Pet Sitting & Drop Ins In High Crossing

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated High Crossing pet 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: Amanda K.
Verified Background Check
Amanda K.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
184 reviews
59 repeat clients
20 years of experience
Cottage Grove, WI, 53527

Amanda went above and beyond to help me checking in to make sure my dog was okay. She picked up any mess they made while I was gone. She followed instructions and really seemed to care about my dogs and their well being. 10/10

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Katie T.
Sitter Profile Image: Chelsea B.
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Chelsea B.
from
$15
per visit
15 years of experience
High Crossing, Madison, WI, 53718

About: As a cat owner, I have a deep appreciation for cats and understand the patience, attentiveness, and consistency they need to feel comfortable and secure. I have cared for kittens, adults, and senior cats with a wide range of personalities and needs, which has given me hands-on experience with feeding routines, litter box maintenance, enrichment, administering basic medicine, and recognizing each cat’s individual personality and preferences. I know that every cat is different—some are playful and social, while others prefer quiet companionship and space—and I always take the time to build trust at their pace. My goal is to provide a calm, reliable presence that helps your cat feel safe, relaxed, and well cared for while you’re away. I work full-time during the day, but I am available after 4pm on weekdays and all day on weekends for your furry friend's needs. After giving lots of love to your fur baby, I go home to give lots of love to mine. I'm available for drop ins, short vacations. I take last-minute requests so long as my schedule allows it. I do not offer house sitting or boarding services at this time. Please contact me if you need drop in services for your cat or dog.

Sitter Profile Image: Kelsey T.
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Kelsey T.
from
$18
per visit
5.0 out of 5 stars
25 reviews
7 repeat clients
2 years of experience
Sun Prairie, WI, 53590

Kelsey too such great care of our pup! She checked in with me during her drop in visits, sent pictures and provided a summary of her activities with Shiner at the end of the day. She is extremely pleasant, responsive and responsible. I 100% recommend her to take care of your pets!

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James H.
Sitter Profile Image: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
278 reviews
62 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

I will have to book Jen again as my dog will sure miss her! She was wonderful and so easy to work with. Momo will definitely be sad she won’t see you as often. Thank you for all you do!

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Ash V.
Sitter Profile Image: Darby P.
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Darby P.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
28 reviews
8 repeat clients
15 years of experience
Rolling Meadows, Madison, WI, 53714

Darby is the best! She takes great care of our cats and considered things very thoroughly! We felt so relaxed and happy with the care and detailed communication Darby provided when we were on vacation.

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Bojie C.
Sitter Profile Image: Samantha S.
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Samantha S.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
47 reviews
18 repeat clients
25 years of experience
Madison, WI, 53704

Samantha has been so wonderful with my Australian Shepard. She gives amazing updates and always sends multiple picture updates! She is a great and compassionate sitter, Jonee and I appreciate her!

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Tiffanni S.
Sitter Profile Image: Hannah K.
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Hannah K.
from
$18
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
8 years of experience
Madison, WI, 53704

Thank you, Hannah, for watching my girls while I was out of town and playing with them and giving them infinite pets! I’m glad to know they were well taken care of!

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Sarah P.
Sitter Profile Image: Katelyn C.
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Katelyn C.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
39 reviews
13 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Thanks for taking good care of Eve for us during Christmas. She seemed to really enjoy your visits. We liked reading your friendly updates. Happy New Year, Katelyn!

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Robert V.
Sitter Profile Image: Adrianna C.
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Adrianna C.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
57 reviews
13 repeat clients
25 years of experience
Sun Prairie, WI, 53590

Adrianna took such good care of our kitty when we were away for the weekend. She administered his medication with no issue and made sure he was comfortable and loved on before she ended each visit. She updated us with lots of cute photos and detailed reports, too!

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Abbie B.
Sitter Profile Image: Blaze D.
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Blaze D.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Madison, WI, 53704

About: I’m all of my friends and families first choice to watch their pets when they are out of town. I’ve looked after a variety of breeds of dogs and many cats as well. I’ve always had dogs in my life growing up so I’m very familiar with reading their body language and knowing how to care for them. I work full time but have a lot of flexibility to check on your pet throughout the day and have the opportunity to work remote as well I’ve never a met a pet that didn’t like me. I’m very good at reading dogs body langue and knowing what they need. Cats also like me and I’m good at reading their body language as well

Sitter Profile Image: Rachael D.
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Rachael D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
24 reviews
8 repeat clients
10 years of experience
Sun Prairie, WI, 53590

About: I genuine care and give attention to every dog as if they were my own. I’m patient, reliable, and attentive to each dog’s individual needs. I’m comfortable working with puppies who are still learning routines, including basic training and potty schedules, and I’m also gentle and mindful with senior dogs who may need slower walks, medication reminders, or extra comfort. My goal is to make sure every dog feels safe, happy, and loved while their owner is away. I currently work only 2 days out of the week, but my schedule is very flexible, and can switch days if need be! Will accommodate I care for pets by making sure they stay comfortable and follow the routine they’re used to. In a client’s home, I provide feeding, fresh water, walks, playtime, and plenty of attention so pets feel safe while their owner is away. I also keep the home tidy and make sure pets stay on their normal schedule. If caring for pets in my home, I provide a safe, clean environment with supervised play, regular potty breaks, exercise, and lots of affection. I always pay close attention to each pet’s needs, personality, and any special instructions from the owner to make sure they feel happy and cared for.

Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
61 reviews
17 repeat clients
20 years of experience
Madison, WI, 53718

Jackie was absolutely fantastic! She took such good care of my boy, and was incredibly gracious and kind about adjusting the booking days when my travel plans changed. I was thrilled with her throughout the entire process, and incredibly grateful.

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Rachel C.
Sitter Profile Image: Megan H.
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Megan H.
from
$15
per visit
10 years of experience
High Crossing, Madison, WI, 53718

About: What sets me apart is my genuine love for animals. Spending time with pets is truly one of my favorite things, and I treat every pet as if they were my own. I enjoy getting to know each animal’s unique personality, whether that means playing with an energetic dog, giving extra attention to a cuddly cat, or providing gentle companionship to a senior pet. I believe pets thrive when they feel loved, comfortable, and understood, so I focus on building trust and creating a positive experience for them while you're away. Being around animals brings me so much joy, and I take pride in making sure they feel happy, safe, and cared for. You can count on me to provide plenty of affection, attention, and personalized care, along with regular updates so you can have peace of mind knowing your pet is in loving hands. I am currently a nursing student at UW Madison and have time throughout both the week and weekend to spend time with your pet! Typically earlier or later in the day is best for me but I am able to be flexible. I care for pets by sticking closely to their normal routine so they feel comfortable and at ease — feeding them on schedule, going on walks, playtime, and any specific instructions from their owner. I spend a lot of time giving attention and affection, whether that’s active play for energetic pets or calm companionship for seniors or more relaxed animals. I always try to make them feel safe and cared for while their owner is away. I also send updates so you know how they’re doing and can feel confident they’re in good hands.

Sitter Profile Image: Kathryn N.
Verified Enhanced Background Check
Kathryn N.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
36 reviews
12 repeat clients
10 years of experience
McClellan Park, Madison, WI, 53718

Kathryn did an amazing job caring for my grumpy old cat, Rumor. He doesn't usually like strangers, but she got him to play with toys and always spent time with him. I felt better knowing that she was checking in on him everyday!

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Katie A.
Sitter Profile Image: Jeff L.
Verified Enhanced Background Check
Jeff L.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
56 reviews
7 repeat clients
20 years of experience
Sun Prairie, WI, 53590

Jeff was wonderful to work with, and was great about accommodating a short notice booking. He left detailed updates about my dog, which definitely put me at ease. I will be booking with him in the future!

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Desiree D.
Sitter Profile Image: Hailey R.
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Hailey R.
from
$13
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
9 years of experience
Sun Prairie, WI, 53590

Hailey was very responsible and communicative. Would definitely have her help with Boots again!

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Michelle R.
Sitter Profile Image: Carley T.
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Carley T.
from
$19
per visit
5.0 out of 5 stars
6 reviews
4 repeat clients
20 years of experience
Westchester Gardens, Madison, WI, 53704

Carley is a delight and such a wonderful sitter! Incredibly sweet and a natural with animals, I had no worry at all leaving my pups in her care. Regular check-ins and photo updates throughout the weekend. I highly recommend Carley and will definitely try to book her again.

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Suzanne S.
Sitter Profile Image: Autumn H.
Verified Enhanced Background Check
Autumn H.
from
$18
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Autumn did such an amazing job with our cats. She took wonderful care of them and our apartment while we were gone. Thank you so much!

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Elizabeth A.
Sitter Profile Image: Megan T.
Verified Enhanced Background Check
Megan T.
from
$16
per visit
5.0 out of 5 stars
85 reviews
20 repeat clients
12 years of experience
Eken Park, Madison, WI, 53704

Megan was so fantastic with my energetic, young kitty!! She was very communicative and flexible. Will be using her services again. Thanks Megan!!

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Grace D.
Sitter Profile Image: Keezieng V.
Verified Enhanced Background Check
Keezieng V.
from
$19
per visit
5.0 out of 5 stars
68 reviews
30 repeat clients
3 years of experience
Carpenter-Ridgeway, Madison, WI, 53704

Keezieng is amazing! He’s available when I need someone to watch our dog in a pinch. He’s reliable and a big help when asked to do things that are above and beyond a drop in visit. We’re so thankful to have him as our Rover!

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Elizabeth M.
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High Crossing pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Anna is the best sitter we've ever had. She's amazing with our cats and keeps an eye on the house as well.

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

I love that Adrianna knows my cat's habits and behavior so well. She notices and lets me know if something is different, which I appreciate so much. She truly is an animal whisperer!

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Sue G.
Drop-In Visits
5.0 out of 5 stars

Adriana did a great job looking after my boy! I loved receiving the pictures and updates - I would recommend her to anyone in need of a cat sitter!

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

Claire took great and attentive care of our girls like she has every time she’s helped us for the past four years. I always feel reassured when I know she’s watching the cats when we’re away.

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Bennet G.
Drop-In Visits
5.0 out of 5 stars

Chelsea was kind enough to visit our cat on short notice. She did a great job visiting with Blue, sent us lots of photos, detailed updates, and our cat loved her!! We definitely recommend her :)

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

Jeff is amazing! He took great care of our cats while we were away for our wedding. His attention to detail and level of communication assured us that our little beans were in good hands with him. Both of our cats adored him and we will definitely be hiring him again!

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

Darby is such a lovely person who I trust to care for my babies while I’m away. Feels good to know they’re being checked on and loved.

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

Ollie was wonderful with our kitties! He is very communicative, kind, and does a thorough job making sure they’re okay/updating us <3 we appreciated that so much!

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

First time meeting Serenity and Tater and they appeared, from photos, comfortable and happy with Samantha. Being gone for two weeks, the photos of the various activities with my pups was very nice to have. Thank you for taking care of our pups!

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

Rosie loved Lynelle's visits, she was even flexible with some building access issues. Would highly recommend!

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

Lisa was great! Easy to work with, flexible, great with our cat Mobley, and prompt with her check ins and communication! 10/10 recommend Lisa

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Maya & George
Drop-In Visits
5.0 out of 5 stars

Carly took care of Chester for 1 week as drop-in sitter. My cat looks healthy and handsome as ever. I arrive with a chatty cat greeting me and I get it. I will book Carly again in the future because she not only took care of my cat’s needs (spoiled-prince) but she also respected my place and she is trustworthy and professional.

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Richard N.
Drop-In Visits
5.0 out of 5 stars

Alissa took excellent care of our two playful cats! She left great messages, took great pictures, and made sure our cats had plenty of attention and care while we were out of town. We would absolutely book her again.

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

Megan has been such a joy for our family! We have absolutely loved having her watch our dogs. They are obsessed with her, and she takes such great care of them. We are moving out of state and are so sad that we won’t get to work with her anymore. Thank you so much for everything, Megan!!

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Cat G.
Drop-In Visits
5.0 out of 5 stars

We had a one-time drop-in visit for our cat Noodle, and it was a great experience. Communication was prompt and clear, and they were right on time. Even though it was just one stop, they made sure Noodle was well taken care of and comfortable. We really appreciated the update and photos — it gave us peace of mind knowing Noodle was in good hands. You can tell they genuinely care about animals and take their responsibility seriously. Reliable, kind, and professional. We would absolutely book again and highly recommend

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Mitch
Drop-In Visits
5.0 out of 5 stars

We are very pleased to have connected with Olivia. She is responsible, and very easy to work with, and communication has been excellent.

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

Sylvia was consistent and prompt with her visits and updates of our two cats. She was attentive and accommodating to our needs for a date change, plant watering, and trash pickup. We’ll certainly rebook her.

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Michael C.
Drop-In Visits
5.0 out of 5 stars

As my first experience using Rover, I am very thankful to have found Cassandra!! We hired her for drop in visits, and she left us with daily reports and many happy kitty pictures. :)) I could tell our cat was enjoying her company very much. We’re so grateful to her for watching him on short notice over the holiday, and for her professionalism. She is a great communicator, and very responsive in her messages. I couldn’t have asked for a better person to look after our little guy. :)) Thank you!!!

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

Nick did an excellent job taking care of Mochi. His litter box was cleaned and his feeder and water fountain were maintained when I returned.

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Jamie G.
Drop-In Visits
5.0 out of 5 stars

Autumn was wonderful for our cats. They were well taken care of and it was as though we weren’t gone!

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Tara L.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a High Crossing pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

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

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in High Crossing.

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

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

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

Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.