Dog Walking Winsted

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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.

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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
8 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: Karina & Jared S.
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Karina & Jared S.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
• 143 reviews
64 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: Theresa C.
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Theresa C.
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: Thomas B.
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Thomas B.
from
$17
per walk
4.8 out of 5 stars
• 8 reviews
3 repeat clients
6 years of experience
Avon, CT, 06001

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.

Sitter Profile Image: Tara W.
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Tara W.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 10 reviews
4 repeat clients
1 year of experience
Weatogue, CT, 06089

“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.”

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Colin P.
Sitter Profile Image: Shianne E.
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Shianne E.
from
$20
per walk
7 years of experience
West Hartford, CT, 06107

About: I’ve loved dogs my whole life! I’ve been in the animal care industry for about 7 years now ! Working in Kennels, Vet Clinics, volunteering at the animal shelter when I was younger and now I’m a dog groomer (3years). I have lots of experience with many breeds and sizes! No dogs too big or too small! I can trim nails if needed or even offer you my services as a dog groomer :) I’m currently working full time but I am a dog groomer so I have a pretty flexible schedule. Thursday and Sundays I’m available any time ! Monday-Wednesday I would be available after 2pm. Friday and Saturday availability is after 1pm. I am big on affection! I love to cuddle up with my cat (Sauce) and yours! If you’ll give me a chance ! I love to hike and be outdoors! I have a dog named Daisy Mae and she’s always been a fan of taking trips to the creek or just taking hours long walks just sniffing everything she sees! I make sure she’s tick free when we finish especially! I am a very outgoing person and very patient when it comes to really everything! I will make sure to treat your doggie just like mine with lots of love and extra attention! I tend to get along with bigger dogs a lot because they are high energy and love to get out and move !

Sitter Profile Image: Kelsey L.
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Kelsey L.
from
$25
per walk
5.0 out of 5 stars
• 27 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: Priscilla E.
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Priscilla E.
from
$20
per walk
5.0 out of 5 stars
• 14 reviews
2 repeat clients
20 years of experience
West End, Hartford, CT, 06105

“Priscilla saved the day accepting my request at very short notice. I had a 12 hour shift to work and no coverage for Louis. Additionally, I realized at the end of that 12 hour shift that I had no coverage for the next two days due (in no small part to a massive house move that had just occurred). Again, Priscilla came to the rescue and helped me for the next two days. She is a great communicator and a clearly dedicated professional.”

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Anne F.
Sitter Profile Image: Nora E.
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Nora E.
from
$35
per walk
5.0 out of 5 stars
• 2 reviews
15 years of experience
Granby, CT, 06035

“Nora was very patient with my finicky dog. She did not give up on him when he had a hard time adjusting!! Thanks Nora.”

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Sharon Baj 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: Erica T.
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Erica T.
from
$45
per walk
5.0 out of 5 stars
• 18 reviews
7 repeat clients
8 years of experience
Bloomfield, CT, 06002

“Very good with my dog I do recommend”

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Patty M.
Sitter Profile Image: Elizabeth F.
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Elizabeth F.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Newington, CT, 06111

“Elizabeth was amazing! She helped us out incredibly last minute and took amazing care of our pup while we were out for the day longer than expected. Thank you so much, Elizabeth!”

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Laura & Nick S.
Sitter Profile Image: Selina M.
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Selina M.
from
$18
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
New Britain, CT, 06053

About: I have had both cats and dogs and love giving them attention and the time they need outside. Being able to give them the energy release they need is my job and the extra cuddles and treats are just a bonus! I currently am a college student and have long breaks where I love to spend time walking and sitting dogs whenever I can. I am free on most holidays and during the summer since I live so close to home. I keep a close eye on pets when I dog sit and love to spend all my time with them whether it's on the couch getting extra pets or going outside or the backyard to play.

Sitter Profile Image: Collin B.
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Collin B.
from
$15
per walk
4.9 out of 5 stars
• 10 reviews
4 repeat clients
30 years of experience
Longmeadow, MA, 01106

“Collin was great! Super punctual, arrived on time, great communication. Always a pleasure to have him walk Molly!”

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Dylan K.
Sitter Profile Image: Annie D.
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Annie D.
from
$38
per walk
5.0 out of 5 stars
• 95 reviews
27 repeat clients
10 years of experience
South Windsor, CT, 06074

“Wonderful service”

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Andre S.
Sitter Profile Image: Victoria C.
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Victoria C.
from
$30
per walk
5.0 out of 5 stars
• 1 review
15 years of experience
Enfield, CT, 06082

About: I have always had a pet dog and ever since I was a teenager, I’d dog-sit for family and neighbors. Since college, I’ve been pet-sitting ajd dog walking on a more professional level. I’ve babysat for a few hours, simply for a walk, but have also watched multiple high energy dogs for up to two weeks. I’ve cared for dogs under a year old and up to 13 years old. I’ve always loved dogs and find them very easy to get along with and care for no matter their size, age, or personality. I have also cared for kittens a few weeks old, senior cats, administering medication orally, grooming them if they have long hair etc. Cats have a very different energy than dogs but I enjoy taking care of them just as much as dogs. I am currently in between jobs so I have a lot of free time to care for other dogs, whether it is a short walk or a multi-hour play date, etc. I always follow whatever guidance I am provided by pet parents. This means if you are only comfortable with your dog on a leash or lead while in your yard, I strictly follow that. If there are specific commands to use, certain behavior to watch out for or discourage, particular toys or activities they enjoy, I always follow what information I am given and am always open and communicate well about any issues or concerns that might arise on my end.

Sitter Profile Image: Anna C.
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Anna C.
from
$25
per walk
5.0 out of 5 stars
• 21 reviews
9 repeat clients
20 years of experience
East Longmeadow, MA, 01028

About: Dogs have and will always be a huge part of my life. We got our first family dog when I was just 3 years old and the rest is history. My husband Jack is extremely passionate about animals as well and is my partner in all of this so you get two dog sitters for the price of one. Between the two of us your pet will get so much love, cuddles & exercise. We guarantee a level of attention and care that I feel confident your pet won’t get anywhere else; between this and Rover taking it’s fee our prices might be on the high side but they reflect our level of personalized and professional level of care. I also just want to add that our love for dogs extends to all animals so cats etc are all welcome to come hang with us :) Important Note: if you are reaching out for house sitting my husband and I only take those if we both are allowed to stay the night. We prefer to do this for safety as well as enabling the best care possible for your pet. Your pets will be my top priority & my main focus when they stay with us! I feel pretty confident that they will get more quality time, attention & lovin with me then any other pet sitter! I have a smoke free home and do not have any dogs currently living at my house so your pets will be my only focus! Also a child free home!

Sitter Profile Image: Yvonne D.
Verified Background Check
Yvonne D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 4 reviews
2 repeat clients
20 years of experience
southbury, CT, 06488

About: Hi! I enjoy meeting, engaging with, and caring for family pets and have experience with all breeds of dogs and cats at all age ranges. I am available for ongoing long-term set schedules as well as flexible schedules for pet sitting. My schedule allows me to check in morning, midday, and/or late afternoons/evenings. I do not presently render services at my home, but I do not mind crating your dog at your home and enjoying many walks and hikes nearby.

Sitter Profile Image: Janice A.
Verified Enhanced Background Check
Janice A.
Star Sitter
from
$45
per walk
5.0 out of 5 stars
• 283 reviews
81 repeat clients
35 years of experience
RHINEBECK, NY, 12572

“Janice is super responsive and great with my large dogs - she’s a master at handling them and always shares relevant info after walks if needed.”

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Corrine P.
Sitter Profile Image: Brenna B.
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Brenna B.
from
$35
per walk
5.0 out of 5 stars
• 7 reviews
1 repeat client
12 years of experience
Pittsfield, MA, 01201

“Brenna did a great job. She loves dogs & doing this donit is a win-win. Of course we recommend her.”

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Betts M.
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The median cost per walk for dog walking in Winsted is $22

Dog parents share their Rover experiences - Winsted

1 / 1
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!

Profile image
Rachel C.
Dog Walking
5.0 out of 5 stars

Stacey is genuinely the BEST! Person to person, she is so kind, responsive, and easy to work with. Stacey with dogs is even better!!! Blue LOVES Stacey and gets well taken care of every time Stacey visits! I recommend her 110%

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Rachel C.
Dog Walking
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  • 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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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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 of Dog Walking in Winsted on Rover is $28 per walk as of October 2026. Most bookings cost between $28 and $39 per walk. walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,691 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 bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Winsted after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the 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 , 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 .

Yes, you can find walkers who have experience with handling special pet needs in Winsted. On Rover:

  • 90% of walkers can help with special care needs
  • 92% can help with giving oral medications or injections
  • 97% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .

walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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