Dog Walking Middleton

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Over 188
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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
21 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: Stefanie B.
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Stefanie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
77 reviews
26 repeat clients
14 years of experience
Middleton, WI, 53562

Stephanie was great with my sometimes challenging Australian cattle dogs. She communicated well, was flexible in terms of exact timing, and really seem to enjoy my pups, and they really like her. Highly recommended.

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Rod G.
Sitter Profile Image: Chelssey H.
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Chelssey H.
from
$10
per walk
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: Austin M.
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Austin M.
from
$20
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
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: Michelle S.
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Michelle S.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
138 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

Michelle was great with my great with my dog who was being extra difficult. She was very communicative and able to get my dog outside. Can’t thank her enough!

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Cally G.
Sitter Profile Image: Quinn M.
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Quinn M.
from
$12
per walk
8 years of experience
Madison, WI, 53719

About: I have been surrounded by and have taken care of dogs since getting my family’s two dogs when I was around 11 or 12 years old. Even since moving out, my family has relied on me to take care of them on vacations, extended work trips, etc. I now have two cats of my own, and love any opportunity to meet new animals. I am currently traveling the country, and looking to explore new places! I’ve found that pet-sitting is an excellent way to do so, with the side bonus of getting to meet new furry friends along the way! I am very intentional about adapting to each pet’s individual needs - whether they’re a fast friend or needs some space to figure me out first, my top priority is establishing trust with your fur baby. From there, I can ensure that I give them the proper love and care they deserve.

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: Jesse T.
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Jesse T.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
27 reviews
11 repeat clients
1 year of experience
Madison, WI, 53719

About: I have experience working at Paw Pals taking care of cats and dogs. I have also raised and cared for hamsters, horses, birds and bunnys. I'm currently working part-time to only care for animals so I have plenty of time for your animals! Let me know when you need me and I will be there! They will get the time they need. ❤️ Your pet will have the whole downstairs to themselves and lots of play space. I have two friendly cats that are willing to be friends with your pets but they will be upstairs. There are multiple grassy areas to run around in around my condo and trails to walk your pet that will allow them to play in. Treats treats treats❣️

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: Ashley E.
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Ashley E.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
609 reviews
146 repeat clients
13 years of experience
Madison, WI, 53705

Ashley is always so reliable!! When my husband travels and I am at a work all day it’s great knowing my dogs are still getting their exercise! My 18 month old border-jack really needs it!! My 13 year old border Collie just likes a little attention!

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Sue L.
Sitter Profile Image: Hillary L.
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Hillary L.
from
$22
per walk
5.0 out of 5 stars
166 reviews
50 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: Austin C.
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Austin C.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
85 reviews
31 repeat clients
5 years of experience
Madison, WI, 53719

Austin did a great job walking Carmello. He responded to a last minute booking and I couldn’t have been more happy with his services. Have already booked him again and hopefully more in the future.

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Melissa 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: Anaya S.
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Anaya S.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
44 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.
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: Jamie K.
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Jamie K.
from
$20
per walk
5.0 out of 5 stars
53 reviews
16 repeat clients
14 years of experience
Madison, WI, 53704

Jamie is awesome! She went above and beyond our expectations while taking care of our boys!! She is very professional and took the time to meet the boys before our scheduled dates with her. We got great pictures from her!! We will definitely be using her again

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Megan R.
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: 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: Jessica B.
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Jessica B.
from
$15
per walk
5.0 out of 5 stars
13 reviews
10 years of experience
Middleton, WI, 53562

About: As a veterinary technician of 10 years, I have skills in administering medications, knowing when your fur baby is not feeling well or in pain, assisting senior fur babies in mobility or other needs and creating as stress free of an environment as possible. I work full time at a veterinary hospital. My work days are 10 hour days and 4 days a week. Before I leave for the day, I ensure fur babies are comfortable, well taken care of and receive lots of love before leaving. Once I am back, I immediately take care of fur babies, then spend time with them before everyone heads to bed. I treat every fur baby as if they were my own so get ready for lots of pictures, videos and updates! I highly value pet safety and ensuring they are as stress free as possible. I treat every fur baby as if they were my own and they are my priority before I takd care of anything else around the house or leave for work, and when I am back.

Sitter Profile Image: Cloey D.
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Cloey D.
from
$16
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
9 years of experience
Middleton, WI, 53562

Cloey did such a great job walking our dog Lily! She was timely and communicative. Lily got bored with walking so Cloey filled up the remaining time playing with her in the backyard. Lily loved her time with Cloey. Would recommend her to anyone!

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Jessica M.
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The median cost per walk for dog walking in Middleton is $20

Dog parents share their Rover experiences - Middleton

1 / 1
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

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

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

It is so comforting to know that Stina is giving my puppy love and a nice long walk while I’m away from home.

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Judy C.
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

Stefanie was so great with our dog—it was clear during the meet and greet that he felt comfortable with her very quickly. Communication was also great. We are very fortunate to have found her!

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Megan S.
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

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
5.0 out of 5 stars

Marianne provided great updates during her walks and was very communicative! She made sure our sweet, nervous boy was taken care of, and eased all our worries! Will be booking again!

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Margie E.
Dog Walking
5.0 out of 5 stars

He and his partner have been absolutely awesome with Gimli! Very communicative and friendly. I get home from work and Gimli seems so well taken care of. Definitely will book again.

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Gracelyn F.
Dog Walking
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Sitters in Middleton average 3
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FAQs for Dog Walking - Middleton

Frequently asked questions about Rover

The average cost for Dog Walking in Middleton on Rover is $22.2 per walk (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of August 2026, there are 1,415 sitters on Rover offering Dog Walking across Middleton. 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 Middleton. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Middleton.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Middleton. On Rover:

  • 91% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 98% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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