Dog Walking Cheshire

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

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Over 33
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Cheshire, 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: 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

“Happy Fourth of July Kelly thanks for all you do”

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Christopher J.
Sitter Profile Image: Darya H.
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Darya H.
Star Sitter
from
$21
per walk
5.0 out of 5 stars
• 13 reviews
5 repeat clients
10 years of experience
Prospect, CT, 06712

“Darya is always on time, always accommodating to my changing schedule as a medical professional, and always so sweet with my dog Wally. As a rescue, Wally tends to be suspicious of strangers when first meeting them. But when he first met Darya, he approached her with ease. I like to believe this is a testament to Darya’s positive aura. We are so glad we found her!”

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Breanna C.
Sitter Profile Image: Sara R.
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Sara R.
from
$18
per walk
5.0 out of 5 stars
• 12 reviews
5 repeat clients
10 years of experience
Prospect, CT, 06712

“Sara was awesome!! She came literally with an hour notice and my dog enjoyed her walk with her. Definitely recommend & will book again in the future. Thank you!”

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Lusianna M.
Sitter Profile Image: Rebecca F.
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Rebecca F.
from
$25
per walk
5.0 out of 5 stars
• 29 reviews
12 repeat clients
20 years of experience
Wallingford, CT, 06492

“We don’t have a very easy dog to walk but Rebecca did a great job making him feel comfortable and get plenty of exercise and time outside! She gave us great feedback on ways to help in the future with a scared stressed dog and we will definitely have her walk our dog in the future!”

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Michael D.
Sitter Profile Image: Brooke P.
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Brooke P.
from
$30
per walk
5.0 out of 5 stars
• 1 review
1 repeat client
15 years of experience
Cheshire, CT, 06410

“Brooke is amazing!!! She is very kind, gentle, and those just how to handle my puppy who’s not a puppy. Thank you so much. I’m lucky to have you.”

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FJ U.
Sitter Profile Image: Kelly R.
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Kelly R.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
2 repeat clients
12 years of experience
Meriden, CT, 06451

“Kelly was a great communicator on any slight changes needed to our walking schedule, and did an excellent job adapting to our middle aged dog's long and sniff filled walks. She also checked in about bringing her young (human) kiddo on the walks, which was exciting for us to make sure our dog will be used to strollers and kids for future walks. Highly recommend!”

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Corey W.
Sitter Profile Image: Amanda & Scott H.
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Amanda & Scott H.
from
$30
per walk
20 years of experience
Cheshire, CT, 06410

About: We’ve had family dogs since childhood — and have provided trusted pet care to friends and neighbors for 20+ years. Our own rescue pup who was part of our family for many years recently passed. We’d love to help ensure your pet is well cared for when you’re out and about — with with walks, check ins, or sitting, as needed! We’re here for all of your pup’s needs, complete with lots of walks and attention throughout the day! We’re available daily, on weekdays and many weekends—and can work with you re: any specific scheduling needs. We’ll find the best walk and play spots near your home to give your pup plenty of time outdoors, exploring, finding smells, and socializing with other dogs (if preferred).

Sitter Profile Image: Mikenna R.
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Mikenna R.
from
$20
per walk
5.0 out of 5 stars
• 5 reviews
2 repeat clients
7 years of experience
Hamden, CT, 06518

“Mikenna was prompt, courteous and did an amazing job taking care of my pups. Highly recommend 🙂”

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James W.
Sitter Profile Image: Alex K.
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Alex K.
from
$28
per walk
5.0 out of 5 stars
• 45 reviews
18 repeat clients
10 years of experience
Berlin, CT, 06037

“Alex had great communications and provided timely updates with photos of our pup. Will definitely be utilizing her services again”

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Aime B.
Sitter Profile Image: Sadie R.
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Sadie R.
from
$30
per walk
5.0 out of 5 stars
• 11 reviews
4 repeat clients
15 years of experience
Plantsvile, CT, 06479

“Sadie is our go to sitter. She’s so sweet and kind and nice to the dogs. Thanks Sadie! 💕💕💕”

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Deb J.
Sitter Profile Image: Tiffany C.
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Tiffany C.
from
$30
per walk
1 repeat client
20 years of experience
Hamden, CT, 06518

About: Hi, my name is Tiffany, and I recently moved into the neighborhood. I wanted to take a moment to introduce myself and share a bit about what I do. I am an animal rescuer and a Connecticut-licensed wildlife rehabilitator, and I also offer dog walking and in-home pet sitting services. Animals are truly my passion, and I would love the opportunity to care for your furry family members. We also offer pet waste removal services for your yard. I work from home and dedicate my life to the care of pets of all species. This is my passion. I am very flexible and will take care of your baby as though they are my own. I have a large fenced in yard. I have a safe home. I also am available to take care of any pet within their own home as I know this is the most comfortable and stress-free for your fur baby.

Sitter Profile Image: Jordan S.
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Jordan S.
from
$25
per walk
5.0 out of 5 stars
• 32 reviews
10 repeat clients
5 years of experience
Hamden, CT, 06514

“Kirby loved Jordan!! So excited to have her take care of him!”

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Michael S.
Sitter Profile Image: Liana P.
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Liana P.
from
$17
per walk
10 years of experience
Southington, CT, 06489

About: I have had pets since I was a baby. I had two rabbits who I took care of during my childhood, such as feeding and brushing. When I was around 10 years old we adopted my current dog, who I walk and play with frequently. My family often petsits other animals as well, mostly dogs. I have helped with catering to these dogs needs since I was 9 and have always loved getting the opportunity to take care of them! These experiences have taught me the responsibility necessary to actually take care of animals. I am available to pet sit the entire week except on Mondays. I am a very flexible person and do not mind cancellations or late notices. I have a large yard my dog loves to play in, along with The Canal Trail as a 2 minute walk away from my house. I often take toys from our large toy box to go out into the yard and play with him.

Sitter Profile Image: Ashley G.
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Ashley G.
from
$30
per walk
4.9 out of 5 stars
• 81 reviews
34 repeat clients
2 years of experience
Southington, CT, 06489

“Ashley is really great with my dogs. She took them in a solid walk and made sure they had plenty of water and treats before she left. I'd highly recommend her for you pups!”

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Natalie C.
Sitter Profile Image: Thomas O.
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Thomas O.
from
$22
per walk
20 years of experience
Wallingford, CT, 06492

About: I have over two decades of experience working with and caring for dogs of many different backgrounds, personalities, and needs. One of my greatest learning experiences has been caring for my own dog throughout every stage of his life. When he was younger, he was energetic, intelligent, and full of personality, and as he has gotten older and lost his vision in both eyes, I’ve learned how to adapt my care to meet his changing needs. I have experience administering medications, providing senior care, and creating safe, comfortable environments for dogs with special needs. My hands-on experience has taught me the importance of patience, consistency, and understanding that every dog is unique. I strive to make every dog in my care feel safe, loved, and comfortable, no matter their age or individual needs. I have a very flexible schedule and am available most weekdays! Wednesdays and most Sundays are my only regular days of unavailability. Please don’t hesitate to reach out with your booking request, as I may be able to accommodate your needs. I prioritize creating a safe, comfortable, and loving environment for every dog in my care. I have personal experience caring for my own elderly, blind dog, which has taught me the importance of maintaining a safe space, being patient, and adapting to each dog’s unique needs. I’m also experienced in administering medications and caring for dogs with special needs. My goal is to ensure every pet feels secure, comfortable, and well cared for, with plenty of attention, affection, and care tailored to their individual needs.

Sitter Profile Image: Melinda R.
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Melinda R.
from
$22
per walk
5.0 out of 5 stars
• 144 reviews
52 repeat clients
10 years of experience
Berlin, CT, 06037

About: Hello! I am so happy you clicked on my profile! Please sniff around! We treat every stay whether your pet is big or small, meows or barks - as a vacation of their own!! We tailor their needs and work around their schedules to keep their routine as similar as possible to make an easier adjustment. My love for animals has always been my biggest passion! Although I love them all, my biggest love is for senior animals or animals with disabilities. I have been fostering dogs and cats for over 6 years now and focus mostly on paralyzed dogs, senior dogs, and even ‘fospice’ dogs, dogs who may have a limited amount of time left on this planet but it's truly an honor to give them all the love and being there the whole way. Outside of doing Rover: I am a nanny for 2 legged children, and I also work at an animal veterinary hospital. I am very comfortable taking care of your animals with any special needs they may have! I am happy to make any accommodations they may need, please just ask! My schedule is very flexible! Thank you for giving me the time to show you that you have picked the right sitter! I will update you as much as you would like, with many pictures of your fur-baby (s). I do have dogs of my own- but can accommodate if you would prefer your animal(s) to be separate from mine *** We only have 3 pets- Henry, Betty, and Timber. The rest were fosters we were taking care of. We’re having an issue updating it on my profile!*** I do not discriminate* any breed, small or large I am happy to walk, house sit, board, or do a drop in visit! As a passionate and experienced pet sitter, I offer personalized, high-quality care that goes beyond the basics. What sets me apart is my deep love for animals, combined with my commitment to providing individualized attention for each pet. Whether it's following specific routines, administering medication, or simply offering companionship, I ensure every pet feels safe, loved, and comfortable. With professional certifications in pet first aid and years of hands-on experience, I prioritize your pet’s well-being and am always prepared for any situation. Communication is key, **While I may not be able to respond to a new request right away as I can not be on my phone at times, when your pet is in our care I provide regular updates, including photos and videos, so you can rest assured knowing your pet is in the best hands** I offer flexible scheduling and tailor my services to meet the unique needs of each pet. From daily visits to overnight stays, I am here to give your furry family member the attention they deserve when you can't be there. Let me be your pet’s second-best friend! Let me give you a brief description of what their stay will be entailed of: My boyfriend and I have opposite work schedules, He works during the day and I work night shifts, giving me the flexibility to be home and love and care for your pet(s)! • On a typical day we will begin our mornings going for a walk (we live on a quiet dead end street that enters a park.) Then breakfast will be handed out and always fed separately from our dogs. Water of course is always fresh and always provided in multiple places within the house and on our deck. We have a dog door that the dogs are more than welcome to use that leads out to our deck and leads down to our fenced in area. Our home is filled with plenty of dog beds, blankets, and tons of toys! (Toys, dog beds, and blankets are always washed at the end of each stay.) You are more than welcome to bring any comfort items for your pet’s stay that will be of course laid out for them. • Updates are always provided with pictures/videos during their stay! I will always let you know how your pet(s) are doing while in our care and provide you with my personal number as well. • Your pets are welcomed on our furniture and do not have restrictions, unless you specifically ask them not to. We will be more than happy to accommodate to their needs and any schedule you will like them to stick to. • The items we do ask that you bring is their dog food, any medications, and written instructions you may have, lastly their vet information and emergency contact if you have one. • We have 2 acres and use long leads outside the fenced in area to play outside! Your pet(s) will always be watched and cared for, have plenty of outside time, as well as play time! • We always end our night with a short walk before bed and your pet(s) are welcomed to sleep where they are most comfortable! I have a an area in our backyard that is fenced in. We live on two acres or land that your loved one(s) can have access to and enjoy. I am happy to take them for many walks throughout the day as well I am happy to accommodate to your pets needs and will follow any directions you may have for your pet(s)

Sitter Profile Image: Elizabeth L.
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Elizabeth L.
from
$25
per walk
5.0 out of 5 stars
• 24 reviews
4 repeat clients
3 years of experience
Naugatuck, CT, 06770

“Elizabeth is an amazing dog walker! She takes my dog on a 30 minute walk, plays with him, makes sure his water is filled, and is on time. I am so glad I found her for my dog!”

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Kayla R.
Sitter Profile Image: Alessia D.
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Alessia D.
from
$25
per walk
2 years of experience
Hamden, CT, 06514

About: I am trustworthy and will always put the dogs needs that I am sitting first. I will always make sure the dog I am with is happy and has everything he/she needs. I currently work a part-time job, so I have a good amount of free time during the week to be able to help and provide pet care for others. I’ve been on rover for 2 years now and have a dog of my own. I really enjoy spending time with dogs wether it’s walking them or just being able to play and spend time with them.

Sitter Profile Image: Billie-Jean S.
Verified Enhanced Background Check
Billie-Jean S.
from
$20
per walk
5 years of experience
Watertown, CT, 06779

About: I have years of hands-on pet care experience, starting with caring for family dogs and continuing professionally at a doggy daycare. I work with dogs of all sizes, energy levels, and temperaments, ensuring safe play, proper routines, and individualized attention. As a dog owner myself, I understand the trust involved in pet sitting and treat every dog with patience, consistency, and care. I can do Mornings from 5:30 or 6am to 11am, I work from 12-6 pm so after work I can do 6:30pm-whenever is needed. from Monday-Friday. Weekends I can do anytime. I always make sure that the pets are safe, are always feed, always have water, and I take them out on walks very frequently. If the parents are ok with it I also like to take them to dog parks to learn socialization and to be able to run around and have fun without possibly breaking anything in the house.

Sitter Profile Image: Kyara F.
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Kyara F.
from
$25
per walk
5.0 out of 5 stars
• 1 review
3 years of experience
Waterbury, CT, 06708

About: As someone who knows that your pet is a part of your family, you can trust that I will do my absolute best to take care of them. I have been a pet sitter for 4 years, providing exceptional care to the pets of neighbors, family, friends and clients. I have experience caring for pets with special needs, dietary restrictions, and medication. I’m currently working full time, but I’m available for overnights with any pet! I’m okay with traveling the distance to your house to watch your pet as well as house sit if needed! I understand that animals feel most comfortable around familiar surroundings, and wouldn’t want to displace them. I’m very flexible, just let me know when I’d be needed. The environment will be your own home. Your pet will not feel displaced, and will remain comfortable in his or her own bed. I understand that familiarity is key when owners are away.

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The median cost per walk for dog walking in Cheshire is $23

Dog parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Ally was amazing, she walked my golden. So responsible and friendly. I would hire her again in a heartbeat! Thank you Ally 🥰

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Alyson A.
Dog Walking
5.0 out of 5 stars

Brooke is amazing!!! She is very kind, gentle, and those just how to handle my puppy who’s not a puppy. Thank you so much. I’m lucky to have you.

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FJ U.
Dog Walking
5.0 out of 5 stars

Lori was very loving and attentive to my Nala, spent time with her and sent pictures. Nala was very happy with her and so was I

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Ann B.
Dog Walking
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How to book dog walking

  1. 1. Search

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

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Popular requests for dog walking - Cheshire

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Sitters in Cheshire average 3
repeat dog walking clients

FAQs for Dog Walking - Cheshire

Frequently asked questions about Rover

The average cost of Dog Walking in Cheshire is $20 per walk as of October 2026. Most bookings cost between $17 and $34 per walk. On Rover, 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 2,817 sitters on Rover offering Dog Walking across Cheshire. 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 Cheshire. 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 Cheshire 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 Cheshire. On Rover:

  • 89% of walkers can help with special care needs
  • 91% can help with giving oral medications or injections
  • 96% 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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