Dog Sitting Middleton

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

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Over 495
pet parents in Middleton have booked dog sitting

Middleton, 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.

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Sitter Profile Image: Julia M.
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Julia M.
from
$18
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
University Apartments, Madison, WI, 53705

About: Hi! I’m a graduate student who loves animals and understands how important it is to find someone you trust to care for them. I have experience caring for dogs with different temperaments, including dogs with anxiety and dogs who need medication or extra patience. I’m very responsible, detail oriented, and I take pet care seriously - I know I’m caring for a member of your family. I’m happy to follow your pet’s normal routine as closely as possible, including walks, feeding schedules, crate routines, and any specific instructions you have. I’ll also send regular updates and photos so you know your pet is doing well. My schedule is flexible, and I’m available for drop in visits, walks, and house sitting. I’m reliable and will always communicate clearly about timing and availability. Your pet’s safety and comfort comes first. I follow routines, use secure leashes, provide updates, and create a calm, safe, consistent environment for your pet

Sitter Profile Image: Sophia D.
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Sophia D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
14 reviews
8 repeat clients
10 years of experience
Madison, WI, 53705

Sophia is a very caring and responsible person. I would highly recommend Sophia for your pet.

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Sharmin I.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
30 years of experience
Regent, Madison, WI, 53726

Amy did such an amazing job! Even my shy cat came out for photos. She took extra care to ensure she was playing with them, which felt great as some people assume “they are just cats” and don’t need that extra interaction. Her updates were thorough, and I’m definitely getting some of the pictures she took of them framed!! After an especially scarring experience with a prior sitter, it feels nice to be able to trust someone again. Will definitely be using her again

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Ashley A.
Sitter Profile Image: Molly H.
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Molly H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
15 reviews
5 repeat clients
25 years of experience
Middleton, WI, 53562

Great experience. Our 2 dogs received wonderful care. To learn the routine, Molly spent a lot of time with us prior to her first day taking care of Truman and Nemo. Highly recommended

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Mike L.
Sitter Profile Image: Iva & Eduardo P.
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Iva & Eduardo P.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
19 reviews
8 repeat clients
22 years of experience
Verona, WI, 53593

Iva and Eduardo are amazing! Danny had so much fun on their visit. They were very very communicative and share plenty of pics and updates. Danny is a bit rowdy and they had no issues handling him. I would highly recommend them to anyone. :)

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Celina S.
Sitter Profile Image: Mandi W.
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Mandi W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
7 years of experience
Verona, WI, 53593

Fantastic coverage for my 2-week absence. Mandi even got my formerly-feral cat comfortable enough to come out and sit in the hallway during her visits, which is an accomplishment for a stranger! She takes detailed notes and asks all the questions during the meet & greet, and had a great idea for key return under the door.

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Beth S.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
132 reviews
49 repeat clients
10 years of experience
Madison, WI, 53719

Ann is SO kind and sweet and was extra patient with our fearful rescue dog! She provided great communication and updates and it is clear she cares a lot about pets. We really appreciated her being able to check in on Pumpkin on Thanksgiving night and would absolutely reach out to her again.

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Claire B.
Sitter Profile Image: Erin C.
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Erin C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
14 years of experience
Middleton, WI, 53562

Erin was absolutely wonderful! I was nervous about how my dog would do since she is a pretty anxious girl and is used to having me home with her all the time. But Erin took the time to get to know her and she warmed up to Erin right away. It was obvious from the pictures during the check-in that Finley was calm and enjoying the play (and some snuggles). It was such a load off my mind knowing she was well cared for while I had to be away. Erin is such an animal lover and they can sense her kind soul! Thank you!!

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Emily A.
Sitter Profile Image: Elena "Sofi" R.
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Elena "Sofi" R.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
44 reviews
12 repeat clients
5 years of experience
Capitol, Madison, WI, 53715

Sofi was patient and caring for my dog. My dog warmed up to Sofi more and more each drop in visit. She was great at communicating and sent adorable pictures. Very reliable!

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Ashley Paige R.
Sitter Profile Image: Skylar S.
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Skylar S.
from
$15
per visit
5.0 out of 5 stars
5 reviews
13 years of experience
Verona, WI, 53593

About: I have been taking care of all types of animals since I was a teenager. I am great with dogs both large and small. My friends also call me the cat whisperer because I can earn any type of cats trust. I work Monday-Friday and get done around 4pm. I am very open on the weekends and every night of the week. Additionally my work schedule is flexible so if you need specific accommodations I can most likely make that work. I have a pet friendly apartment with lots of grass to run around in to play and go to the bathroom. Additionally my apartment is a comfy and cozy home with nothing that animals would be getting into.

Sitter Profile Image: Khushi R.
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Khushi R.
from
$14
per visit
4 years of experience
Middleton, WI, 60074

About: I have been working with dogs for over 4 years, including basic training, walking, brushing, and giving them love! I have worked in shelters with dogs of all ages and sizes, and would be honored to be trusted with your loved little one. I am currently part time, so I would love to attend to your pet after my schedule. I can do drop-ins and check ups in the evenings for the weekdays and my schedule would be more available for the weekend. I would love to check-in with your furry friend at your home. I am comfortable with free-roam or crating your pet, as well as walking, allowing yard time, feeding etc.

Sitter Profile Image: Austin C.
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Austin C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
85 reviews
31 repeat clients
5 years of experience
Madison, WI, 53719

Austin is a dream walker! I got about 20 adorable pictures a day, all wallpaper and insta worthy ? He looked after my boisterous boy with enthusiasm, care and diligence. I cannot wait to plan my next vacation only so that newton and Austin can have more time together! ❤️ thank you so much, Austin!

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Nikita K.
Sitter Profile Image: Sidney R.
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Sidney R.
from
$20
per visit
5.0 out of 5 stars
84 reviews
33 repeat clients
20 years of experience
Middleton, WI, 53562

Sidney was on time, easy to communicate with, and took exceptional care of our cat! We were able to find a schedule that worked for both parties, and we received photo and text updates for each visit. Sidney is our new favorite pet sitter in the area!

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Ethan & Allison M.
Sitter Profile Image: Meeka M.
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Meeka M.
from
$23
per visit
5.0 out of 5 stars
85 reviews
23 repeat clients
10 years of experience
Madison, WI, 53717

Another great experience with Meeka! I have no worries when she kitty sits! And the cats obviously love her cuz they’re so calm when I return!

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Lisa R.
Sitter Profile Image: Xiyuan D.
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Xiyuan D.
from
$20
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
4 years of experience
Middleton, WI, 53562

Super responsive!

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Olivia B.
Sitter Profile Image: Jess B.
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Jess B.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
57 reviews
17 repeat clients
10 years of experience
Madison, WI, 53719

I had the best vacation knowing my fur babies were in great hands . Jess was amazing with them . I couldn’t ask for a better sitter . She’s great ! I will hire her again and again !!

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Angela F.
Sitter Profile Image: Eric &  Rachel D.
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Eric & Rachel D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
24 reviews
7 repeat clients
9 years of experience
Capitol, Madison, WI, 53703

About: Eric and Rachel share a love for their beloved Aussie-beagle Lilo and fostering rescue dogs together. We know that it is never easy to leave your beloved dog with someone new, and in a new place. As our own Lilo has struggled with separation anxiety before, we know how important it is to have a pet sitter who is present, patient, and able to cater their care towards a dog’s specific needs. Rachel has taken care of 6 different family dogs growing up, including a border collie, golden retriever, Boston terrier, 2 mixed breeds and a silky terrier. Eric has taken care of his family dog (chihuahua mix) since birth till now (11 years old). Together, we have fostered 16 rescue dogs these past two years, ranging from a high energy Great Pyrenees to 3 Border Collie puppies all at once, to a completely afraid and anxious Beagle mama and Shiba Inu mama that are recovering from very difficult situations. We have also looked after American pit bulls, a large Newfoundland, and senior doggies who have hip difficulties and special diets. Our own dog is a 3.5 year old Aussie-beagle, so we particularly love the herding dogs. :) We both have lots of experience working with dogs of all kinds of temperaments and needs, especially high energy dogs who require a lot of attention and care, and administering medication to dogs who have special needs. Rachel also loves cooking her home cooked meals for her dog, and can do that for yours too, if you need! We both work from home and have all weekends free. Our flexible schedules together allows us to bring dogs regularly on walks and to look after them consistently. We follow instructions really well, and can take care of your dog according to your requirements. We allow dogs to roam and sleep freely in our home, but we can also crate your dog easily if you prefer. We know how to work with your dog with lots of gentle care and love.

Sitter Profile Image: Jennifer G.
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Jennifer G.
from
$25
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Middleton, WI, 53562

The sweetest human ever took great care of my dogs. I would definitely use Jennifer again. She’s the best.

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Kimberly M.
Sitter Profile Image: Gen A.
Verified Background Check
Gen A.
from
$30
per visit
5.0 out of 5 stars
333 reviews
201 repeat clients
7 years of experience
Middleton, WI, 53562

Gen is amazing! She watched my troublemaking cat all week and went above and beyond to try to fix his water fountain that he broke! If I ever need anyone watching Artie again Gen will be my first choice.

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Brooke J.
Sitter Profile Image: Megan B.
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Megan B.
from
$20
per visit
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

About: I’ve been caring for my own cats since I was in 3rd grade, learning the importance of caring for them in many aspects through feeding them, cleaning their litter boxes, and respecting their needs of play time vs needing space. I started caring for my friends animals in college and that’s when I learned more about dogs and how to tell what dogs are friendly, when they need space, etc. Respecting animals and giving them the love and care they deserve is of utmost importance to me. I have a fairly flexible job, so I’m able to fit in visits almost any time of day. The only day I’m not flexible is Sunday, I work a mandatory 12 hour, so could stop in after my shift but not before or during. Respecting people’s space and privacy is important to me, if I’m walking your dog and caring for your cats, you can trust me to do the job at hand and leave your space in one piece. Keeping a clean home is important to me, so you can rest assured that if your pet makes a little mess, it will be cleaned up for you and you’ll never know it happened.

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The median cost per visit for dog sitting in Middleton is $20

Dog parents share their Rover experiences - Middleton

1 / 1
5.0 out of 5 stars

Molly was great! So thoughtful and attentive to our Lucy. I especially appreciated her informative updates. We came home to a happy well cared for dog.

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Julie J.
Drop-In Visits
5.0 out of 5 stars

Jennifer went above and beyond to take care of my best friend. He fell in love with her and was always excited to see her. Jennifer gets 100 stars from me! I highly recommend her!

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Pam S.
Drop-In Visits
5.0 out of 5 stars

Jennifer was great! She made sure to come by the day before to get familiar with my set up and meet my girls. I definitely recommend her to anyone new to Rover.

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Lisa H.
Drop-In Visits
5.0 out of 5 stars

Excellent and prompt care! We felt really comfortable leaving our pup at home knowing Stefanie was checking on her!

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Baylen W.
Drop-In Visits
5.0 out of 5 stars

Hannah was fantastic with our dog Cooper! She was reliable, responsive, and took excellent care of him. We came home to a happy pup and had complete peace of mind while we were away. Highly recommend!

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Courtney S.
Drop-In Visits
5.0 out of 5 stars

Alliyah has been so wonderful! She has stopping by to care for my dog during my long work days. My dog loves her! Highly recommend!

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Alysse L.
Drop-In Visits
5.0 out of 5 stars

Sabrina was the absolute best and took amazing care of our two large unruly huskies and two cats. Your furry family members will be in great hands with Sabrina. Super timely, professional, and wonderful personality. Thank you for everything Sabrina. Wish I could give more than just 5 stars. =]

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Nood
Drop-In Visits
5.0 out of 5 stars

Natalie was available on relatively short notice and made us feel totally comfortable that our dog was in good hands while we were away.

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Tim H.
Drop-In Visits
5.0 out of 5 stars

Lydia is awesome! We were super worried about leaving our dog but both times we have booked Lydia, our dog didn’t even bark when we left.

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

Such a well dog sitter! Came to meet my dog and asked a lot of good questions on how to provide and care for my dog! She came did her thing just like how I told her and she went beyond! Gave me a lot of photos during the care and a lot of note taking on how my dog was! Definitely will book again and recommend her!

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Choua Y.
Drop-In Visits
5.0 out of 5 stars

Amazing, she went out of her way to pick my dog up and take him home for me when I was out of state.

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J F.
Drop-In Visits
5.0 out of 5 stars

Ryan arrived on time and did a drop in visit with our pup as expected. He has a professional demeanor and seems genuinely to enjoy spending time with our pet.

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Tim S.
Drop-In Visits
5.0 out of 5 stars

Erin was absolutely wonderful! I was nervous about how my dog would do since she is a pretty anxious girl and is used to having me home with her all the time. But Erin took the time to get to know her and she warmed up to Erin right away. It was obvious from the pictures during the check-in that Finley was calm and enjoying the play (and some snuggles). It was such a load off my mind knowing she was well cared for while I had to be away. Erin is such an animal lover and they can sense her kind soul! Thank you!!

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

Hannah does a fantastic job taking care of my dogs when I travel. It’s a huge load off knowing someone responsible is watching them

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

Meaghan was awesome with our puppy! Kept us updated and sent pictures throughout her time with our pup! Super reliable and quick to answer! :)

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Maddie T.
Drop-In Visits
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Popular requests for dog sitting - Middleton

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Sitters in Middleton average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Middleton

Frequently asked questions about Rover

The average cost for Dog Sitting in Middleton on Rover is $22.2 per visit (as of August 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 August 2026, there are 1,388 sitters on Rover offering Dog Sitting across Middleton. 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 Middleton 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 Middleton 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 Middleton 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 Middleton. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 94% 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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