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: Carrie B.
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Carrie B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 60 reviews
20 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: Tami G.
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Tami G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 82 reviews
18 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: Morgan S.
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Morgan S.
from
$21
per walk
5.0 out of 5 stars
• 34 reviews
5 repeat clients
10 years of experience
East Troy, WI, 53120

“Thanks so much!”

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

“Kam has been very dependable and great with Riley. Today our camera caught her turning around to wave at him thru the window as she left the house. So cute!”

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Shannon H.
Sitter Profile Image: Sally W.
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Sally W.
from
$15
per walk
5.0 out of 5 stars
• 2 reviews
2 repeat clients
20 years of experience
Waterford, WI, 53185

“Sally is an absolute joy to work with! Flexible and willing. Jupiter was well taken care of :)”

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Sophia B.
Sitter Profile Image: Brandi W.
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Brandi W.
from
$20
per walk
5.0 out of 5 stars
• 22 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: Stephanie S.
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Stephanie S.
from
$20
per walk
4.9 out of 5 stars
• 65 reviews
25 repeat clients
28 years of experience
Mukwonago, WI, 53149

“Stephanie has cared for our golden retriever on 3 separate occasions. Her loving care for our dog, combined with her professionalism and excellent communication, are exemplary. We will call on Stephanie again in the future and recommend her in the highest terms possible.”

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Scott B.
Sitter Profile Image: Cayla M.
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Cayla M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 35 reviews
11 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: Emily D.
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Emily D.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 94 reviews
38 repeat clients
11 years of experience
Capitol, Burlington, WI, 53105

“Emily is a sweet woman who is definitely an animal lover! My dog fell in love with her and thoroughly enjoyed each walk they went on. I highly recommend Emily as she is dependable and will be wonderful with your fur baby!”

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Matt P.
Sitter Profile Image: Cali T.
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Cali T.
from
$12
per walk
5.0 out of 5 stars
• 22 reviews
11 repeat clients
7 years of experience
Waterford, WI, 53185

“Cali did a great job of walking Paddington! I look forward to the next time! Thank you!”

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Terri T.
Sitter Profile Image: Lydia M.
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Lydia M.
from
$22
per walk
5.0 out of 5 stars
• 6 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: Sydney M.
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Sydney M.
from
$16
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
10 years of experience
Muskego, WI, 53150

About: For the last 10 years I have been the go to pet-sitter for my family, friends and neighbors, and I can be for you also! I have a lot of experience with dogs of all sizes and cats of all kinds. I have taken care of itty bitty baby kittens and helped raised them up to go into their forever homes. I spent time working at a doggie daycare, where I gained some experience administering medications such as pills and eyedrops/eardrops. I, myself have three cats Roo, Gus and Noelle I am currently doing pet care full-time, and I can work with your schedule. I can be flexible, just let me know when you need me! With my own cats and I strive to take care of them the best I can, they get the best food, the best water, a lot of play and so many cuddles. I will take care of your babies as if they are my own, while also also sticking to your standards and routine.

Sitter Profile Image: Susana C.
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Susana C.
from
$20
per walk
5.0 out of 5 stars
• 33 reviews
8 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: Mandy & Jason W.
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Mandy & Jason W.
from
$15
per walk
5.0 out of 5 stars
• 84 reviews
8 repeat clients
10 years of experience
Burlington, WI, 53105

“Mandy is super flexible and Molly loves leaving with her for a walk. Mandy has been on time and professional.”

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Tricia C.
Sitter Profile Image: Madylin L.
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Madylin L.
from
$15
per walk
4.7 out of 5 stars
• 4 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
• 3 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: Jason B.
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Jason B.
from
$30
per walk
5.0 out of 5 stars
• 27 reviews
8 repeat clients
45 years of experience
Burlington, WI, 53105

About: I’m a guy who falls in love with dogs instantly. Don’t want them back? No worries! Dogs instantly want to be my best friend and I’ve never met a dog that I didn’t like or that didn’t like me. I work from home. My dogs are part of the family. I would take care of your dogs as if they were my own children. I have a doggy door and outside kennel for the dogs to use as needed. I’m also happy to take dogs on a walk and my wife is a super dog walker. We have two dogs-a Pomeranian who is all love and a lab who’s an old girl but who is the best dog you’ll ever meet. I understand dogs. How they communicate, how they operate. I know how to get them to develop good habits.

Sitter Profile Image: Katie P.
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Katie P.
from
$20
per walk
5.0 out of 5 stars
• 27 reviews
9 repeat clients
16 years of experience
Eagle, WI, 53119

“Katie is wonderful! She met Dobby and he loved her. I could tell she was a doggy person right away! She took great care of my fur baby, sent pics, updates, and was very flexible with her schedule. I will be using Katie again and again for our pups walks.”

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Deanna W.
Sitter Profile Image: Madelyn G.
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Madelyn G.
from
$15
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Raymond, WI, 53126

About: I've been around animals my whole life! Family and friends have trusted me to feed, walk, play with, and care for their pets, both cats and dogs. I also worked for Wag, which I thoroughly enjoyed and learned so much about caring for pets. My schedule is extremely flexible and I only work part time, so I can care for your pets at almost any time of day, especially mornings and afternoons. In a client's home, the pets are in a familiar environment with an unfamiliar person. So, the first thing I do is give the pets a chance to get used to me! Let them sniff me, let them approach me at their own pace.

Sitter Profile Image: Grace R.
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Grace R.
from
$14
per walk
5 years of experience
Waukesha, WI, 53186

About: I’ve been pet sitting my neighbors dogs since I was 15. This summer I spent 2 months in Greece taking care of 100+ pound dogs! I have plenty of experience giving animals their medicine and grooming if needed! I am a full time student majoring in Animal Behavior, with many gaps in my schedule to have enough time for your animal! I am the most free on the weekend but have time throughout the weekdays! As I am a student I do not have my family dog with me. However I would love to treat your dog as my own and care for them greatly!

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

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

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Popular requests for dog walking - Caldwell

Select a filter and find qualifying sitters offering dog walking.

Sitters in Caldwell average 3
repeat dog walking clients

FAQs for Dog Walking - Caldwell

Frequently asked questions about Rover

As of September 2026, there are 2,409 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
  • 96% 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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