Dog Walking Westchester Gardens

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Westchester Gardens, 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: Megan H.
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Megan H.
from
$14
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
High Crossing, Madison, WI, 53718

About: What sets me apart is my genuine love for animals. Spending time with pets is truly one of my favorite things, and I treat every pet as if they were my own. I enjoy getting to know each animal’s unique personality, whether that means playing with an energetic dog, giving extra attention to a cuddly cat, or providing gentle companionship to a senior pet. I believe pets thrive when they feel loved, comfortable, and understood, so I focus on building trust and creating a positive experience for them while you're away. Being around animals brings me so much joy, and I take pride in making sure they feel happy, safe, and cared for. You can count on me to provide plenty of affection, attention, and personalized care, along with regular updates so you can have peace of mind knowing your pet is in loving hands. I am currently a nursing student at UW Madison and have time throughout both the week and weekend to spend time with your pet! Typically earlier or later in the day is best for me but I am able to be flexible. I care for pets by sticking closely to their normal routine so they feel comfortable and at ease — feeding them on schedule, going on walks, playtime, and any specific instructions from their owner. I spend a lot of time giving attention and affection, whether that’s active play for energetic pets or calm companionship for seniors or more relaxed animals. I always try to make them feel safe and cared for while their owner is away. I also send updates so you know how they’re doing and can feel confident they’re in good hands.

Sitter Profile Image: Ben K.
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Ben K.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
131 reviews
28 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

Our Great Dane loves Ben. He has had great communication with us during all of his walks and has made sure that Bruno has “done his business” in the mornings. He is our favorite walker

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Stephanie C.
Sitter Profile Image: Taryn E.
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Taryn E.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
30 reviews
15 repeat clients
4 years of experience
Windsor, WI, 53598

About: I have had pet care experience with a neighbor for four years now. And I have also helped own a dog for 8 years. With my neighbor I do pet sitting/drop in visits, dog walking, and cat care. With my own dog, I have had him since he was a puppy, and he is my best friend. I have had experience living with him, walking him, feeding him, and bathing and grooming him as well. I would do anything for my dog, and I will transfer that love to all animals I meet. I am a college student and my plan is to do this during my winter break between semesters. Since I will not have school during this time, my schedule is very free and flexible. I am doing this to have something to look forward to every day during break. So I am very open on a daily basis to accommodate to your schedule. My plan is to do services that are in my clients home because my dog right now doesn't always work well with others. So when I am in my clients home I will treat all people, items, and pets with the utmost respect and kindness. I will care for your pets on drop-in visits and on walks like they are my own.

Sitter Profile Image: Emma R.
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Emma R.
Star Sitter
from
$24
per walk
4.9 out of 5 stars
102 reviews
36 repeat clients
35 years of experience
Madison, WI, 53703

Satisfied customer happy, tired pups

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Stephanie J B.
Sitter Profile Image: Mary W.
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Mary W.
from
$17
per walk
5.0 out of 5 stars
10 reviews
5 repeat clients
20 years of experience
High Crossing, Madison, WI, 53718

Mary was amazing to work with. She was very gracious about our last minute need, and wonderful with our dog Toliver. He really enjoyed their walks, and I felt like he was in great hands. I would book with Mary again in a heartbeat.

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Michael S.
Sitter Profile Image: Blaze D.
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Blaze D.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Madison, WI, 53704

About: I’m all of my friends and families first choice to watch their pets when they are out of town. I’ve looked after a variety of breeds of dogs and many cats as well. I’ve always had dogs in my life growing up so I’m very familiar with reading their body language and knowing how to care for them. I work full time but have a lot of flexibility to check on your pet throughout the day and have the opportunity to work remote as well I’ve never a met a pet that didn’t like me. I’m very good at reading dogs body langue and knowing what they need. Cats also like me and I’m good at reading their body language as well

Sitter Profile Image: Carley T.
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Carley T.
from
$18
per walk
5.0 out of 5 stars
10 reviews
5 repeat clients
20 years of experience
Westchester Gardens, Madison, WI, 53704

Tucker would literally try to jump out the kitchen window to get to her for his walk. He loved it so much. Carley was so nice and sweet with Tucker. If we weren't moving across the country I would still want her to walk him

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Rebekah & Alex N.
Sitter Profile Image: Jacob S.
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Jacob S.
from
$12
per walk
5.0 out of 5 stars
8 reviews
3 repeat clients
11 years of experience
Capitol, Madison, WI, 53703

Jacob is amazing and a fast walker! He uses the whole booked time to walk your dog and takes the best pictures too! Support him in his senior year here. You and your dog won’t regret it!

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james a.
Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
68 reviews
18 repeat clients
20 years of experience
Madison, WI, 53718

Jackie is consistent and punctual she treats our lalu as her own takes good care of him and gives him a good walk. Lalu really looks forward to her walking him

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Leo B.
Sitter Profile Image: Keezieng V.
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Keezieng V.
from
$19
per walk
5.0 out of 5 stars
68 reviews
30 repeat clients
3 years of experience
Carpenter-Ridgeway, Madison, WI, 53704

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.

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Colin S.
Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
44 reviews
10 repeat clients
10 years of experience
Madison, WI, 53704

Hailey is so great to work with and I’d hire her again anytime! She is extremely responsive and always gives great pupdates. Plus our pups seem to love her!

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Claire H.
Sitter Profile Image: Sammi S.
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Sammi S.
from
$25
per walk
5.0 out of 5 stars
42 reviews
3 repeat clients
20 years of experience
Madison, WI, 53703

My dog has so much fun with Sammi! Thank you!

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Julie P.
Sitter Profile Image: TAYLOR P.
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TAYLOR P.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
43 reviews
16 repeat clients
15 years of experience
Madison, WI, 53704

Taylor was very kind with Kora and let her take out her frisbee, which she loves to play with in the afternoons.

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María Paula R.
Sitter Profile Image: Sarah W.
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Sarah W.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
59 reviews
19 repeat clients
26 years of experience
Madison, WI, 53704

Sarah took our 13 yo rescue dog for a walk which she really enjoyed. Sarah has taken care of our dog in the past for over night and has always been trustworthy.

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Kathleen M.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
51 reviews
20 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Elizabeth was great with our dog Cash giving us updates with pictures and giving him nice long walks. Will definitely be using her again and highly recommend her.

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Amy L.
Sitter Profile Image: Morgan B.
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Morgan B.
from
$30
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Bluff Acres, Madison, WI, 53704

About: I have been in the vet med field for about 7 years. During this time I have acquired many skills from that would set me apart from many other sitters. Hello everyone! I live a few minutes from Sun Prairie, although, I do work on the west side off of University Ave. I am typically available early morning or after working hours or on lunch breaks. I am also super flexible! We have 3 cats! I usually keep my pets in our finished basement during boarding stays. I am available for walks, potty breaks, meals/medications, and nail trims, at your request.

Sitter Profile Image: Annabella P.
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Annabella P.
from
$17
per walk
5 years of experience
High Crossing, Madison, WI, 53718

About: With over two years of dedicated experience in professional dog and cat boarding and daycare, I offer reliable, knowledgeable, and compassionate care for your pets. My current role as a veterinary assistant provides me with hands-on medical awareness, safety protocols, and a deep understanding of animal behavior, ensuring your pets are in skilled hands whether they need routine care, special attention, or medication administration. Why Choose My Services: Veterinary Experience: Active background as a vet assistant ensures attentive health monitoring, safe handling, and quick recognition of any stress or medical needs. Proven Track Record: Two years of hands-on experience managing daily care, feeding, exercise, and social schedules for both cats and dogs of various breeds and temperaments. Personalized Care: Customized routines for every pet—from energetic play sessions and walks to quiet, comfortable downtime for senior or anxious animals. Hands-On Experience & Animal Knowledge: Growing up and living around my family's 5-year-old dog has given me a lifelong foundation in canine care and behavior. This personal experience, combined with my professional background, helps me understand the unique personalities, routines, and comfort needs of every dog I care for. Whether your dog needs walks or drop-in visits, your pet will receive attentive, professional, and loving care tailored to their unique routine. I will be available for dog walking and drop in visits Monday, Wednesday, Saturday and Sunday. I will be not available outside of this time unless stated. As a working veterinary assistant, keeping your pet safe, happy, and comfortable is my highest priority. I leverage my clinical training and background in animal care to provide a secure environment tailored to your pet's specific needs. I actively monitor for subtle signs of stress or health issues, utilize low-stress handling techniques, and maintain easy access to local emergency veterinary care. I am fully trained to administer oral and injectable medications correctly and safely. My living space is completely pet-proofed—cleaning supplies, toxic items, and small objects are safely secured. Dogs are kept securely on-leash during all neighborhood walks, avoiding high-risk environments like off-leash dog parks to ensure controlled, stress-free outings.

Sitter Profile Image: Marcela M.
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Marcela M.
from
$23
per walk
5.0 out of 5 stars
1 review
4 years of experience
Eken Park, Madison, WI, 53704

About: Hi! My name is Marcela, and I’m a lifelong animal lover with a special place in my heart for both dogs and cats. I have two dogs of my own, Chester and Athena. Chester is my small rescue dog, and I’ve had him since I was 9 years old. I truly grew up with him, and he has been by my side for most of my life. Chester is deaf, and as he’s gotten older, he has also developed anxiety and takes medication to help manage it. Over the years, I’ve learned how important patience, consistency, and understanding an animal’s individual needs can be. I communicate with Chester using hand signals and gentle body language, and caring for him has taught me so much about connecting with animals at every stage of life. Athena is my pit bull, and we love spending time outdoors with our animals. Whether we’re going for walks, playing, or simply enjoying the fresh air, I genuinely love giving animals attention, exercise, and plenty of affection. Athena has also had difficulty getting along with other dogs, so we worked with her through training to help her become more comfortable and learn how to interact appropriately. This has given me firsthand experience with the patience, structure, and careful management that some dogs need when around other animals. I also have hands on experience caring for a cat with significant medical needs. My cat, Fergi, was diagnosed with HCM and eventually developed end stage heart failure. During his illness, I became very familiar with the day to day care that comes with heart failure, including administering medications, monitoring his breathing, appetite, energy, and behavior, and paying close attention to small changes in his condition. Going through that experience also taught me how difficult it can be to leave your pet in someone else’s care when they’re sick or have special needs. I know how much worry can come with wondering if they’re okay while you’re away. Because of that, I want to be the kind of person who gives another pet parent that same sense of comfort and reassurance, knowing their pet is being watched over with patience, love, and genuine care. I absolutely love cats, and after recently losing Fergi, I’m not quite ready to bring another cat into my home yet. I would, however, love the opportunity to care for and spend time with other people’s cats. It would be really special to have that connection again while giving your cat the love and attention they deserve. I also take pride in the everyday care I give my own pets, including brushing my dogs’ teeth daily. I’m happy to provide routine care like this when requested, along with walks, playtime, feeding, medication, and plenty of companionship. Whether your pet is young, a senior, anxious, shy, energetic, or needs medication or extra patience, I’ll treat them with the same kindness and attentiveness I give my own. I know how much trust it takes to leave your pets with someone, and my goal is for both you and your pet to feel safe, comfortable, and cared for while you’re apart. I can’t wait to meet you and your pets! ❤️ I have a flexible schedule since my partner and I run our own microgreens farm. This allows me to work pet care into my schedule and be flexible with walks, drop ins, and stays. I’ll care for your pet(s) based on their individual needs and any instructions you provide—every situation is different, and I’m happy to adapt to what’s best for them.

Sitter Profile Image: Lacey S.
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Lacey S.
from
$20
per walk
5.0 out of 5 stars
16 reviews
2 repeat clients
16 years of experience
Marquette, Madison, WI, 53704

Booked Lacey for my mom and this is her review: I didn’t know what to expect with Roger and Lacey, but my husband was gone and I needed help. The moment she saw Buddy, she immediately made a great connection

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Michelle M.
Sitter Profile Image: Cassandra B.
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Cassandra B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
39 reviews
12 repeat clients
15 years of experience
Madison, WI, 53704

About: I have done petsitting (cats and dogs) for over 15 years. Usually for animals where I personally know the owners and have spent time with the animal to create a bond/relationship. I want to full disclose with new perspective pets parents: I have a full time, in-office job with the standard business hours, Monday through Friday. If that's not what you are looking for in a house sitter, I understand. If I had a pet of my own, I would ensure all their needs are met. As a petsitter, I would to ensure their animal's life doesn't change or I could make it better in some small way especially since their parent(s) is gone I stay at the animal's home to care for them so their life isn't different than what it usually is for them. Changing their environment can be quite shocking and stressful to them. I try not change their lifestyle too much while the parent is gone

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

Dog parents share their Rover experiences - Westchester Gardens

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5.0 out of 5 stars

Amazing as always! I know our pups are in the best hands and that if anything comes up we will know right away!!

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Mary H.
Dog Walking
5.0 out of 5 stars

Megan is amazing!! She is so good with my dog and always makes me feel reassured that she is cared for while I’m gone. Very easy to work with and will be booking again!

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Kaitlin J.
Dog Walking
5.0 out of 5 stars

Francesca is a natural. They were terrific with my pooches. I would recommend them to my friends for sure!

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Liz C.
Dog Walking
5.0 out of 5 stars

OMG I can’t say enough good things about Hannah. Such a wonderful person that truly loves dogs. She was easy to book with, got back to me quickly when I needed to change times, and overall she was just a joy to get to know. My dogs fell in love with her. We will most definitely be rebooking in the future. Top notch!🐶❤️🐶

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Liz C.
Dog Walking
5.0 out of 5 stars

Mary was amazing to work with. She was very gracious about our last minute need, and wonderful with our dog Toliver. He really enjoyed their walks, and I felt like he was in great hands. I would book with Mary again in a heartbeat.

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Michael S.
Dog Walking
5.0 out of 5 stars

Ollie has watched my dog on multiple occasions now and has always provided great service. Always reliable and kind.

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Morgan S.
Dog Walking
5.0 out of 5 stars

Very reliable, my dog absolutely loved her, and I felt safe when she was taking her for a walk. Highly recommended.

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David P.
Dog Walking
5.0 out of 5 stars

Samantha was a godsend for us -- she was a reliable, friendly, and caring dog walker who our gregarious pup, Watson, basically instantly fell in love with. We would still have her walk Watson if she weren't moving! She is fantastic.

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Michelle S.
Dog Walking
5.0 out of 5 stars

Christina was very warm and friendly with Rusty when they first met and came very promptly for their first walk. we look forward to another walk with her.

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Leif B.
Dog Walking
5.0 out of 5 stars

Tucker would literally try to jump out the kitchen window to get to her for his walk. He loved it so much. Carley was so nice and sweet with Tucker. If we weren't moving across the country I would still want her to walk him

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Rebekah & Alex N.
Dog Walking
5.0 out of 5 stars

Keely has been walking my dog Lola every Wednesday for the past couple of weeks, and I truly could not be happier with the care she's provided. I booked with very little notice, reaching out on a Monday, and Keely came over the very next day to meet Lola, learn our routine, and get to know her needs. From the start, I could tell she was thoughtful, thorough, and genuinely invested in making sure Lola felt comfortable and safe. Lola is a reactive dog, and having someone who understands reactive dogs is incredibly important to me. Keely clearly has that experience and confidence. She pays attention to every detail, thinks ahead, and has approached each walk with care and awareness. I feel completely at ease knowing Lola is in her hands. What has impressed me even more is how thoughtful Keely is about factors beyond just the walk itself. We've had plenty of rainy weather lately, and she's done an amazing job timing walks to avoid the worst of it. She's also been mindful of potential thunderstorms and how Lola might react, which shows just how much she cares about the dogs she works with. Keely has been an absolute pleasure to work with - reliable, communicative, knowledgeable, and genuinely caring. I'm so grateful to have found her, and I know Lola is too. I would recommend her without hesitation to anyone looking for someone they can trust completely with their dog.

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Crystal F.
Dog Walking
5.0 out of 5 stars

Anna always shows up, rain or shine! She's reliable,communicative, and super sweet. My dog and cat both absolutely adore her

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Melissa T.
Dog Walking
5.0 out of 5 stars

Elizabeth was great for Lacey today. She was prompt with messaging and very flexible to walk her the next day.

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Allison H.
Dog Walking
5.0 out of 5 stars

Brittany has been great as our dog’s regular walker. Punctual, so reliable, and I can tell from the pictures my dog has a great time with her! Can’t recommend her highly enough.

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Serenity V.
Dog Walking
5.0 out of 5 stars

Alexandria is amazing with my dog and provides great updates each day after their daily walk. She’s reliable, shows up on time, and spends the full time. I feel so lucky to have found her!

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Kelsey T.
Dog Walking
5.0 out of 5 stars

Megan is outstanding and very responsive and flexible. She is super kind with any animals and that helps with any cat or dog that needs her services.

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Scott S.
Dog Walking
5.0 out of 5 stars

Lydia did a great job taking my energetic golden retriever for a walk and sending me lovely photos :)

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Kat F.
Dog Walking
5.0 out of 5 stars

Lora was reliable and really gave extra. She came out before hand to learn the dogs and their routes. I am currently disabled and she was so helpful bringing in packages. She took each dog on extra laps if they failed to do their business the first round. We will not hesitate to call Lora the next time we need someone.

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Cheri H.
Dog Walking
5.0 out of 5 stars

Lindsay is amazing!! She was able to come over and take my golden retriever for a walk and to the dog park. She also has a dog who was able to join in on the fun, which is always great for my dog who loves to play! She’s super kind and easy to work with. I definitely recommend her, and will be booking her again in the future!

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Kelli G.
Dog Walking
5.0 out of 5 stars

Sylvia was great with our little shy doggie. She was patient & caring- taking the time to let or dog get used to her before they walked. No wonder she is a star sitter.

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Hex H.
Dog Walking
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