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: Ryan R.
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Ryan R.
Star Sitter
from
$20
per walk
4.9 out of 5 stars
• 66 reviews
19 repeat clients
13 years of experience
Sapulpa, OK, 74066

About: I have taken care of dogs since I was a little kid, and they’ve always been under the most perfect love and care for so long. I also always make sure they are always happy and beyond. Usually I like to spend time with them and have fun with them a lot, such as playing with them. Usually I’m good with dogs, even when approaching them. It’s very important I understand more about the dog though so I can be friendly with it. I have also done a lot of dog-sitting for my friends who have dogs and cats, and usually their dogs and cats would love me and feel comfortable around me. I’ve also watched over my mom’s friend’s dogs a lot throughout my teenaged years, and they would always end up being just fine and happy! I’d play with them and give them the love and affection they deserve. I’m currently a graduated student from high school who is going to Tulsa Community College for musical theatre and acting after the summer ends, while I also do work a part time job at a restaurant. But I’ll definitely be free a lot to spend time with a dog and play with them and watch them, or even walk them! I always enjoy hanging around dogs and even getting the chance to spend time with one and make one happy. Never will it ever become a problem for me to watch over one at any days of the week. And if it does that will be a rare occasion, but it always important I’m given a week or 2 week notice! (Preferably 2 week notice) then I will definitely be more free. I take good care of my 4 cats in my home, by spending time with them, feeding them, playing with them, giving them love and affection, as well. I’ve also taken good care of my 2 dogs throughout most of my life before they passed away recently. I’d always play with them, make sure they stayed well fed, and I always spent a lot of time with them, making sure they’re fine. I would also dog-sit my friends’s dogs and my mom’s friend’s 2 dogs a lot as a teenager growing up, which I still sometimes do to this day. Even when not dog-sitting, at my friends’s house I’d always come off as friendly and nurturing to their cats and/or dogs a lot, and it would always work usually. But as long as the owners of the other cats or dogs tell me how they’re like and how they take to new people approaching them, I’ll be just fine and be fully capable of approaching them well.

Sitter Profile Image: Kaitlyn M.
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Kaitlyn M.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 45 reviews
18 repeat clients
15 years of experience
Bixby, OK, 74008

“Kaitlyn was super quick to reply and did great with our pup on his walk!”

Profile image
Emily M.
Sitter Profile Image: Brittany C.
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Brittany C.
from
$25
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Tulsa, OK, 74107

About: Hi! I’m Britt, and animals have always been a huge part of my life. I’m an animal lover who truly enjoys caring for animals of all kinds, sizes, breeds, and personalities. I treat every pet in my care like they’re part of my own family. I have professional experience working at Woodland West Pet Resort, where I became a Certified Kennel Technician. This experience taught me how to safely care for multiple animals, recognize their individual needs, maintain clean and comfortable environments, and make sure every pet receives plenty of attention and care. I also have experience caring for a variety of animals, including wildlife. Caring for so many different types of animals has given me a great appreciation for how unique every animal can be. Needless to say I’m up for anything! In addition to my kennel experience, I have experience providing drop-in pet sitting and dog walking, as well as caring for pets in their homes. I’m comfortable with feeding, fresh water, walks, playtime, medication routines when needed, and giving pets the companionship and attention they need while their owners are away. I also have hands-on dog bathing and nail-trimming experience and understand the importance of keeping pets clean, comfortable, and well cared for. Whether your pet needs a fun day of play, a walk around the neighborhood, a drop-in visit, or simply some extra love and attention while you’re away, I would love the opportunity to care for them! Your pets’ safety, happiness, and comfort are my top priorities. Pet care fits naturally into my daily life and schedule. I am a mother of three boys, and my youngest is one. I am also a full-time caregiver to my autistic son when he is not in school. Because of this, I am already structured around being home and available when my family needs me. Providing pet care allows me to support other families while still being present for my children and maintaining a schedule that works around school hours and my caregiving responsibilities. It’s a meaningful way for me to do something I love while balancing my family’s needs. Whether your pet needs a fun day of play, a walk around the neighborhood, a drop-in visit, or simply some extra love and attention while you’re away, I would love the opportunity to care for them! Big or small, I can care for them all! I love animals of all species. Canines, felines, reptiles, avian’s, and exotics. I have a big backyard with plenty of room for playtime, exercise, and potty breaks. Whether your pet stays in my home or I care for them in yours, I’ll always make sure they have fresh water, attention, and everything they need to feel comfortable. Every pet is different, so I’m happy to follow their individual routine and personality. We can enjoy open play and cuddle time with naps in between, or give them space if they prefer some quiet time. My goal is to make every pet feel safe, loved, and right at home!

Sitter Profile Image: Francine L.
Verified Enhanced Background Check
Francine L.
Star Sitter
from
$16
per walk
4.9 out of 5 stars
• 12 reviews
5 repeat clients
1 year of experience
Tulsa, OK, 74120

About: Hello! Let me help you and your pet feel safe and secure. I've been a pet lover for years and now have the time to offer care on a larger scale. In the past I have fostered animals, primarily cats and dogs with the SPCA. During that time I worked with small and larger breeds of various personalities. I have the patience to work with dogs that may be anxious or shy, and dogs that are more rambunctious as well. I love learning about animals, and would even like to become a dog trainer. Let's connect! My schedule is flexible and open at this time. I can work mornings, afternoons, or evenings, and I'm always open to discuss what needs you may have. It's essential to build a relationship with the pet. You want the dog to feel secure, ensure that you can change behavior if needed, and pay attention so that they don't find themselves in trouble.

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The median cost per walk for dog walking in Winchester is $20

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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

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for dog walking - Winchester

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winchester average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester

Frequently asked questions about Rover

As of November 2026, there are 579 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 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 a map of the walking route, 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 Winchester 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 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:

  • 88% of walkers can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% 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 Meet & Greet.

walkers on Rover set their own cancellation policy, 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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