Dog Walking Caldwell

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Caldwell, 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: Tami G.
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Tami G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
70 reviews
14 repeat clients
4 years of experience
Waukesha, WI, 53189

Tami did an outstanding job! Sam just loved her! When he saw her car pull up the driveway he went "just nuts!" :-) Thank you Tami.

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Gleda D.
Sitter Profile Image: Carly B.
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Carly B.
from
$15
per walk
5.0 out of 5 stars
20 reviews
4 repeat clients
15 years of experience
Mukwonago, WI, 53149

Carly was great! My pup loved her and we had no issues! She was very efficient, kind and trustworthy!

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Jessica M.
Sitter Profile Image: Brandi W.
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Brandi W.
from
$20
per walk
5.0 out of 5 stars
21 reviews
6 repeat clients
8 years of experience
Mukwonago, WI, 53149

About: Hi! I have taken care of cats, dogs, chickens & lizards. I feed them, enjoy walking them & spending time with all of them. Thanks. I currently work full time and this is something I do part time, on the side. My full time job is flexible but I would need notice to adjust my work schedule.I can’t promise I can do this all the time… I like to do a meet n greet first so I can meet the family, let the pets sniff me & have some interaction. I follow the regular routine when I am in the clients home. If they are crated, I crate them. If they need to be let out in the middle of night & that is what the owner does, I let pet out…I make sure they are well taken care of. I treat them as they are my own.

Sitter Profile Image: Kam O.
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Kam O.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
42 reviews
20 repeat clients
20 years of experience
Waterford, WI, 53185

Kam has been great to work with and brings peace of mind. She is prompt and reliable for our regular walks! We are thankful to have her take care of our Lexi.

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Rhonda M.
Sitter Profile Image: Cayla M.
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Cayla M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
29 reviews
8 repeat clients
25 years of experience
Burlington, WI, 53105

Cayla is an amazing dog caretaker! She has a genuine love for animals, and it is apparent in her interactions with them. My dog is my baby, there is not many people besides my family and closest friends I trust with him, but Cayla is someone I can say I truly trust to take the best care of my pup! She makes each animal feel loved and special. I would very highly recommend Cayla!

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Janelle M.
Sitter Profile Image: Carrie B.
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Carrie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
47 reviews
13 repeat clients
25 years of experience
Mukwonago, WI, 53149

We use Carrie to let our dog out while at work and we couldn’t recommend her more!! This was our first time using Rover and we are so glad we found her. She is reliable, a great communication and we love the photos we get from her. It is nice knowing our pup, Woody, is in good hands when she goes to take him on walks. You can tell Woody loves her as well. 10/10 recommend Carrie!!

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Rylee H.
Sitter Profile Image: Lydia M.
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Lydia M.
from
$22
per walk
5.0 out of 5 stars
4 reviews
1 year of experience
Big Bend, WI, 53103

About: I volunteer at a dog shelter that deals with all ages and comfortably around new people. This allows me to pick up on dogs needs and adjust accordingly. I am currently working full time 4 days a week. This allows me a more flexible schedule to help take care of dogs through the week and weekends. I have experience with dogs that bolt when doors are opened outside and know how to block them properly. When helping with potting breaks they can be play breaks to get rid of excess energy. I have experienced teaching dogs to walk on a leash with and without a harness.

Sitter Profile Image: Diane R.
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Diane R.
from
$20
per walk
4.4 out of 5 stars
18 reviews
7 repeat clients
30 years of experience
Big Bend, WI, 53103

About: I have taken care of a menagerie if pets my entire life. Family, friends, and neighbors have trusted me to care for their furbabies. I will give your pets the love and attention they deserve I currently work part time in the evenings so I have plenty of time to take care of your pets. I am available weekdays, weekends, and holidays. I will care for your furbabies in your home so they are in a familiar place and reduce stress. I will care for them as if they were my own. Giving them play and exercise keeping to their schedule and routine.

Sitter Profile Image: Ashley M.
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Ashley M.
from
$20
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Mukwonago, WI, 53149

About: I’ve grown up around dogs my entire life and as a pet owner myself, I know how important it is to have care that can be trusted. I’ve taken care of dogs of all shapes and sizes for family and friends in the past. I am committed to giving the best care to all of our furry friends and guarantee to treat them like my own. My schedule is currently open most of the time so I can be very flexible when it comes to working with you and your pet’s busy schedules. I am happy to follow any special instructions you may have related to feeding, medication, or any other pet needs that are requested by you.

Sitter Profile Image: Morgan S.
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Morgan S.
from
$21
per walk
5.0 out of 5 stars
33 reviews
4 repeat clients
10 years of experience
East Troy, WI, 53120

Thanks so much!

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Angela P.
Sitter Profile Image: Madylin L.
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Madylin L.
from
$15
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Waterford, WI, 53185

About: I had 2 cats and a dog growing up! No pets currently but happy to play and take care of yours! Currently cannot watch any pets at my home but happy to complete as many home visits as necessary as long as you are relatively close by:) I am not currently working full time and my schedule is fairly flexible. I am happy to discuss any extra care needed for your pet. I am happy to follow specific instructions/feeding schedules as needed. I will also completed any necessary home care tasks as wanted as long as discussed prior.

Sitter Profile Image: Katherine S.
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Katherine S.
from
$20
per walk
5.0 out of 5 stars
2 reviews
10 years of experience
Waukesha, WI, 53189

About: Animal lover with a passion for providing safe, loving care. I’ll make sure your pet gets plenty of attention, affection, and fun while you’re away. I work remotely part time, which allows me flexibility throughout the day. My schedule does vary, but I generally have availability at different times for visits, walks, and pet care throughout the day and early evening. Your pet’s comfort and happiness are my top priorities. I’ll come to your home to provide personalized care while keeping their routine as familiar as possible. As a pet owner, I know how much trust it takes to leave your pets with someone else, so I’ll follow all directions, send plenty of pictures and updates, and treat your pet like they’re my own.

Sitter Profile Image: Kayla B.
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Kayla B.
from
$25
per walk
5.0 out of 5 stars
3 reviews
15 years of experience
Mukwonago, WI, 53149

About: Having a furry friend in the home has been a norm for me for as long as I can remember! I’ve cared for dogs of my own and family members dogs for my whole life. I have trained my own family dog through 4-H, so I am knowledgeable on some training tactics for dogs, just let me know your furry friends needs! :) I am currently taking time away from work, so I am available full time to care for your pets! Whether you just need someone to take them on walks or you need a sitter for a vacation, I am available whenever you need! At home, I’m in an apartment with an indoor cat of my own. He loves to follow me around to house and be wherever I am!

Sitter Profile Image: Susana C.
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Susana C.
from
$20
per walk
5.0 out of 5 stars
31 reviews
7 repeat clients
15 years of experience
Eagle, WI, 53119

Susana was hired to be our dogsitter/walker during our daughter's wedding at a campground in East Troy, WI. She was asked to attend the wedding and help us with our Great Dane Molli who was part of the wedding party. Susana came out to us and stay by Molli's side for the time that we wanted to socialize with family and friends and eat dinner at the reception. Molli seemed to really like Susana and was super comfortable with her immediately. We will definitely consider having Susana help us with Molli next time we are staying in the East Troy/Lake Geneva area.

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Kelly B.
Sitter Profile Image: Sally W.
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Sally W.
from
$15
per walk
20 years of experience
Waterford, WI, 53185

About: I have had dogs as pets since a child and love animals of any kind. I have cared for dogs and cats along with dog walking for many years, including puppies and reactive dogs. I have a reactive dog myself and have experience walking and caring for reactive and anxious dogs. I have experience with a prong collar. Your pet will be my main focus and priority and I will love them like my own. I am currently a stay at home mom and can be flexible with my schedule. Just let me know what you are looking for and I can make arrangements. I take care of animals like they are my own, they will have all of my focus and attention and love. Drop in visits and walking services available.

Sitter Profile Image: Chloe G.
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Chloe G.
from
$20
per walk
5.0 out of 5 stars
2 reviews
6 years of experience
East Troy, WI, 53120

About: I have had both cats and dogs since I was born and have lots of experience providing care for many ages, behaviors, and disabilities. Over the last few years, I have aided with foster dog care, and while it can be challenging, it is very rewarding. Over the last few years, I have seen seniors, puppies, and pregnant dogs come through the home, and I always try to provide the best care I can while trying to find homes that are a good fit! I am working a part-time job at Carthage College and have ample time to help provide care. During the weekdays, I am quite flexible with my availability. On weekends I have lots of flexibility as well in order to provide ample support and care for pets. I am very active, so I am more than willing to provide walks and activities for your pup! If your dog needs medication, I am able to administer it when needed. I can also provide time outside and around the home if the dog must be in a crate.

Sitter Profile Image: Kelsey H.
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Kelsey H.
from
$20
per walk
8 years of experience
Burlington, WI, 53105

About: Hi, I’m Kelsey! I’ve been around dogs my entire life and have always had a special connection with them. Growing up with dogs taught me the importance of patience, responsibility, and providing pets with the love and care they deserve. I have a dog of my own, so I understand how important it is to find someone you can trust with your pet. I know how much pets mean to their families and will always make sure they feel safe, comfortable, and loved while they’re in my care. I enjoy spending time with dogs, whether it’s going on walks, playing, keeping them company, or simply making sure they feel loved and cared for while you’re away. Every dog has their own personality and needs, and I’m excited to get to know yours. I’ll treat your pet with the same care and affection I give my own and would love the chance to help keep them happy, safe, and comfortable. I am available Monday through Sunday at any time and have a flexible schedule to accommodate your pet’s needs. Whether your furry friend needs early morning walks, daytime check-ins, evening visits, or overnight care, I am happy to work with your schedule. I will care for your pet in your home by keeping them comfortable, safe, and following their normal routine as closely as possible. I understand that pets feel most secure in a familiar environment, so I’ll provide plenty of attention, affection, playtime, and companionship while you’re away. I will follow your instructions for feeding, walks, medications (if needed), and any special preferences your pet may have. I’ll make sure they receive the care and attention they need, while also respecting your home and keeping you updated with photos and messages so you can feel confident that your pet is happy and well cared for.

Sitter Profile Image: Tami R.
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Tami R.
from
$16
per walk
35 years of experience
Mukwonago, WI, 53149

About: 75% of my life has been spent with dogs. In 2017 and after saying goodbye to our 13 year old yellow lab, I brought home a 10 week old German Shepard/Border Collie mix. He is a rescue from Oklahoma. I trained, potty trained, raised and still love Bandit. Last November an 8 week old Catahoula Leopard mix from the WI Humane Society was added to the equation. Pirate and Bandit are best of friends. Before Pirate, Bandit was anxious, skidding, ran away from and would go to only a select few. Who knew all he needed was his own emotional support dog?! He is a completely different dog. Friendly, not skidding, loves to play and run. Pirate is the same size at a year old as Bandit (approx 65 lbs. each) I am partially retired which gives me the availability and flexibility to come, play and stay in your home. Specific days of availability are Tuesday, Thursday, Friday, Saturday and through Sunday mornings. My only goal is to provide World Class service to you and your pets. I am able to administer medications, feed, potty and any other general care needed in your absence.

Sitter Profile Image: Breonna B.
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Breonna B.
from
$12
per walk
1 year of experience
Mukwonago, WI, 53149

About: I’ve always had dogs and pets growing up and have been a sitter for many friends and family’s throughout the years! All types and ages and breeds I’m currently working part time so I’ll have plenty of time to time to play and hang out with your pups! Especially on weekends - Friday, Saturday, Sundays ! I will follow your instructions clearly for how you would like me to treat your pups/animals and your home. I value your privacy and respect your home.

Sitter Profile Image: Julia S.
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Julia S.
from
$20
per walk
5.0 out of 5 stars
11 reviews
4 repeat clients
5 years of experience
Mukwonago, WI, 53149

About: While I haven’t had a dog of my own, I’ve had the joy of dog sitting and caring for many over the years. I genuinely love spending time with dogs—whether it’s going for a walk, playing, or just giving them the love and attention they deserve. I make sure each dog feels safe, happy, and well cared for, just like they would at home. I currently work part-time from 3pm to 12am but my schedule will be changing late August to 8am-7pm full time. Your pets will always be in good hands as I am a huge animal person! I always prioritize making pets feel comfortable, safe, and loved—whether they’re in my home or their own. In a client’s home, I follow their usual routine as closely as possible, including feeding schedules, walks, playtime, and any special instructions. I also make sure to keep the space clean and secure. If caring for pets in my home, I provide a calm and pet-friendly environment with plenty of attention, enrichment, and affection. I treat every pet like they’re part of the family.

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

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Popular requests for dog walking - Caldwell

Select a filter and find qualifying sitters offering dog walking.

Sitters in Caldwell average 4
repeat dog walking clients

FAQs for Dog Walking - Caldwell

Frequently asked questions about Rover

As of July 2026, there are 2,567 sitters on Rover offering Dog Walking across Caldwell. 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 Caldwell. 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 Caldwell.

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 Caldwell. On Rover:

  • 92% of walkers can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% 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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