Dog Walking Woodland

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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: Kathleen G.
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Kathleen G.
from
$10
per walk
5.0 out of 5 stars
• 13 reviews
3 repeat clients
7 years of experience
Mayville, WI, 53050

About: I’ve had dogs my whole life, but in my adult life I’ve gotten my own 3 labs. They are so special to me and I treat them like my children. I am home all day, (I work remotely) so I am able to keep an eye on your pets 24/7! If I had your dog(s) here they’d get treated the same way as my own babies. We all love to go on long energizing walks, but if your dog prefers to walk alone I can do that too! I currently work full time remotely 8-4:30, so it is very easy for me to keep and eye on your pets! I am fully available on the weekends as well. (Per schedule) I have 3 SUPER friendly dogs, they are very big hits at the dog park. I do sleep with them and allow them on the furniture. I can easily crate a dog if needed as I have 3 that I used for my dogs that they do not need anymore. I don’t have a fenced in yard as my dogs have an invisible fence, but they don’t get let out unsupervised and I do have a lead/chain that I can attach to my back deck.

Sitter Profile Image: Brandi K.
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Brandi K.
from
$12
per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
4 years of experience
Hartford, WI, 53027

“Brandi was great with my 3 dogs. She was on time. Was able to meet the dogs and I before the first day. There was an issue with the neighbors dog jumping my fence when she was out with my 3 dogs. She handled the situation very well! She sent me a lot of pictures also! I would have Brandi come back and take care of my dogs again!.”

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Teresa S.
Sitter Profile Image: Mary C.
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Mary C.
from
$20
per walk
5.0 out of 5 stars
• 8 reviews
30 years of experience
Watertown, WI, 53098

About: Had cats all my life and dogs for last 12 years. Animals have a sixth sense about people and I'm one of those they seek out for rubs, cuddles, playtime, snacks and love... Im available anytime currently. This has no chance of changing within the next few months so please give me a hello and let's see if I can help you. I will only be able to care for pets at your home as we currently have 2 cats (one who is very persnickedy). Lost our boxer and Irish wolfhound in the last few months. So really hoping to find some dogs to ease my broken heart.

Sitter Profile Image: Anna H.
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Anna H.
from
$25
per walk
5.0 out of 5 stars
• 6 reviews
3 repeat clients
12 years of experience
Oconomowoc, WI, 53066

“Anna took the best care of Winston! Our puppy can be shy and nervous, but she treats him like one of her own regardless and we are so thankful to have her spend time with him while we are at work. Thank you again Anna!”

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Kristen M.
Sitter Profile Image: Mary A.
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Mary A.
from
$50
per walk
5.0 out of 5 stars
• 3 reviews
30 years of experience
Hartford, WI, 53027

About: Dog owner x 30years. Had 2 dogs x 10 years, otherwise only 1 dog. Dogs enjoyed family adventures. Currently enjoying being a Grandma to my Grand pastor and foster pups Working part-time as RN, Jazzercise and caregiver for seniors. Schedule flexible. Have a SUV that I can transport dog to the dog park if desired. I use a long leash for yard. Enjoy walking dogs on heel when in residential areas. Enjoy the variety of parks, hiking trails and water in my neighborhood.

Sitter Profile Image: Savannah B.
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Savannah B.
from
$20
per walk
10 years of experience
Lomira, WI, 53091

About: As far as experience goes there isn’t a time in my life I remember that I wasn’t caring for an animal. From reptiles, to rodents, to cats and dogs, I’ve had them all. From a young age I was taught responsibility and discipline when it came to caring for tiny creatures. Additionally for over two years I volunteered weekly at a local animal shelter. During this time I gained knowledge as to how animals interacted with one another, how to properly administer medication, warning signs to look out for, what to do in emergencies, and deeply studied animal behavior. To add on to that I am currently employed at a doggie daycare. During my time here not only have I gotten to widen my horizons when it came to taking care of animals but I have learned hands on how to bandage a wound, what to do in animal confrontations as well as how to handle the unexpected such as sickness or seizures. Additionally over the last 3 years I have volunteered at different animal welfare programs across the globe. These include Portugal, Puerto Rico, Tanzania and soon Hawaii. During this time I have not only seen hands on other cultures way of taking care of animals but also gained knowledge as to how to better the animal care I provide to clients. As I previously stated I currently am employed at a doggie daycare. Additionally I work at a bakery as well. My schedule changes weekly so it can be hard to give an exact time frame when booking. Typically I work up to 8 hour shifts. I typically prefer to stay in clients homes to keep their pets safe and happy in their own environment. I will be there in the morning before work, and will immediately come back when I get off as well as being there at night. I try to spend as much time as possible with the pets while you are away I typically only offer staying in the clients home and I am comfortable crating animals while gone. I always keep things like medications safely out of reach and secured. Additionally upon booking I typically ask about any health notes, allergies, or special needs as well as a good contact number for your vet in case of emergency.

Sitter Profile Image: Alexandria M.
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Alexandria M.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
• 49 reviews
17 repeat clients
10 years of experience
Oconomowoc, WI, 53066

“On time and super nice!! Highly recommend Alex she definitely tired Yeli out☺️”

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Elizabeth W.
Sitter Profile Image: Raegan S.
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Raegan S.
from
$25
per walk
5.0 out of 5 stars
• 2 reviews
9 years of experience
Oconomowoc, WI, 53066

About: I’ve take care of dogs my whole life. I’ve taken care of puppy’s to senior dogs. I groom, clean up, and shower them in love I work part time but have a bunch of free time to take care of dogs. I am commuting to college so when school starts but I still have plenty of time to take care of dogs I always show dogs love and give them space when needed. I have two dogs and many more before that, so I have experience with dog behavior

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: Erin N.
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Erin N.
from
$19
per walk
5.0 out of 5 stars
• 28 reviews
2 repeat clients
3 years of experience
Wauwatosa, WI, 53226

“Carter definitely had a blast walking with Erin! Thank you very much”

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Beatriz A.
Sitter Profile Image: Maxwell W.
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Maxwell W.
from
$20
per walk
5 years of experience
West Allis, WI, 53214

About: I’ve grown up caring for cats and dogs and have always enjoyed spending time with animals. I have an active dog of my own who loves going on long walks, so I’m very comfortable keeping energetic dogs active and entertained. As a high-level athlete, I’m active myself and genuinely enjoy being outdoors, whether that’s walking, playing, or simply spending time with a pet. I’ve also helped neighbors care for their animals while they were away. Right now I’m training in Milwaukee and have practice at 3:30 so I can take care of your pet during the day but also after practice if needed. Would be preferred if I did at the clients house but I live in a apartment right now they have a dog park and sorts.

Sitter Profile Image: Alex M.
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Alex M.
from
$30
per walk
4.6 out of 5 stars
• 83 reviews
19 repeat clients
10 years of experience
Cudahy, WI, 53110

“Alex is reliable, dependable, and flexible dog walker. She’s been able to get our dog to go to the bathroom on walks (our dog always refused before) and to start loose leash walking. Lily loves Alex and waits at the front door for Alex to pick her up on walk days. I highly recommend Alex!”

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Sarah O.
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The median cost per walk for dog walking in Woodland is $20

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How to book dog walking

  1. 1. Search

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    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for dog walking - Woodland

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Sitters in Woodland average 4
repeat dog walking clients

FAQs for Dog Walking - Woodland

Frequently asked questions about Rover

As of October 2026, there are 769 sitters on Rover offering Dog Walking across Woodland. 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 Woodland. 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 , 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 Woodland 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 , 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 .

Yes, you can find walkers who have experience with handling special pet needs in Woodland. On Rover:

  • 88% of walkers can help with special care needs
  • 94% 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 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 .

walkers on Rover set their own , 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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