Dog Sitting Greendale

Book a Greendale dog sitter to watch your dog in your sitter’s home or yours.

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Over 74
pet parents in Greendale have booked dog sitting

Greendale, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Bill B.
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Bill B.
from
$20
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
20 years of experience
Greendale wi, WI, 53129

About: I have many years of experience caring for and training my own pets and fostering a few along the way. I am an avid rescuer and love taking care of animals from all walks of life. High energy, elderly, barkers, wigglers even the stinky are welcome. I take pride in providing care for your pet. Cheers! I work full time but can stop by and walk before or after work. Morning and nights are available, hoping to go full time soon. We currently are pet free after a difficult and sudden passing but we have a woodsy backyard and a grassy front yard that a pooch can get some good exercise in. Two teenage boys to help with playtime and wife that loves to take dogs for jogs.

Sitter Profile Image: Elizabeth H.
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Elizabeth H.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
217 reviews
40 repeat clients
9 years of experience
Muskego, WI, 53150

Elizabeth exceeded our expectations in every way. She went above and beyond to make sure our pups were well cared for and well-loved. We are already repeat customers, and we will definitely be contacting her again!!

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Annette Lovrien D.
Sitter Profile Image: Jessi C.
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Jessi C.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
295 reviews
79 repeat clients
38 years of experience
New Berlin, WI, 53151

We had a great experience with Jessi. She was very friendly and loved out cats while we were gone for a few days. Great communication too - highly recommend!!

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Lisa G.
Sitter Profile Image: Cindi W.
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Cindi W.
from
$17
per visit
10 years of experience
Franklin, WI, 53132

About: I love animals and have always had them. My friends reach out to me for pet sitting because they know I will take the best care of their fur babies! I have a teacup Yorkie and a cat so if you have a friendly pet, they are welcome to stay by me, but I am also retired so can stay by you if that's more convenient. I am very flexible! I am retired so have all day & evening to spend with your fur babies. I love to walk so would be sure to take your fur babies outside for fresh air any time of the year. I live in a safe area and have beautiful paths for dog walking any time of day. If your pet likes car rides, I love the beach & the water so could have lots of fun taking them wherever they like to go!

Sitter Profile Image: Kelsey S.
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Kelsey S.
from
$25
per visit
5.0 out of 5 stars
20 reviews
5 repeat clients
5 years of experience
Hales Corners, WI, 53130

Kelsey was fantastic with my nervous pup. She gave him the space he needed, but got him to eat dinner, and he even relaxed on the couch while I was gone, which is rare for him. She kept me updated all night and was very communicative. I'm looking forward to using Kelsey's services in the future!

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Keara P.
Sitter Profile Image: Stephany N.
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Stephany N.
from
$18
per visit
5.0 out of 5 stars
6 reviews
15 years of experience
Milwaukee, WI, 53219

About: I am new to Rover and looking forward to providing the best care for your loved one. I have worked with dogs through shelters and personal pet sitting for family and friends. I am new to Rover and work part-time with animals. I am available for pet sitting, walks and drop-ins during the weekends all day and with some flexibility during weekdays. We can discuss boarding on a case by case basis. I will follow the owner's guidelines and treat your house and pets with respect. I use a common sense approach to safety and will stay vigilante when spending time with your loved one. I believe in clear communication and am happy to update you as much as needed. Thank you allowing me to help relieve some of the petcare duties for your dog or cat. My personal goal is to keep your pet comfortable and happy while you are away!

Sitter Profile Image: Bella E.
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Bella E.
from
$14
per visit
10 years of experience
Hales Corners, WI, 53130

About: I’ve taken care of animals longer than I’ve even been working. Animals have been a big part of my life and I know it’s a big part of everyone’s. My experience with dogs are more close to big dogs, hunting dogs, and pittbulls. However I’ve also puppy-sat and dog sat small dogs before. And while I don’t want to puppy sit again, I’d love to dog sit! I love giving dogs enrichment activities on walks and at home. So they will never be bored with me! Currently my day life is a bit messy. So I won’t divulge too much. But my mornings I like to keep to myself since this is the first time in years I’ve had slow mornings. But I’m such a night owl that anything after 3pm works!! My house doesn’t have a fence, which is why I currently don’t offer at my house services. But I did however train one of my dogs to be off leash with a good recall! The other won’t be allowed to do so. He chases squirrels wayyyy too much!

Sitter Profile Image: Berenice B.
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Berenice B.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
270 reviews
111 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

Berenice was consistent and kept my cats from guessing at what time they will eat and get some cuddles. I appreciate this because they do not like change. She communicated via Rover only which was a bit hard because of where we were so next time I will insist on getting texts instead if possible. She was also very responsive when I asked her to do something.

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Vanessa N.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
121 reviews
34 repeat clients
40 years of experience
West Allis, WI, 53227

This is Sadie’s first visit with Jenn and everything went so well. She was prompt, had quality time with Sadie and accomplished everything discussed. Jenn is very reliable and I would highly recommend her.

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Tonya B.
Sitter Profile Image: Justine R.
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Justine R.
from
$20
per visit
5.0 out of 5 stars
6 reviews
20 years of experience
Euclid Park, Milwaukee, WI, 53227

About: I’ve been a devoted animal lover and pet owner for as long as I can remember. From dogs and cats to caring for pets with unique personalities and needs, animals have always been a huge part of my life. Currently, I share my home with a lovable, mischievous hound mix who keeps me on my toes and a cat who completely stole my heart. A few years ago, I lost my soul dog, Jersey, and that experience deepened my understanding of the special bond we share with our pets. I know firsthand how difficult it can be to leave them behind and trust someone else with their care. That’s why I treat every pet as if they were my own—with patience, affection, attention, and plenty of love. Whether your pet needs a quick drop-in visit, playtime, cuddles, a walk, or simply a friendly face while you’re away, my goal is to make them feel safe, happy, and cared for. I also know how important peace of mind is for pet parents, so you can expect regular updates, photos, and communication throughout my visits. Because I work from home, I have a flexible schedule that often allows me to accommodate drop-in visits and pet care needs throughout the day. I’m committed to providing dependable, compassionate care and building a trusting relationship with both you and your pets. I look forward to meeting your furry family members and becoming someone you can count on whenever you need a helping hand! 🐾❤️ I work from home and have a decently flexible schedule. I have a young son and pets of my own but thankfully I share these responsibilities with my rockstar husband so I will be able to care for your fur babies. I understand that having a stranger in your home can be a little uncomfortable. I will 💯 respect your space and keep things clean in order for your while you are gone. Please let me know your preferences for my stay.

Sitter Profile Image: Maya M.
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Maya M.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
10 years of experience
Greenfield, WI, 53228

Maya was excellent with Rosie and Rudy. I knew they were well cared for while I was away, which gave me peace of mind during my travels!

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Emily A.
Sitter Profile Image: Leslie H.
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Leslie H.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Greenfield, WI, 53221

Leslie is a compassionate animal lover who provided outstanding care for my cat. She always had great communication, providing plenty of adorable photos and thorough updates. She is detail-oriented, going above and beyond to make sure all of our pet and home-related needs are met. Knowing I had someone so genuine and reliable looking after my pet and home was a huge peace of mind. I came back home to a happy, satisfied cat and a clean space with everything left in place. It's such a comfort and relief to find such a trustworthy and exceptionally amazing pet sitter. I would highly recommend her for any animal care needs!

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Aj M.
Sitter Profile Image: Jackie H.
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Jackie H.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
76 reviews
24 repeat clients
36 years of experience
Muskego, WI, 53150

Jackie is wonderful with her care for our dogs and ease in scheduling! She’s been helping us for a month now and we always come home to happy pups!

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Kim F.
Sitter Profile Image: Rachel P.
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Rachel P.
from
$15
per visit
20 years of experience
New Berlin, WI, 53151

About: I love animals. I've taken care of multiple dogs and cats throughout my life. My two cats, Prim and Khaleesi, are my world! I have experience with large and small dogs, as well as volunteer experience at the Oakland County Animal Shelter in Michigan. I've cared for energetic pups all the way to senior dogs that can't use the steps anymore. Being a stay-at-home cat mom, I have a flexible schedule that allows me to visit at consistent, predictable times. I use a car as transportation, so I can get there reliably. I treat every booking as a commitment, not just a task, so you can count on me to show up on time and follow the care routine exactly as you've set it out. My own pets are fed twice a day, and have their water bowl cleaned and refilled once a day. I can co-exist with your pet, or play with them for 30 minutes, whatever they need!

Sitter Profile Image: Marilia D.
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Marilia D.
from
$25
per visit
5.0 out of 5 stars
83 reviews
26 repeat clients
15 years of experience
Wilson Park, Milwaukee, WI, 53221

Marilia is very thorough and professional in the way she conducts herself. From scheduling a meet-and-greet to setting up a time to pick up the house key, she made sure all the details were taken care of. On the days that she popped in to feed our cats she promptly sent photos of and comments about the things we asked her to do. Our kitties were happily waiting for us when we returned from our trip, well fed and in good spirits. We will be comfortable and confident when we hire Marilia again for future bookings. Holly & Sid W.

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Holly W.
Sitter Profile Image: Julia R.
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Julia R.
from
$23
per visit
5.0 out of 5 stars
22 reviews
7 repeat clients
2 years of experience
Cudahy, WI, 53110

Julia has been SUCH a huge help to me with my dog Payton. She’s very responsive, reliable, kind, sends the cutest pics while I’m away at work and takes amazing care of P. I would recommend her for any service you may need :)

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Katie S.
Sitter Profile Image: Anna S.
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Anna S.
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Oak creek, WI, 53154

Anna is the best and took great care of my dog, Sammy! Sammy loves her very much and looks so happy in all his photos!

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Andy P.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$20
per visit
5.0 out of 5 stars
13 reviews
1 repeat client
16 years of experience
Alverno, Milwaukee, WI, 53220

About: My unconditional love for all animals. Every cat or dog that I meet I treat and cherish as if they were my own fur baby. I do work a full time job, 8-4 Mon-Fri. However, I am looking to use some of my free time taking care of your fur baby! I do my best to maintain whatever routine you have with your fur baby. I am willing to go the extra mile to make your pup feel safe and comfortable while you are away.

Sitter Profile Image: Alexandra F.
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Alexandra F.
from
$20
per visit
5.0 out of 5 stars
32 reviews
7 repeat clients
25 years of experience
Franklin, WI, 53132

Alex was great! We knew our cats were well taken care of and got lots of love while we were gone. She did a great job with everything, including their complicated feeding routine. We also appreciate the updates and pictures while we were gone. Will definitely book her again!

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Jill H.
Sitter Profile Image: Angie B.
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Angie B.
from
$20
per visit
5.0 out of 5 stars
35 reviews
10 repeat clients
30 years of experience
West Allis, WI, 53219

Angie was wonderful with communication and photos. I would highly recommend and would use again. Thank you!

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Becky D.
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The median cost per visit for dog sitting in Greendale is $20

Dog parents share their Rover experiences - Greendale

1 / 1
5.0 out of 5 stars

So glad everyone got along for the first drop-in. Leandrea was very good with communication. Look forward to next time.

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Traci B.
Drop-In Visits
5.0 out of 5 stars

Amanda has been great to work with and she handled the craziness of our two four month old puppies wonderfully! She is great at communicating and provided a nice summary of her visit along with some pictures. We look forward to having Amanda watch the dogs again.

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Stephen M.
Drop-In Visits
5.0 out of 5 stars

Was able to accommodate a last-minute booking due to unexpected surgery and was super-accommodating over the weekend hospital stay updates. The pups looked super happy in every pic! Thanks so much.

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Dave B.
Drop-In Visits
5.0 out of 5 stars

Maya was excellent with Rosie and Rudy. I knew they were well cared for while I was away, which gave me peace of mind during my travels!

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Emily A.
Drop-In Visits
5.0 out of 5 stars

Stephanie was great! She was responsive and communicative and I was able to be worry-free when out of town!

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Cheryl E.
Drop-In Visits
5.0 out of 5 stars

Always responsive and attentive to the needs of Winnie and Moose. We are so glad we have found a sitter we can trust and that the pets love to see!

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Julia M.
Drop-In Visits
5.0 out of 5 stars

Faith helped out while we were gone for a long day and was a great communicator and also sent us photos of the fur babies! We plan to use her again for future needs!

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Emily S.
Drop-In Visits
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Book with peace of mind

  • 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?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • 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 Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet & Greet

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

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Greendale average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Greendale

Frequently asked questions about Rover

The average cost for Dog Sitting in Greendale on Rover is $17.76 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting 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 Sitting. For more information on service fees, click here .

As of July 2026, there are 2,368 sitters on Rover offering Dog Sitting across Greendale. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Greendale stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Greendale choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter 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 .

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.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Greendale with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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

  • 93% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% 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.

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 sitter.

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