Dog Walking in Oakwood Village, Madison, WI
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Oakwood Village dog walkers


“Allegra is the best with my dogs. She is responsible, great at quick communication, and truly treats my pups well when we need her to walk the. Or stay the night. We cant say enough nice things about Allegra.”


“Melinda is a wonderful dog walker. She quickly established rapport with our dog and has been very reliable and responsive. She lets us know how each visit went and often sends photos. I recommend her highly.”


“Keezieng has been a fantastic dog walker this past week! Very flexible and always on time, he made sure that Stella always had a nice mid-day walk.”


“Caring, my dog gets so excited when Mindi walks in, she takes time to play w/ her after the walk and give her lots of love and treats. I know my dog is in good hands w/ Mindi.”


“Great first walk with Pete! Helped him to feel calm and connected with treats before the headed out. Felt great to know Pete was in good hands!”



“Michelle was absolutely fantastic with Kona. Our pup is nervous around new people and Michelle was amazing on her first visit/walk to meet her in advance of her house/pet sitting. After her walk and getting to know Kona, Michelle did a thorough walk through of our house and asked all the little questions and details that I’d never think to talk about before she comes to sit. I’m so confident that she will be an amazing sitter while we are away!”



“Jennifer is great! We'd love for her to walk our dog again (in fact we already rebooked). We needed help once a week with our 8mo puppy. Jennifer always picks him up on schedule and returns him happy and well exercised! Our dog loves everyone but my husband is convinced the pup loves Jennifer extra.”


About: I’ve taken care of dogs, cats, & many other animals since I was young! I currently have two English Cocker Spaniels - they are sweeties! My husband and I got them as pups and trained them ourselves. I feel very confident working with puppies and I adore them. The dogs I grew up with were all rescues, so I also feel confident in caring for rescue dogs that may have more difficult pasts or behaviors. We had a senior chihuahua up until a year ago- she was my everything! Big or small, active or couch potato, I’m happy to care for your special ones. I am happy to get out and walk, run, bike, train or play as well as cuddle up and give some loves. (: I have a flexible work schedule and can easily fit in part-time pet sitting. I’m happy to come by for an hour or two in the afternoon as well as stay the night and keep the animals active morning and evening. I typically try to avoid leaving pets for more than 5 hours- it’s typically 2-4. I have two sweet, easy going boys that are very happy to play and hang out with other dogs in the owner’s home if they would like. I am flexible- I have watched active dogs, low-key dogs, dogs that need extra love and attention, and everything in between. I’m an active person and am happy to take dogs on longer walks or runs, even. My lifestyle is such that doing activities with animals fits in well with the day-to-day.

“Austin was fantastic walking Mazie! Great communication, lots of pictures, and she was tired and seemed very comfortable and happy. I recommend to everyone!”


“Really appreciated Annie walking my sweet dog for me! She’s very trustworthy and great!”



“Ashley is wonderful! She's on time, communicative, and great with my dog. I love using her and will continue to for as long as she'll have me!”


About: I’ve been caring for pets for years, starting with walking dogs for my neighbors — from tiny terriers to big, energetic labs. That hands-on experience taught me how to handle different sizes, breeds, and personalities with confidence and care. What sets me apart is my calm, reliable nature and genuine love for animals. I’m comfortable with leash training, reading dog body language, and keeping even the most energetic pups engaged and happy. I’m also attentive to each pet’s needs — whether that means a brisk walk, a slow stroll for a senior, or extra cuddle time. Your pet’s safety, routine, and happiness always come first with me. I have a very flexible schedule and am available anytime — weekdays, weekends, and even holidays. Pet care fits perfectly into my routine because I truly enjoy spending time with animals and can easily adjust my day around their needs. Whether it's an early morning walk, midday visit, or evening check-in, I’m ready whenever your pet needs me. When caring for pets in a client’s home, I treat it as my own. I follow all routines closely from feeding times to walks and medication and always prioritize your pet’s comfort and safety. I keep a calm, clean environment and make sure pets feel secure, whether they’re outgoing or shy. I pay close attention to details like locked doors, clean water bowls, and tidy spaces. I’m also happy to send regular updates and photos, so you can feel confident and connected while you're away.

“Great job”


“Megan did a great job with Sami while we were away! We would definitely use her again!”


About: I have been pet/house sitting for about a year but have had pets and taken care of animals my whole life. I am open to watching any animals and even doing chores while you’re away! I am available for weekends and afternoons during the school year and all days of the week during summer! I might be out for an hour or two to go to the gym but otherwise can hang with furry buddies all hours of the day. I can be around your pets to watch them at all times if needed. I can crate dogs and make sure they stay where they should be.

“Alisyn has been wonderful with our dog, Indy! We would highly recommend her for dog walking. She is professional, dependable, and communicative. Most importantly, she made Indy feel very comfortable right away. We greatly appreciate the Rover (Report) Cards and photos after every walk. Thank you, Alisyn!”


About: Hi, my name is Ava! I am looking to provide dog walking & check in services in the West Madison area. I am committed to providing individualized care, strong attention to detail, and genuine interest and compassion for animals. I grew up in a family that took in a variety of pets to provide a safe home. I am a strong believer in your fuzzy friends being your best friends! They deserve to be treated with care and love while you're away, just as I would want for my dog. I rescued my miniature pinscher 6 years ago and she is now 15 years old! She is both an old lady and still my little baby. I love all animals and I'm so excited to meet yours! I have experience working with children and youth with diverse needs, and that level of care and patience extends naturally to animals with anxiety, behavioral challenges, or special routines. My background in caregiving and support work has taught me to be highly responsible, communicative, and reliable. I’m organized, dependable, and quick to respond — qualities that give pet owners peace of mind. I also go the extra mile with photo updates, customized activities, and keeping pets happy and stress-free while their humans are away. I’m active and love outdoor time — whether it’s long walks, playing fetch, or trail adventures, I’m happy to match your dog’s energy level. I work from home so I have a flexible schedule from 7am-5pm, but it is not consistent every day. I am able to work my schedule around visits and walks if I have enough time to plan. Just message me with details! I could board pets during the day if it's a small dog with no aggression. I have a 15 year old miniature pinscher that gets anxious around medium-large dogs that have anxiety as well and/or some aggression. I am happy to do drop ins and walks throughout the day!

“Shaina is the best! She takes great care of our two fluffballs - they love her. She’s also incredibly friendly and considerate. Would highly recommend!”


About: I have had dogs my entire life. They ranged from puppies all the way to them becoming senior dogs, and they all came from very different backgrounds. I am especially good with senior dogs. My childhood dog eventually had severe arthritis and needed medication and some extra help. I would do anything for her that helped her feel more comfortable! I also puppysit for some family members so I am also used to the craziness a puppy can bring! I am currently available most days at any time until August 11. My cat does need medication at 8pm, but any other time of the day works for me! I can care for your pets however you need in your home! Whether it's going on a walk, playing outside, or staying inside, whatever is best for them is doable!

“Meeka was amazing! She was very thorough and made sure that Sadie had a good time on her walks! She sent lots of pictures and gave me a detailed summary of her cares. Would definitely recommend ☺️”

Loving dog walkers in your neighborhood
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Allegra R.
Star Sitter


“Allegra is the best with my dogs. She is responsible, great at quick communication, and truly treats my pups well when we need her to walk the. Or stay the night. We cant say enough nice things about Allegra.”


Melinda N.Star Sitter

“Melinda is a wonderful dog walker. She quickly established rapport with our dog and has been very reliable and responsive. She lets us know how each visit went and often sends photos. I recommend her highly.”


Keezieng V.Star Sitter

“Keezieng has been a fantastic dog walker this past week! Very flexible and always on time, he made sure that Stella always had a nice mid-day walk.”


Mindi L.Star Sitter

“Caring, my dog gets so excited when Mindi walks in, she takes time to play w/ her after the walk and give her lots of love and treats. I know my dog is in good hands w/ Mindi.”


Ann V.Star Sitter

“Great first walk with Pete! Helped him to feel calm and connected with treats before the headed out. Felt great to know Pete was in good hands!”




Michelle S.
Star Sitter


“Michelle was absolutely fantastic with Kona. Our pup is nervous around new people and Michelle was amazing on her first visit/walk to meet her in advance of her house/pet sitting. After her walk and getting to know Kona, Michelle did a thorough walk through of our house and asked all the little questions and details that I’d never think to talk about before she comes to sit. I’m so confident that she will be an amazing sitter while we are away!”




Jennifer L.
Star Sitter


“Jennifer is great! We'd love for her to walk our dog again (in fact we already rebooked). We needed help once a week with our 8mo puppy. Jennifer always picks him up on schedule and returns him happy and well exercised! Our dog loves everyone but my husband is convinced the pup loves Jennifer extra.”


Kaelena K.
“We really appreciated Kaelena’s care and attention she gave to our senior dog. We would highly recommend her to watch & care for other people’s pets.”


Austin C.Star Sitter

“Austin was fantastic walking Mazie! Great communication, lots of pictures, and she was tired and seemed very comfortable and happy. I recommend to everyone!”


Annie J.
Star Sitter


“Really appreciated Annie walking my sweet dog for me! She’s very trustworthy and great!”




Ashley E.Star Sitter

“Ashley is wonderful! She's on time, communicative, and great with my dog. I love using her and will continue to for as long as she'll have me!”


Chenghao X.
“Chenghao is a pet-lover through and through. He is incredibly kind, patient, and caring with not only our cat, but he also would offer to help take care of our friends’ and neighbors’ pets just because he enjoys spending time with our furry friends. I would recommend him for anyone who needs a pet sitter!”


Anna N.

“Great job”


Megan B.

“Megan did a great job with Sami while we were away! We would definitely use her again!”


Rex E.
“Rex is an amazing pet caregiver. He took care of my menagerie of two dogs and two cats in my home while I was away. My shy cat who usually hides when someone is on the house he doesn’t know came out and cuddled with Rex the first night. Rex is responsible, reliable, caring, kind and completely trustworthy. I recommend him without reservation.”


Alisyn L.

“Alisyn has been wonderful with our dog, Indy! We would highly recommend her for dog walking. She is professional, dependable, and communicative. Most importantly, she made Indy feel very comfortable right away. We greatly appreciate the Rover (Report) Cards and photos after every walk. Thank you, Alisyn!”


Ava H.
“Ava is a wonderful caregiver for any creature. Working with special needs families and having pets all her life make her more than qualified to handle any loved one. She is highly organized, always kind, and very dependable. You can count on Ava!”


Shaina N.

“Shaina is the best! She takes great care of our two fluffballs - they love her. She’s also incredibly friendly and considerate. Would highly recommend!”


Ella O.
“Ella has lived with pets her entire life. She has actively assisted in the care of her families 3 dogs and 2 cats. Whether it was feeding, playing, walking, or simply cuddling with them, she did it all! Ella loves all animals, is trustworthy and dependable. Ella has a soft spot for senior pets, and she even adopted a senior cat from a shelter. You can trust that your pet will get all the love and attention with Ella as their caretaker!”


Meeka M.Star Sitter

“Meeka was amazing! She was very thorough and made sure that Sadie had a good time on her walks! She sent lots of pictures and gave me a detailed summary of her cares. Would definitely recommend ☺️”
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.
Doggy Walking FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, dog walkers on Rover respond in under an hour.
Experience can vary widely from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when comparing dog walkers available in Oakwood Village.
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
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.
