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

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

“⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.”


“Sherry took our menagerie of dogs and cats in stride when she arrived and she handled my dog Duncan with ease during the walk. She obviously loves animals and my dog, who is sometimes shy with strangers, immediately liked her and will be happy to see her the next time she comes. I highly recommend her if you need a good caretaker for your pets.”


“Just wonderful, haven’t been able to meet up yet,(work work work )however very wonderful communication and updates she comes to let my my pup out and give her a little energy release on my 12hr shifts. Quick responses and overall feelings of trust with a person coming into my home! She even makes sure to tell me what my cat was up to when she visits. Nothing but great experiences with her!”


About: I’ve been caring for pets since I was a teenager. Whether it be my own dog or someone else’s, I love taking care of animals. In the past, I’ve spent extensive time caring for the pets of friends and neighbors along with my own. I work as a freelancer, so I can make my schedule work for any times! While I am available on weekends, I focus on M-F from 8am-8pm for pet sitting. With my own dog, I’m very protective and make sure she is safe and gets the care she needs. That is no different with other dogs. Whenever I’m watching a pet, I always make sure to keep them safe and give them the best time!

About: Friendly animal lover! I have always had a dog, cat, or multiple animals since a young age! Currently have 2 dogs (rescues). Very polite and easy to work with. I work from home so I am flexible during the day and evenings too accommodate schedules. Love taking walks so would love to have a companion! I take pride in providing the best care to your pets. I am a clean person and would always leave your home as I found it or better. Also happy to provide updates via notes or texts!

About: I cared for my family dog for 12 years until she passed, as well as cared for my family and friends furry animals over the years. I’m currently working full time. Can be available before 10:00-11:00 am and in evening after 6:30pm or 7:30pm. Work schedule rotates, and can be flexible. I’ll make sure they are safe at all times, and well taken care of. Take them on walks, feed them if needed, and play of course!

“Our doodle and 2 kitties love Kyla! One of these kitties is very shy with people. When Kyla comes over though he comes out to look for her! Kyla is a natural with our pets and we feel lucky we found her.”


About: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!

“Christopher and Leslie are professional, they're skilled at handling dogs, and my dogs love them. Even our two very shy dogs warmed up to them quickly. (And my cats, who were not part of the booking, also were happy to say hi to them. They're obviously cat people, too!) They were happy to accommodate some last-minute changes to the bookings, which I appreciated very much. I will definitely book them again when I need help.”


About: With 15 years as a veterinary technician and hospital manager, plus several years managing a doggie daycare and boarding facility, I’ve had the joy of caring for pets of all kinds—birds, ferrets, cats, dogs, and even fish. I’m passionate about making each pet’s care personal and comfortable, treating them like family while giving you peace of mind. I’d love to help ensure your beloved companion gets the attention, love, and care they deserve. I'm currently available full time for pet care and walks and will have plenty of time for the care you need for your fur babies. I will follow all instructions left by you to properly care for your animals in your home and make plenty of time for cuddle sessions too.

About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)

“My dog is very cautious around new people and Shaghayegh has been wonderful with him! She has taken time to get to know his quirks and listened carefully to all recommendations and instructions I have given her in regards to and how to deal with his shyness. She clearly loves dogs and really makes an effort to make their experience enjoyable when they are with her. I highly recommend her!”


About: I have been an animal lover & owner my entire life. I've always had a dog along with the occasional hamster, cat, guinea pig, lizard, hermit crab, rabbit, bird & fish. I love animals especially dogs. I am very comfortable with large breed dogs as well as smaller dogs too. I like to think the bigger the dog the more loves & cuddles you get.🥰 I've volunteered for rescues over the past 10 years & have fostered both dogs & cats. I'm very excited to meet new animals and their owners. I currently have 1 dog & 3 cats. I try to stick to your animal's schedule so they continue with their normal routines. I make sure your animal is given lots of attention & play time. I will show your animal affection & lots of play time & snuggling if they enjoy that. I've never met a dog that hasn't liked me....big or small.

About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions

About: Hi, I'm Audrey I'm a lifelong dog lover with two family pups — Elvis, a 3 year old Italian Mastiff, and Bella, a 13 year old sweet senior Shih Tzu-Maltese mix. I'm experienced with both energetic puppies and older dogs who need a gentler touch. Whether your dog loves long walks or slow strolls, I’m here to give them the care and attention they deserve! I work part time, so my schedule is flexible. I am available for drop ins, and walks throughout the day. I’m here to give your pup company or playtime! I do not have capability to board dogs. I offer drop ins, and routine walks that fit your schedule. I am able to give medications, food & treats, and extra love!

About: I have owned and trained dogs most of my life, grew up on a farm with all types of pets and find it second nature to treat them like family. I currently work from home and have a very flexible schedule. I can house sit, drop in or stay with your pet as long as you need someone. My dog has a fenced in yard and is at day care for socialization M-F so I can have my full attention on your dog. I currently work from home part time so I have plenty of time for your pet! I am awake early and have a flexible schedule to fit yours. I make sure you and your pet are comfortable with me and follow instruction when caring for your pet. You know your pet best and I want them to be happy and content with me.
Loving dog walkers in your neighborhood
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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Hannah D.Star Sitter

“⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.”


Alexsys T.Star Sitter

“Alexsys is awesome. Communicative, thorough, and sends me all the updates and photos I need when I’m away. She even sent a picture of my porch kitty!”


Sherry R.

“Sherry took our menagerie of dogs and cats in stride when she arrived and she handled my dog Duncan with ease during the walk. She obviously loves animals and my dog, who is sometimes shy with strangers, immediately liked her and will be happy to see her the next time she comes. I highly recommend her if you need a good caretaker for your pets.”


Kimberly B.Star Sitter

“Just wonderful, haven’t been able to meet up yet,(work work work )however very wonderful communication and updates she comes to let my my pup out and give her a little energy release on my 12hr shifts. Quick responses and overall feelings of trust with a person coming into my home! She even makes sure to tell me what my cat was up to when she visits. Nothing but great experiences with her!”


Gabriel K.
“Gabriel is everything you would want from a pet sitter. Responsible, caring, reliable, playful, punctual, communicative, etc. I would Highly recommend him for any of your pet sitting needs. I will be using him again as I know many others will as well. So, book him now before he gets too busy!!!!”


Meghan H.

“Meghan is great with my pups! She does her best to take care of them and is flexible when late minute things pop up!”


Charissa L.
“Charissa is a very responsible dog sitter. She takes care of our two labs for us. She is sure not to just feed them, but spend time with them and play ball with them in the backyard. She also takes them for walks as needed. Our dogs are always excited to see Charissa. And enjoy her company.”


Courteney B.
“Courteney is great with all animals, and has a huge heart when it comes to caring for animals. She has always taken great care of my three dogs.”


Kyla P.Star Sitter

“Our doodle and 2 kitties love Kyla! One of these kitties is very shy with people. When Kyla comes over though he comes out to look for her! Kyla is a natural with our pets and we feel lucky we found her.”


Allison B.
“Allison is very dependable, never calls out or leaves you hanging for a commitment. Allison shows respect to peers, adults and customers. Allison would be perfect for this position with Rovers due to her love of animals. Allison's smile is infectious. Thank you, Janet Miller Marketing Manager Atomic Trampoline Park”


Christopher P.

“Christopher and Leslie are professional, they're skilled at handling dogs, and my dogs love them. Even our two very shy dogs warmed up to them quickly. (And my cats, who were not part of the booking, also were happy to say hi to them. They're obviously cat people, too!) They were happy to accommodate some last-minute changes to the bookings, which I appreciated very much. I will definitely book them again when I need help.”


Katie R.
“I have known Katie for more than a decade and have worked with her in pet-related fields in a number of environments. I say without reservation that she is one of the most compassionate, responsible, caring individuals I have known and is completely committed to doing what is best for any animal in any situation. I would trust her with my pets in a heartbeat, as can anyone.”


Sophia C.
About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)


Shaghayegh H.
Star Sitter


“My dog is very cautious around new people and Shaghayegh has been wonderful with him! She has taken time to get to know his quirks and listened carefully to all recommendations and instructions I have given her in regards to and how to deal with his shyness. She clearly loves dogs and really makes an effort to make their experience enjoyable when they are with her. I highly recommend her!”


Kathy G.Star Sitter
“Kathy has care for our family dogs Gunter boxer, and Ellie yellow lab for several years. We also have employed her to house sit. Kathy is very conscious and trustworthy. Our family highly recommends her to care for your pets too.”


Mark R.

“The BEST. Patient,kind and reliable..Highly recommended.”


DaVion P.
About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions


Audrey B.
“I can’t recommend Audrey B. enough as a pet sitter and dog walker! She is one of the most compassionate, responsible, and attentive people I know—especially when it comes to animals. Audrey has a natural ability to connect with pets and treat them like family. Whether it’s a playful pup or a shy senior cat, she’s always patient, gentle, and tuned in to their needs. I’ve seen firsthand how much love and care she puts into every interaction, from long walks to cuddles on the couch. She’s the kind of person who notices the little things—if your dog seems a little off or your cat needs some extra attention, Audrey will catch it and respond with care. Plus, she’s incredibly reliable and communicative, so you’ll always know your pet is in safe hands. If you’re looking for someone to care for your pet like you would, Audrey is absolutely the one to call. Your furry family members will be in the best hands!”


courtney b.

“She was fantastic. Both my boys like her I would recommend her to anyone with any size dog.”


Alex M.
About: I have owned and trained dogs most of my life, grew up on a farm with all types of pets and find it second nature to treat them like family. I currently work from home and have a very flexible schedule. I can house sit, drop in or stay with your pet as long as you need someone. My dog has a fenced in yard and is at day care for socialization M-F so I can have my full attention on your dog. I currently work from home part time so I have plenty of time for your pet! I am awake early and have a flexible schedule to fit yours. I make sure you and your pet are comfortable with me and follow instruction when caring for your pet. You know your pet best and I want them to be happy and content with me.
How Rover works
1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Walking FAQs
Frequently asked questions about Rover
Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winchester on Rover as of Aug 2025 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, there are 530 dog walkers in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 83% of Winchester dog walkers respond in under an hour.
Dog walkers in Winchester have an average of 15 years of experience. Dog walkers with repeat customers have an average of 2 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winchester.
You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:
- Start and stop times
- A map of their walk with total distance
- Pee, poo, food, and water breaks
- Cute photos and a personalized note
There are 530 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.
Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.
