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: Kam O.
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Kam O.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 46 reviews
21 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: Cayla M.
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Cayla M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 35 reviews
14 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: Sally W.
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Sally W.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 6 reviews
2 repeat clients
20 years of experience
Waterford, WI, 53185

“We are so blessed to have found Sally. She has been so patient with Sasha. She can be timid but she is opening up and finially went on a full walk with Sally. Thank you so much for being here for her so we could enjoy our event away from the house and not worry about our girl.”

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Heather Z.
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: 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: Skyler B.
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Skyler B.
from
$25
per walk
10 years of experience
Wind Lake, WI, 53185

About: Growing up I had a dog and cat so already have experience plus I have dog sat for numerous of my parents friends and have always gotten good feedback from them. I am currently taking a semester off from college to work and save money I work at a daycare part time and am looking for extra ways to make money! I cannot do it at my home due to staying with family but being at your home the pets already know the environment and won’t need to learn anything and will be comfortable in a place they know.

Sitter Profile Image: Katie P.
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Katie P.
from
$20
per walk
5.0 out of 5 stars
• 28 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
• 5 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: Joseph M.
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Joseph M.
from
$16
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
5 years of experience
Waukesha, WI, 53188

About: I have taken care of dogs since a very young age.. I am experienced with dogs I’ve worked with dogs in the past as well as worked at doggy daycares/vets in the past. My schedule is relatively open so even if you need someone to come and walk the dog a couple times a day I can do that! I have experience with giving dogs medication and am able to help out with that as well. I watched a few dogs in the past that were seniors and needed special care with meds so I have experience in that category:) at the moment i am not working so this actually works out very well with me im relatively open for pet care:) i just have a few scattered doctors appointments throughout the week in my clients home I will make sure to follow any rules and or guidelines that are expected of the animals and myself obviously as I am in someone else’s home..

Sitter Profile Image: Isaiah H.
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Isaiah H.
from
$20
per walk
5.0 out of 5 stars
• 24 reviews
4 repeat clients
3 years of experience
Waukesha, WI, 53188

“He came right on time and even took the time to play with my little pup!”

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Klaudia A.
Sitter Profile Image: Tara R.
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Tara R.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
• 87 reviews
21 repeat clients
20 years of experience
Delafield, WI, 53018

“I had to change the date last minute and Tara was extremely understanding and responded to the new date within minutes. She’s arrived early to meet Jax and stayed later to play with him. I appreciated the extra time she spent with him and he didn’t want her to leave”

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Christine C.
Sitter Profile Image: Fatima B.
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Fatima B.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 9 reviews
2 repeat clients
2 years of experience
West Allis, WI, 53214

About: I am a dedicated pet caregiver committed to keeping your furry friend happy, healthy, and safe. I will strictly follow your pet's specific daily feeding and medication schedules to maintain their comforting routine. As an experienced and enthusiastic walker, I ensure they get plenty of exercise, fresh air, and fun outdoor adventures. Your pet will receive attentive, loving care and the absolute highest quality companionship every single day. I am a teacher so my schedule during the weekdays are from 8am-4pm. On the weekends I’m available all day. Feel welcome to send me a message! I will always follow the instructions that the pet owner gives me. Hiring me your pet will always be fed on schedule, enjoy play time, and treats. Every home I visit will be respected and well taken care of.

Sitter Profile Image: Heather H.
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Heather H.
from
$25
per walk
5.0 out of 5 stars
• 56 reviews
16 repeat clients
25 years of experience
Pewaukee, WI, 53072

“Heather was fantastic! She knew how to handle my young, strong Doberman with ease. I will definitely use her again to walk my boy and recommend her to family and friends. Thanks again Heather!”

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Julie C.
Sitter Profile Image: Michaela K.
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Michaela K.
from
$20
per walk
5.0 out of 5 stars
• 11 reviews
4 repeat clients
3 years of experience
Bluemound Heights, Milwaukee, WI, 53213

“Michaela took great care of Sadie Grace! She was reliable and communicated well. I would recommend her for your pup’s care”

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Mary
Sitter Profile Image: Jeremy W.
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Jeremy W.
from
$20
per walk
20 years of experience
Union Grove, WI, 53182

About: I’ve spent a majority of my life around animals. Growing up, we had a variety in the house (dogs, cats, fish, squirrels). I’ve learned that being calm, loving, and patient is the key to dealing with any pet. Like people, pets have their own quirks and personalities that is an absolute joy to learn about! I currently assist my sister with her two boys. Now that they are both in school, my schedule is much more open. I help get them to school early in the morning, and help pick them up in the afternoon. I have no problem helping with specialty pet needs and care, whether that be crating, medications, or assisted devices. Your pets are in great hands :)

Sitter Profile Image: Hannah S.
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Hannah S.
from
$20
per walk
5.0 out of 5 stars
• 136 reviews
5 repeat clients
4 years of experience
Menomonee Falls, WI, 53051

“Hannah was great! Took the time with our puppy and excited for her to walk him on a regular basis.”

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Bridget H.
Sitter Profile Image: Lexie R.
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Lexie R.
from
$20
per walk
1 repeat client
12 years of experience
Sherman Park, Milwaukee, WI, 53210

About: Are used to take care of cats, dogs, and horses for as long as I can remember. My neighbors would always have me careful there’s. I have a lot of free time, so I normally take my dog on a walk or run every day. Let’s go on an adventure. I have a fenced in backyard. I have a spacious home. I live in a very quiet neighborhood. Always give them love and attention that they need.

Sitter Profile Image: Lilyia S.
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Lilyia S.
from
$20
per walk
5.0 out of 5 stars
• 58 reviews
13 repeat clients
18 years of experience
Bay View, Milwaukee, WI, 53207

“Lilyia is great! She was always punctual and responsive for all of my bookings.”

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Kaitlyn T.
Sitter Profile Image: Trevor G.
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Trevor G.
from
$16
per walk
24 years of experience
Milwaukee, WI, 53220

About: I’ve worked with animals my entire life, growing up with pets to helping neighbors, family, and friends with pets. I have worked in pet stores and vet clinics and lots of pet sitting! I work at a school part time and I am looking for a side hustle that I will enjoy and love during the summer while school is out and even when school is back! I am super open for the next month or two! I make sure all the needs given by the owner is done efficiently and thoroughly as well as giving the love and affection needed for the pet!

Sitter Profile Image: Brittany D.
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Brittany D.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
2 repeat clients
5 years of experience
Milwaukee, WI, 53226

“Brittany is sweet, responsible, and caring. We love booking her for walks when we aren't home. She is trustworthy and great with our pup. Would definitely recommend!”

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

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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.

  • World-class support

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

How to book dog walking

  1. 1. Search

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

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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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 November 2026, there are 2,344 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 Caldwell. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Caldwell after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the 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:

  • 88% of walkers can help with special care needs
  • 94% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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