Dog Sitting in Cross Plains

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

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Top rated Cross Plains dog sitters

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: Ann A.
Verified Enhanced Background Check
Ann A.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
120 reviews
42 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: Anna N.
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Anna N.
from
$13
per visit
20 years of experience
Middleton, WI, 53562

About: I have always had a cat and a large dog as a kid. I trained my childhood dog when I was 10 to behave and walk well. Now I have 2 cats, a little tabby and a big Siberian boy. I love dogs but just don't have the space for one in my apartment currently. For as long as I can remember, I’ve been the first call from my friends who need a dog or cat sitter! I am currently doing school for the summer and I am looking for things to do with my afternoons and evenings! Im really flexible between the hours of 2pm-midnight! I am happy to do anything needed of me! From feeding to cleaning the litter box to fetch and playtime, even giving medicine! I’m willing to do anything needed!

Sitter Profile Image: Xiyuan D.
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Xiyuan D.
from
$18
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: 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

Great communication, wonderful care of our 2 cats while we were out of town. Sidney even picked up some extra food because I had miscounted the number of cans we needed. Thanks so much!

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Ronni H.
Sitter Profile Image: Isaak B.
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Isaak B.
from
$13
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Mapleton-Flatlands, Middleton, WI, 53562

About: I’ve had dogs and cats my entire life! From chihuahuas to border collies, I’ve had experience raising and taking care of all sizes of animal. I have a pretty open availability, so I would be able to give your animals the utmost attention when needed! Weekends are just as good for me as the weekdays! Having had animals my whole life, I understand how to maintain a clean environment while working with them. I am perfectly fine and comfortable with cleaning up after your animals if need be.

Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$16
per visit
5.0 out of 5 stars
1 review
5 years of experience
Madison, WI, 53719

About: I’m a lifelong animal lover, experienced pet owner, and former veterinary assistant who cares for both dogs and cats. I understand how important it is to find someone trustworthy, attentive, and patient with your pets. I’m comfortable with walks, feeding routines, playtime, cleanup, and providing lots of love and attention while you’re away! 🐾 I work full-time during weekdays, so my availability is mainly evenings and weekends. I’m fully available on weekends for walks, drop-ins, and extended care, and I’m happy to help provide reliable, loving care around my work schedule. Your pet’s safety and comfort are always my top priorities. As a former veterinary clinic assistant and experienced pet owner, I pay close attention to routines, behavior, and any special care instructions to help your pets feel safe and stress-free. I’m attentive, reliable, and committed to providing a calm, loving environment.

Sitter Profile Image: Megan R.
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Megan R.
from
$24
per visit
5.0 out of 5 stars
17 reviews
8 repeat clients
10 years of experience
Blackhawk, Madison, WI, 53717

Megan took great care of our dog while we were gone for the week. She was prompt, gave updates with each visit, and sent pictures. We highly recommend Megan!

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Julie S.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$18
per visit
10 years of experience
Verona, WI, 53593

About: I have had dogs since my childhood and have worked with breeds of different sizes and backgrounds, including some with special needs. In my home life, I have two cats that I adore and spend much of my free time with. I’m available all day on weekends, as well as from 5:30pm onward on weekdays (typically). If you have specific requirements for your animal let me know and we can create a schedule that works best for you! I can perform any specific needs that your pet may need. One of my own pets has special medical requirements, so I am familiar with taking care of animals that need extra care.

Sitter Profile Image: Julia G.
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Julia G.
from
$15
per visit
5.0 out of 5 stars
8 reviews
3 years of experience
Middleton, WI, 53562

Julia was an absolute godsend for us. My dog had quite a few issues while we were out of town, and Julia was amazing. She gave me constant updates, came to check on him regularly outside of what was originally booked, and made sure that my dog was safe and cared for. She helped ease my worries, and I would definitely rebook her, no questions asked. Our cat also loved hanging out with her!

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Galilea B.
Sitter Profile Image: Kathryn P.
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Kathryn P.
from
$18
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
11 years of experience
Sauk Creek, Madison, WI, 53717

No notes! Was reunited with my lil guy and he looks great. Loved getting pics and updates while I was gone.

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Abby P.
Sitter Profile Image: Evelin C.
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Evelin C.
from
$24
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
3 years of experience
Verona, WI, 53593

About: I’ve always been a dog lover, growing up with a Pitbull Terrier, and I've had experience taking care of dogs of all sizes. Over the years, I’ve helped out friends and family with everything from puppy care to looking after older dogs, whether it’s at my place or theirs. I’m comfortable with both big and small dogs, and I’m happy to provide whatever your pet needs—whether it’s walks, playtime, feeding, or just some extra attention. I treat every dog like they’re my own, making sure they feel safe, loved, and well cared. I do have a dog of my own, Dewey. He’s a very sweet boy and loves meeting and playing with new friends of all sizes and ages. He’s a good listener, so he knows how to respect other’s boundaries. I do have a full-time job but am available most weekends. I do have some flexibility during weekdays when I work from home, so I will always try my best to work with your schedule. My current routine with Dewey is 3-4 walks, including at least 30 minutes of playtime at the fenced play area or a long walk. Dewey makes great company for your pup and does not mind sharing his toys. He loves being outdoors and free, so I try to give him as much playtime as possible, and will do the same with yours. A tired pup is a happy one!

Sitter Profile Image: Autumn P.
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Autumn P.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Middleton, WI, 53597

About: I love all animals but have a soft spot for older dogs and cats that might need a little extra love and attention. I grew up with dogs but currently have a 5 year old calico cat named Coco. I am a teacher who has much more free time in the summers. I am looking for afternoon/evening weekday jobs for this summer! I love walking. I will come to your home and make your fur baby feel comfortable in their own space. I can also take them for walks and/or play with them in your home. I can also bring animals to my apartment for animals that need more attention and care.

Sitter Profile Image: Evan T.
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Evan T.
from
$13
per visit
5.0 out of 5 stars
11 reviews
2 repeat clients
6 years of experience
Middleton, WI, 53562

Evan did a great job with my two cats. Everything went smoothly, he arrived consistently at the same time. I enjoyed the photos of my cats and the updates on how they were doing. They definitely seemed to like him. Would book again!

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Emily S.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$15
per visit
5.0 out of 5 stars
5 reviews
25 years of experience
Maple-Prairie, Madison, WI, 53719

About: Animals have always been a big part of my life! I grew up with dogs, which taught me the importance of routine, exercise, and lots of love. Now I’m a proud cat owner of two, so I also understand how to care for more independent (but equally lovable!) pets. Whether your pet loves to play or just needs a calm, reassuring presence, I’m happy to meet them where they are and make sure they feel at home. I work full time at UW Madison during regular business hours between 7:30a and 4:30p. I have a flexible schedule where I work from home twice weekly and at work 3 days. I care for your pets and your home as if it were my own. I treat the pets with the upmost love and care, and respect your home and privacy. I play with the pets if they are interested, and leave them be if not interested. Pets have bodily autonomy and I respect that. I’ll clean up a mess if I find one, and I’d let you know immediately if there’s an issue.

Sitter Profile Image: Hailey M.
Verified Enhanced Background Check
Hailey M.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
10 years of experience
Madison, WI, 53704

Hailey was amazing with my two cats! From the photos she shared, I could tell that they were completely happy and comfortable with her. She sent detailed reports and lots of photos, which gave me peace of mind that the kitties were doing well while I was away. Thank you, Hailey!

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Erma D.
Sitter Profile Image: Mackenzie B.
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Mackenzie B.
from
$13
per visit
3 years of experience
Madison, WI, 53717

About: I have experience pet sitting for dozens of families across several states and am passionate about caring for others beloved pets. I am trustworthy, communicative, and responsible and will meet your pets needs to perfection. I am currently working full time as a social worker but am able to before and after work and have a lot of flexibility on weekends. I appreciate being able to speak with you prior to beginning services so I can get to know your pet and their specific needs. I ensure that clients pets and my own pets have a safe home with consistency. I know each pet has their own needs or preferences and enjoy molding my work with them to meet those requirements.

Sitter Profile Image: Nicole Z.
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Nicole Z.
from
$25
per visit
5.0 out of 5 stars
12 reviews
1 repeat client
8 years of experience
Middleton, WI, 53562

About: Although I’m new to Rover, I bring several years of pet care experience for friends and family, both in-home and in my own. Since I don’t currently have a pet, I look forward to giving yours my full attention and care. I’m comfortable with both dogs and cats of all sizes and love giving them plenty of walks, playtime, and snuggles. With a flexible remote work schedule, I can provide consistent care during the day, evenings, and overnights. As an early riser, I enjoy starting mornings with a walk, and I make sure your pet receives lots of attention, exercise, and companionship any time of day. I provide loving care while making sure your pet’s routines are followed exactly as directed, from feeding schedules to walks and playtime, so they stay comfortable and safe. I’ll also share regular updates and photos, giving you peace of mind while you’re away.

Sitter Profile Image: Skyler B.
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Skyler B.
from
$20
per visit
15 years of experience
Cross Plains, WI, 53528

About: I grew up with five dogs. I worked at a dog daycare for the past 6 months. While I worked there, I gave them enrichment, affection, cleaned up poop from the yards, and supervised dogs to make sure they played safely. I am free any time on the weekends. I will be getting a new job so I'm not 100% sure what my weekday hours are going to be like as of right now. I will be taking care of clients' pets in their own home or yard because we live in an apartment and also have three cats.

Sitter Profile Image: Jolie Zevallos
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Jolie Zevallos
from
$17
per visit
5.0 out of 5 stars
19 reviews
6 repeat clients
8 years of experience
Madison, WI, 53715

Jolie was great with my three dogs. They clearly enjoyed her visits with her and she sent me lots of pictures. Followed all the notes I left and I felt very confident and comfortable with her caring for my pack.

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Hope R.
Sitter Profile Image: Alex P.
Verified Enhanced Background Check
Alex P.
from
$25
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
17 years of experience
Cross Plains, WI, 53528

About: I grew up around pets and always loved them. All through undergrad and graduate school, I have been a pet sitter and house sitter. Once I was done and could finally get a pet of my own, I got one frenchie… and the other followed just a few short months later. My puppies are my whole world, and they LOVE having new friends! I work full-time from home, and have a fenced backyard! Our house gets lots of natural light which means sunny naps indoors when it’s chilly. I take our pups on at least one long walk a day, and plenty of playtime inside and outside. I have a fenced yard and lots of open space in the home. My two Frenchies LOVE all dogs - for playing and snuggling during the day. I love hanging out on the couch with our pups and relaxing, going for nice walks when weather permits, and lots of play with toys and balls!

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Over 15
pet parents in Cross Plains have booked dog sitting

Cross Plains dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Peyton has cared for our dogs on two separate occasions, and we have been extremely happy with her services both times. She is punctual, reliable, and clearly has a genuine love for animals. We really appreciate the care and attention she gives our dogs, and it’s reassuring to know they’re in such good hands when we’re away. Peyton provides excellent communication and always follows through on what she says she’ll do. We highly recommend her to anyone looking for a trustworthy and dependable pet sitter!

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

Peyton did an amazing job caring for Charlie & Lloyd while we were away. She stopped by our home twice, took them out, fed them, and spent time playing with them. We felt completely at ease knowing they were in such good hands. We’re very happy with her service and highly recommend her.

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allison S.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog sitting in Cross Plains is $20

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Sitters in Cross Plains average 6
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Cross Plains on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Cross Plains dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,442 dog sitters in Cross Plains. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Cross Plains dog sitters respond in under an hour.

Dog sitters in Cross Plains have an average of 16 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Cross Plains.

Rover makes it easy to find Cross Plains dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 1,442 dog sitters in Cross Plains on Rover, so you’re sure to find the perfect match for your dog! In Cross Plains, 94% of dog sitters offer daily exercise, 96% offer medication administration, and 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.