Dog Walking Woodlands

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Woodlands, 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: Ryan H.
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Ryan H.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
22 reviews
4 repeat clients
15 years of experience
Stonefield Woods-Ridge, Madison, WI, 53717

About: I work from home and have flexible hours. My dog loves to play with other dogs and would love to have a friend on walks or to play in our fenced-in yard! Also available to go on solo walks if needed. Can also have behaved dogs stay over during day or night; they will get plenty of love from our dog and our two daughters. Can take the dog for walks, to dog parks, or just hang out in our back yard. I work from home. I can take dogs for walks or dog parks most times during the week, as my meetings can be handled from my phone. If dogs are friendly with our dog, the dog can come play at our house in our fenced in back yard. Weekend mornings are usually free for walks, and depending on kid activities can fit in walks and feedings during the afternoon/evening. I have a fenced in yard and a dog (Australian Shepard) that gets along with almost every dog he’s met. Have many dog toys for play. Neighborhood for walks is quiet and has many friendly dogs. At client’s home, will provide feedings, walks, and/or in-home playtime.

Sitter Profile Image: Christian O.
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Christian O.
from
$12
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Summit Woods, Madison, WI, 53711

Christian was very responsive and great with our dog. Easy to coordinate with and sent helpful updates. Will definitely use again!

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Danae A.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
80 reviews
27 repeat clients
14 years of experience
Middleton, WI, 53562

Stephanie is great, and I'm going to have to come up with reasons to book her again, because my pups are going to miss her. Punctual, good communication, and comfortable with ACDs, which is not always easy. Highly recommend.

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Rod G.
Sitter Profile Image: Chelssey H.
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Chelssey H.
from
$12
per walk
5.0 out of 5 stars
3 reviews
16 years of experience
Madison, WI, 53705

About: Dogs are a huge part of my life! Before moving to Wisconsin, I owned and operated a dog walking and overnight boarding business in Maryland for two years. These days, I spend much of my time fostering dogs for a local rescue, helping them decompress, learn home life, and get ready for their forever families. With three personal dogs, I’m very comfortable managing a multi-dog household and all the different personalities that come with it. I’ve cared for everything from energetic, playful pups to seniors who prefer a cozy spot on the couch, as well as rescue dogs who need extra patience, structure, or time to feel comfortable. Fostering has taught me that there really isn’t a “one size fits all” approach to dogs. I pay close attention to body language, respect boundaries, make thoughtful introductions, and adjust my approach based on what each individual dog needs. I also know how hard it can be to leave your dog behind and wonder how they’re doing. You can expect daily updates from me, including plenty of photos and videos, so you can see how your dog is settling in and what they’ve been up to. My goal is to give your dog a safe, comfortable, fun place to stay—and give you the peace of mind that they’re with someone experienced, attentive, and who truly gets dogs. Pet care fits very naturally into my everyday life. I’m a stay-at-home mom to a middle schooler and work remotely part-time, which means I’m home quite a bit and have plenty of flexibility to give the animals in my care lots of attention, love, potty breaks, walks, playtime, and downtime. With three resident dogs—a 70 lb senior mix, a 2-year-old Boston Terrier, and a 1-year-old English Bulldog/French Bulldog mix—and all three started out as fosters who never left! I continue to foster regularly and work very closely with a local dog rescue, so welcoming another dog into our routine is something the dogs are very accustomed to. Dogs staying with us aren't spending the day alone waiting for someone to come home from work. I'm around throughout the day to keep an eye on everyone, accommodate individual routines, and provide plenty of attention (or a cozy place to nap, if that's more their speed!). Pet care is genuinely part of my everyday life, and I love it that way. Here, pets are treated like part of the family. My dogs are kennel trained, but they're also welcome throughout the home—including on the furniture and beds. I'm happy to follow your lead, though! If your dog sleeps in a crate, follows certain house rules, eats on a specific schedule, or isn't allowed on furniture at home, I'll do my best to keep their routine consistent. I live in a large apartment, so all outdoor time is supervised and on leash. I'm very comfortable with puppies and their extra needs, including frequent potty breaks, potty pads, crate training, and the general chaos that comes with puppyhood! I have extra crates that can accommodate dogs up to approximately 75–80 lbs, plus more dog beds and toys than any household probably needs. If your pet has food or environmental allergies, please let me know. I am very accustomed to managing allergies and am happy to follow specific instructions regarding food, treats, medications, or environmental triggers. Because your dog will share our home with my husband, middle-school-aged child, and our three resident dogs, dogs staying with us must be comfortable with older children, men, and other dogs. I take introductions and dog body language seriously and want every animal in the house—yours and mine—to feel safe and comfortable. While others do live in the home, I will be the caregiver for any other animals. For care in your home, I'll follow your lead. You know your pets and their routine best, and my goal is to keep things as familiar and consistent as possible while you're away. I'm also happy to care for more than just dogs during in-home visits—cats and other household pets are welcome, too! Whether your pet stays with us or I care for them in their own home, I'll treat their individual routine as exactly that: individual. Some pets want to be your shadow, some want nonstop playtime, and some would prefer that I serve dinner promptly and otherwise respect their personal space. I'm good with all three!

Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
139 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

Michelle is spectacular! This was my first Rover experience and I was quite concerned my pup wasn't going to cooperate with a (relative) stranger for a walk BUT from the moment they met for a Meet and Greet Michelle was his friend. It's obvious she truly loves dogs and I know mine loves the time they spend together. I strongly recommend Michelle to any Rover user and will recommend this app to friends.

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Dan D.
Sitter Profile Image: Ashley E.
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Ashley E.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
613 reviews
147 repeat clients
13 years of experience
Madison, WI, 53705

Ashley does a great job with my anxious 70lb pittie and really pushes him to walk far (which is something we normally do). She’s punctual and reliable. I’m so lucky to have found her!!

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Heather K.
Sitter Profile Image: Hillary L.
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Hillary L.
from
$22
per walk
5.0 out of 5 stars
168 reviews
52 repeat clients
12 years of experience
Vilas, Madison, WI, 53711

Hillary did an amazing job walking my shy pup and quickly won her over! In addition to being amazing with my dog, Hillary did and excellent job communicating with me about how my dog did on their walks, tactics she used to help build up my dog's confidence, and Hillary even helped clean up a potted plant that my dog had knocked over one day. I would highly recommend Hillary to anyone looking for care for their pets!

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Hannah L.
Sitter Profile Image: Becky & Judd W.
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Becky & Judd W.
from
$17
per walk
5.0 out of 5 stars
33 reviews
4 repeat clients
3 years of experience
Madison, WI, 53719

Truman was very awesome!! He did great with our boy, Zissou!

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Taylor B.
Sitter Profile Image: Alliyah D.
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Alliyah D.
from
$18
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
2 years of experience
Wexford, Madison, WI, 53717

Aliyah responded very quickly to my request for dog walking while I couldn't get my 2 large fur babies out. She was kind, quick to bond with them, lovely to chat with and although it was a splurge for me it definitely feels worth it. The dogs liked her immediately, which isn't always the case with our oldest, more shy Sheepadoodle. As I write this, they are spread out on the floor tired, so goal met. I'll definitely ask for Aliyah's help again.

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Jennifer C.
Sitter Profile Image: Jesse T.
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Jesse T.
from
$15
per walk
5.0 out of 5 stars
28 reviews
12 repeat clients
1 year of experience
Madison, WI, 53719

Jesse is reliable, communicative and an excellent pet photographer.

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Sarah N.
Sitter Profile Image: Bethany W.
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Bethany W.
from
$16
per walk
5.0 out of 5 stars
3 reviews
2 years of experience
Madison, WI, 53705

About: I am a vet student who has experience taking care of other dogs, cats, and even birds while working in a vet clinic! I am able to administer medications, take care of senior pets, and those with disabilities!! Growing up, I also have taken care of both cats and dogs in my family😊. I am currently only working virtually and part-time for a research paper in veterinary medicine, so I am able to comfortably accommodate Rover and pet-sitting in my schedule! I have learned in the past to adhere to owners’ specific instructions and ask questions if they arise to provide the best care for their pet. While taking care of pets in the vet clinic, I respect their boundaries, closely monitor their health/behavior, and try to minimize any stress or fear they could be experiencing. With pets at home, I love to spend as much time giving them love and affection or stimulating their mind with play-time and toys!

Sitter Profile Image: Austin C.
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Austin C.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
88 reviews
31 repeat clients
5 years of experience
Madison, WI, 53719

Austin is reliable, flexible, and overall great to work with. He does a great job with my large reactive dog, and I definitely will continue to book with him in the future. Thanks Austin!

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Isaac W.
Sitter Profile Image: Megan B.
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Megan B.
from
$20
per walk
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

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

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Andy O.
Sitter Profile Image: Stina S.
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Stina S.
from
$22
per walk
5.0 out of 5 stars
9 reviews
4 repeat clients
9 years of experience
Middleton, WI, 53562

Stina is a very good communicator, she has a very pleasant personality, and she gave my pup a nice long walk.

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Judy C.
Sitter Profile Image: Madalyn M.
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Madalyn M.
from
$30
per walk
5.0 out of 5 stars
4 reviews
5 years of experience
Middleton, WI, 53562

About: I enjoy caring for energetic dogs and love keeping them active through games like fetch and tug-of-war. I am a dependable and attentive pet sitter who is comfortable administering medications and providing any additional care your pet may need. I strive to build trust with every pet I care for, and I’m proud that many of my clients have chosen me as their recurring pet sitter. My goal is to ensure every pet feels safe, comfortable, and well cared for while their owners are away. I am currently available through the beginning of August and am happy to discuss scheduling to find a time that works for you. Please feel free to message me with any questions about my availability. I typically provide care in your home to help keep your pets comfortable in their familiar environment. I can also welcome your furry family members into my home for stays of up to two days, if needed. While I do not have a fenced yard, I make sure every dog gets plenty of exercise through long walks and trips to local parks. If your dog enjoys socializing with other dogs and you approve, I’d be happy to take them to a dog park for additional play and enrichment. Your pet’s safety is always my top priority. I carefully follow your care instructions and make sure every dog in my care receives plenty of love, attention, exercise, and responsible supervision. My goal is for every pet to feel safe, happy, and well cared for while you’re away.

Sitter Profile Image: Austin M.
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Austin M.
from
$30
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
29 years of experience
Park Ridge, Madison, WI, 53719

About: Caring for dogs isn't just something I do. It's something I'm genuinely passionate about. I have experience caring for dogs of all ages, personalities, and energy levels, from young puppies learning routines to senior dogs who need a little extra patience and attention. I understand that every dog is different, and I take the time to get to know each pet's unique needs. I'm comfortable with feeding schedules, administering oral medications, crate training, basic puppy training, leash walking, playtime, and providing plenty of love and attention. I'm also attentive to changes in behavior or health and believe it's important to catch anything unusual early and communicate it with owners right away. I know how stressful it can be to leave your pet with someone else, so I make it my priority to provide a safe, clean, and calm environment where they feel comfortable. Whether your dog loves long walks, playing fetch, or simply relaxing with company, I'll make sure they receive the care and attention they deserve. Communication is very important to me. I'll provide regular updates, photos, and messages so you can enjoy your time away knowing your pet is in good hands. My goal is to care for every pet as if they were my own and give owners complete peace of mind. Pet care is already a major part of my daily routine. My day is structured around caring for dogs, so adding walks, drop-in visits, daycare, or boarding fits naturally into my schedule. Because I'm already following consistent routines for feeding, exercise, potty breaks, playtime, and cleaning, I'm able to provide dependable, attentive care throughout the day. I have a flexible schedule that allows me to give pets the time and attention they deserve rather than leaving them alone for long periods. Whether your pet needs a consistent routine, extra exercise, medication, or simply companionship, I'm committed to making sure they feel safe, comfortable, and well cared for while you're away. Safety and comfort are my top priorities when caring for pets, whether in my home or a client’s home. I make sure every pet is in a clean, secure, and calm environment where they can feel relaxed and stress-free. I follow each pet’s routine closely, including feeding schedules, potty breaks, exercise, and any special instructions provided by the owner. I pay close attention to behavior and overall well-being so I can quickly notice if something seems off and communicate right away. In my care, pets are never left unattended for long periods. I supervise interactions, provide structured playtime, and ensure a safe environment at all times—especially when introducing pets to new surroundings or other animals. I also respect the client’s home fully when providing in-home care, keeping everything clean, secure, and exactly as I found it. I understand how important trust is when someone allows you to care for their pet or enter their home, and I take that responsibility seriously. My goal is to make sure pets feel safe, loved, and comfortable, while giving owners complete peace of mind through clear communication and reliable care.

Sitter Profile Image: Amber K.
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Amber K.
from
$20
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Wisconsin Co-Op Housing, MADISON, WI, 53705

About: We have 3 cats and a mini Dachshund, all rescues. Reliable, respectful, dependable. All-around animal-person, committed to keeping animals safe and happy - I strongly believe that people have a responsibility, duty to care for and love all animals; it’s a privilege to have a relationship with them, and we should foster and nurture that. Interested in teaching basic dog commands. Will learn to administer shots if needed. Sensitive to changes in behavior that could signal unhappiness, illness. In the future, hope to create a doggy sanctuary, so I can have many dogs of my own to love and care for every day. I just love dogs & cats & all animals! Value open and clear communication with owners to better care for their pets and to build healthy relationships between us all. My availability has some flexibility, so contact me to discuss! Recently retired and looking forward to devoting time and energy doing things I love, including caring for and building bonds with furry friends. Prefer scheduling ahead of time but will do my best to accommodate same-day requests. All care will be provided according to your instructions. For daycare service provided at my home, I would take dogs out on leash at regular intervals because my yard is un-fenced. Kitties and doggies are loved and treated with kindness and respect.

Sitter Profile Image: Nicole P.
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Nicole P.
from
$20
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
5 years of experience
Sauk Creek, Madison, WI, 53717

About: I have a dog of my own and I’ve done boarding, drop ins and walks before. I’ve grown up with dogs in the house and have watched family friends dogs numerous amounts of times. I currently work full time (8-4:30) during the week, but can do evenings on week days and any time during weekends! I am very flexible and can make anything work! I can abide by whatever schedules/routines you have in place. If your dog likes to socialize, my dog would be a great buddy! I understand dogs need to follow certain rules and need to be let out/fed in a timely manner.

Sitter Profile Image: Michelle G.
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Michelle G.
from
$25
per walk
5.0 out of 5 stars
12 reviews
7 repeat clients
5 years of experience
Spring Harbor, madison, WI, 53705

Michelle is great!! My dog is very shy and slow to warm up to people so I was worried about finding someone to walk him while we are at work but Michelle has been awesome!

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Marissa G.
Sitter Profile Image: Anaya S.
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Anaya S.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
45 reviews
15 repeat clients
10 years of experience
Fitchburg, WI, 53719

Anaya was wonderful with our two dogs. She was always on time and provided timely responses to questions and updates on our fur babies. We would love to have her take care of our dogs again!

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Matt H.
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The median cost per walk for dog walking in Woodlands is $20

Dog parents share their Rover experiences - Woodlands

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5.0 out of 5 stars

Chelssey did such a great job walking Charlie! She made sure he had fresh water before she left and was so thoughtful about all of the little things I have set up to help Charlie behave while I’m away, like keeping the bins in front of the door so he doesn’t scratch. I really appreciated how attentive and caring she was. Your pup is definitely in good hands with Chelssey!

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Kristen A.
Dog Walking
5.0 out of 5 stars

Rebecca was great with Milo, on time, and provided detailed update on the walk. Will definitely want to hire her again.

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Greg B.
Dog Walking
5.0 out of 5 stars

Quinn was punctual, kind, and clearly experienced with animals. I came home to a happy and tired dog at the end of every day. Highly recommend!

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Jack T.
Dog Walking
5.0 out of 5 stars

Christian was very responsive and great with our dog. Easy to coordinate with and sent helpful updates. Will definitely use again!

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Danae A.
Dog Walking
5.0 out of 5 stars

Robert did a great job walking our dog. He was punctual and very responsible. He is becoming our "go to" dog sitter and walker!

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Cheri F.
Dog Walking
5.0 out of 5 stars

Abby was great looking after Moose while we were out of town for a couple days. Super responsive / communicative and flexible for a late notice booking. Would definitely book with Abby again!

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Ashley G.
Dog Walking
5.0 out of 5 stars

Jennifer is great with my big goofy boy….she adapts to weather conditions and my dog’s needs with care and attention for his comprehensive wellness. He loves his walks…more like sniff adventures…just as much as he loves the house hangouts where he can have a great mix of play and couch hippo experiences. Definitely a 5 tail wag review from us!

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Elaina M.
Dog Walking
5.0 out of 5 stars

Austin is reliable, flexible, and overall great to work with. He does a great job with my large reactive dog, and I definitely will continue to book with him in the future. Thanks Austin!

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Isaac W.
Dog Walking
5.0 out of 5 stars

Anna is amazing with my animals and they adore when she visits and takes care of them. They are always happy and happily tired when I get home!

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Wendy B.
Dog Walking
5.0 out of 5 stars

Meeting Natalie was a pleasure. Warm charming personality. Followed through on questions promptly, on time. Highly recommend Natalie. In future will request her again.

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Dennis R.
Dog Walking
5.0 out of 5 stars

Clara was great to work with! Attentive, flexible, and accommodating - even as I gave her the wrong garage code. My pup was tired after the walk, obviosuly happy, and the pictures were an added bonus. I'd trust Clara with my gal any day!

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Emily J.
Dog Walking
5.0 out of 5 stars

Michelle is very courteous and my dog loved being walked by her. Michelle was respectful of my home, and I would highly recommend her to everyone.

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Sara W.
Dog Walking
5.0 out of 5 stars

Nyx is very shy and timid. Isabel was so patient and kind with her and was able to get her out for multiple walks!

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Natalee P.
Dog Walking
5.0 out of 5 stars

Aliyah responded very quickly to my request for dog walking while I couldn't get my 2 large fur babies out. She was kind, quick to bond with them, lovely to chat with and although it was a splurge for me it definitely feels worth it. The dogs liked her immediately, which isn't always the case with our oldest, more shy Sheepadoodle. As I write this, they are spread out on the floor tired, so goal met. I'll definitely ask for Aliyah's help again.

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Jennifer C.
Dog Walking
5.0 out of 5 stars

Hannah always seems to bail us out when we are in a pinch!!!! She is the absolute sweetest human!! Recommend her 100x over!!

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Kourtney K.
Dog Walking
5.0 out of 5 stars

Allegra has been walking our mastiff and doing a great job working on leash skills. We got Bixby as a rescue so he’s needed a lot of extra TLC to relearn things at 3-4 years old. Allegra totally gets him.

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Emily B.
Dog Walking
5.0 out of 5 stars

Claire was amazing! She was so friendly, and easy to coordinate with, and arrived in a timely manner . You can tell she really loves dogs. Bella was tired after the walk, which was much needed after being home alone today. Would recommend Claire for anyone in the Madison or Sunprarie area with pups in need of a good walk!

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Damanique F.
Dog Walking
5.0 out of 5 stars

Thank you so much for your outstanding care of our girl, Nala! We are always so grateful for your time and care

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Jacquelynn A.
Dog Walking
5.0 out of 5 stars

Here’s a shorter version: --- Melissa is a fantastic dog sitter! She communicates clearly, sends great updates, and is genuinely thoughtful about my dog’s needs. I always feel at ease knowing my dog is with her. Highly recommend!

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Mitchell R.
Dog Walking
5.0 out of 5 stars

Took plenty of pictures, adjusted to my dog’s desired level of activity, and troubleshot a key/cat toy issue. Communicative, friendly, and on-time. Would hire again!

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Carrie P.
Dog Walking
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