. We highly recommend Rachael, super polite and responds super quick! Our dogs absolutely loved her, we will definitely be booking again when we need a dog walker. Thank you Rachael!

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Chasidy R.
Sitter Profile Image: Kailah J.
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Kailah J.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
11 reviews
6 repeat clients
3 years of experience
Waterbury, CT, 06706

Great walker. Showed up on time and was great with Rosie

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Sarah L.
Sitter Profile Image: Tara N.
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Tara N.
from
$25
per walk
5.0 out of 5 stars
30 reviews
13 repeat clients
25 years of experience
Torrington, CT, 06790

Tara is extremely reliability and did so great with our high energy pup! Highly recommend.

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Sebastian & Elayna R.
Sitter Profile Image: Priscilla E.
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Priscilla E.
from
$20
per walk
5.0 out of 5 stars
13 reviews
2 repeat clients
20 years of experience
West End, Hartford, CT, 06105

Priscilla is awesome. Our dog is very nervous with people and this is the fastest she has gotten comfortable with someone new. She takes great care of our dog and our dog always comes back happy after walks!

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Jacquelyn W.
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

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!

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Kaila S.
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: Michelle T.
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Michelle T.
from
$30
per walk
4.9 out of 5 stars
132 reviews
57 repeat clients
6 years of experience
New Britain, CT, 06051

Highly recommend very sincere sweet and patient. You’re dog and home are in great hands with michelle.

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Richard M.
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: Ashley A.
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Ashley A.
from
$18
per walk
4.9 out of 5 stars
42 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: Morgan D.
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Morgan D.
from
$17
per walk
5 years of experience
torrington, CT, 06790

About: What started as a personal challenge—overcoming my childhood fear of dogs—became a journey of love. By volunteering with service dogs, I discovered my passion for all kinds of dogs, big and small. Now, I bring that same warmth and dedication to caring for your pet. My Schedule is Flexible, Reliable, and Full of Love for Your Fur Babies! I work part-time, so I have plenty of time to dedicate to your pets. Most weekdays are wide open for visits, playtime, or overnight stays. Whatever your furry family member needs to feel happy, safe, and loved-i'm your sitter! Anxious or rambunctious, I'm patient and caring. Let’s make sure your pet gets the attention and care they deserve!

Sitter Profile Image: Jacqueline C.
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Jacqueline C.
from
$25
per walk
2 years of experience
Torrington, CT, 06790

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.

Sitter Profile Image: Andrea R.
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Andrea R.
from
$25
per walk
4.9 out of 5 stars
66 reviews
32 repeat clients
6 years of experience
Newhallville, New Haven, CT, 06511

Andrea was so great to communicate with - she sent lots of videos and was clearly so sweet with our dog. Very happy to have connected with her, and highly recommend!

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Erika S.
Sitter Profile Image: Elissa U.
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Elissa U.
from
$20
per walk
5.0 out of 5 stars
6 reviews
9 years of experience
Canton, CT, 06019

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.

Sitter Profile Image: KELLY G.
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KELLY G.
from
$22
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
30 years of experience
Meriden, CT, 06450

Thanks for all you do!

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Christopher J.
Sitter Profile Image: Meaghan G.
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Meaghan G.
from
$30
per walk
5.0 out of 5 stars
19 reviews
8 repeat clients
10 years of experience
Harwinton, CT, 06791

About: I’ve cared for many different animals throughout my life, including mammals, birds, reptiles/amphibians, exotics, farm animals, and wildlife. I’ve cared for pets of friends and family. I have experience with overnight sitting in the pet’s home. I also have experience caring for senior and special needs animals. I spent 6 months as a volunteer at a vet clinic assisting with exams and surgical procedures, and I am currently exploring career paths in animal sciences and wildlife rehabilitation. I have lots of availability to care for your fur babies! I work part-time as a waitress while exploring different careers in the field of animal behavior and sciences. I have the flexibility to accommodate to your schedule and needs. I can be available on most weekends and holidays. I also accept same-day bookings. I prefer to care for animals in their own home where they feel most comfortable. As well as walking in areas they are familiar with. I always make sure to maintain pet safety in the home such as keeping doors/windows/gates shut and keeping hazardous items and toxic plants out of reach or locked away.

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: Jonathan H.
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Jonathan H.
from
$20
per walk
30 years of experience
Thomaston, CT, 06787

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.

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

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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Winchester Center

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winchester Center average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester Center

Frequently asked questions about Rover

As of September 2026, there are 1,541 sitters on Rover offering Dog Walking across Winchester Center. 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 Center. 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 Center.

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 Center. On Rover:

  • 98% of walkers can help with special care needs
  • 96% 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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