Pet Sitting & Drop Ins In Westchester Gardens

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 Westchester Gardens 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: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
275 reviews
62 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

Jen was amazing! We loved getting daily updates and pictures. We could always tell from the photos that our boys were having the time of their lives. Can't wait to have Jen back again!

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Beth H.
Sitter Profile Image: Samantha S.
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Samantha S.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
46 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: Carley T.
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Carley T.
from
$19
per visit
5.0 out of 5 stars
6 reviews
3 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: Darby P.
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Darby P.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
27 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: Keezieng V.
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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's assistance was a lifesaver this holiday season. His politeness and kindness when meeting us and our cat Olivia was reassuring and he did a great job of updating us during his visits while we were away. We’re so grateful for the excellent care provided!

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Elizabeth M.
Sitter Profile Image: Autumn H.
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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

Great communication!

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Stuart H.
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: 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: Hailey M.
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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 did amazing the pups were happy and we were happy. We only cut our trip short because I got sick but we will definitely be using her again. Thank you Hailey for taking care of Luna and Kane.

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Kelly R.
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: Megan T.
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Megan T.
from
$16
per visit
5.0 out of 5 stars
84 reviews
20 repeat clients
12 years of experience
Eken Park, Madison, WI, 53704

Megan is awesome!! Megan was able to help us with feeding and checking in on our cats. Our cats have different foods/needs and Megan handled it all well! Definitely will use for pet sitting again!!

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Jess B.
Sitter Profile Image: Alexandria P.
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Alexandria P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
16 years of experience
Madison, WI, 53704

Alexandria was amazing she went above and beyond for our family while out of town. My dog Indy looks forward to her visits and she took care of my hens too. Amazing.

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Mahala D.
Sitter Profile Image: Brook P.
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Brook P.
from
$15
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
20 years of experience
Madison, WI, 53704

About: What sets me apart as a pet sitter is the lifelong experience and genuine love I have for animals. I grew up in a home full of dogs and have always been surrounded by pets, learning early on how to care for them with patience and attention. Today, I have a dog and a cat of my own, so I understand how important it is to find someone you can trust to care for your furry family members. I treat every pet like my own, with kindness, consistency, and a lot of love. Whether it's a walk, a drop-in visit, or just some extra playtime, I ensure your pets feel safe, happy, and well cared for while you're away. As a teacher on summer break, I have a very open and flexible schedule, which means I’m available throughout the day to give your pets the attention and care they need. Whether it’s a morning walk, midday playtime, or an afternoon check-in, I’m able to provide consistent, dependable care. My background in teaching also means I’m organized, responsible, and great at following routines—qualities that translate well into attentive, loving pet care. When caring for pets in a client’s home, I prioritize maintaining their routine to help them feel safe and comfortable. I follow feeding schedules, provide fresh water, give walks or playtime, and make sure they get plenty of love and attention. I’m respectful of your home and any instructions you leave, whether it’s about medications, crate time, or favorite toys. If I were to offer care in my home, pets would have a calm, pet-friendly space and lots of companionship throughout the day. No matter the setting, I treat every pet as if they were my own, making sure they feel happy, secure, and loved while you're away.

Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
42 reviews
13 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Liz was very flexible and willing to help with my 3 pit bull/bully doggies on short notice. Very kind and understanding. Great help. Thanks Liz!

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Julia X.
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
16 repeat clients
20 years of experience
Madison, WI, 53718

Jackie and her family took wonderful care of our dog. Jackie was very accommodating to my care request and was communicative the entire time. I would absolutely recommend Jackie and her family!

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Becca S.
Sitter Profile Image: Ben K.
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Ben K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
117 reviews
24 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

Ben provided excellent care for our dog and cat while we were on vacation for a week! He did 3 drop-in visits a day, arrived on time, and provided pics and videos. THEN, when our flight was delayed and we were stuck for two additional days, he covered those visits as well, which was amazing as we were already under a ton of stress due to the delay. We will definitely book Ben again and highly recommend.

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Sara P.
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: Cassandra B.
Verified Enhanced Background Check
Cassandra B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Madison, WI, 53704

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.
Sitter Profile Image: Ansheera H.
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Ansheera H.
from
$15
per visit
5.0 out of 5 stars
1 review
10 years of experience
Rolling Meadows, Madison, WI, 53714

About: I’ve shared my life with animals for over a decade, and my heart truly belongs to dogs and cats. As a homeowner and a "dad" to three pets of my own, I understand that your animals aren't just pets—they’re family. Why Choose Me? -I’ve been with my own buddies for 10 years, navigating everything from post-op surgery care and complex medication schedules to senior "attitudes" and puppy smiles. -I am a hybrid worker with a flexible schedule and my own transportation, making it easy for me to drop in for walks or midday snuggles. - I treat every home with the same care I give my own. You can expect a clean space and frequent, proactive communication so you never have to wonder how things are going. -Whether your pet has a specific routine or a quirky habit, I follow instructions to the letter to ensure their comfort remains consistent. I know the peace of mind that comes with knowing your fur babies are happy, safe, and loved while you’re away. I’m here to provide that same comfort for you. Work mostly from home with one day in the office. Very flexible on needs and schedule! Up early and go to bed late, which makes my schedule open to accommodate the needs of our little fur friends. I respect your space, privacy, and needs to ensure your home is just the way you left it when you return. In my home, we keep a clean ship, organized, and make sure all fir buddies are rewarded with treats when good behaviors are exhibited. With instruction, can be mindful of any special needs for our fur friends. Their health and comfort matters too!

Sitter Profile Image: Della H.
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Della H.
from
$15
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Windsor, WI, 53598

Della did a fantastic job of taking care of our cat, spending time with him and looking after his needs. She was reliable and a great communicator.

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Virginia F.
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Westchester Gardens pet parents share their Rover experiences

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5.0 out of 5 stars

Baylee was AMAZING! She was flexible with the times she was able to stop over, carefully watched the weather and opened and closed the windows so the cats could stay entertained while we were gone but the house didn’t get wet 🙃 our shy cat even came out to see her every time she stopped over! She kept us up to date with pictures and information with each visit. Would definitely use her again

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

Brittany was so amazing with our Kitties! She is kind and was attentive to some special Instructions we have for our babies. 10/10 would hire again!

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Alec C.
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

Alexandria has watched our two cats twice now and has been a great, reliable sitter. She communicates well, sends lots of pictures, and provides helpful updates. I'll continue to use her in the future!

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

Jen was so loved by my pups! She did a great job being a friendly stranger for my two dogs. She included numerous photos and told me how the drop in went during each visit. I plan on hiring her again when my other rovers are unavailable! Thank you so much!

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

Kristina did a great job watching our cats (and fish), despite the myriad health conditions among the 3 of them. They were all well-cared for and everything was tidy when we came home.

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

Katherine is awesome! She sent lots of pictures of our kitty while we were away and let us know how he was doing. Would 100% recommend!

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Mikayla V.
Drop-In Visits
5.0 out of 5 stars

Elizabeth did a great job taking care of our cats. They seemed very happy under her care and we got some very cute pictures !

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

It was a pleasure meeting with Christine and having her watch our cat, Kuzya. It was easy to communicate with her and arrange everything. She understood how to connect with Kuzya and sent us great pictures and updates. We will definitely contact her again when we need a cat sitter!

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Masha T.
Drop-In Visits
5.0 out of 5 stars

Megan is always the best with my girl!! She sends so many good pictures and report cards from her visits. I always feel safe and confident having her come over.

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Anna S.
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

Lily is our go-to pet sitter and she always takes the best care of our cat Henny and sends the sweetest photos of him! She's also extremely reliable, friendly and always on time. Could not recommend her enough!

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Kate D.
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

Anna is great! Her daily summaries are some of the best in the business, and it shows just how much she lives your furry best friend. We will definitely be continuing to have Anna come over when we need some extra help!

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

I knew Alyssa was going to be the perfect pet sitter for my two kitties when I first met her and she was super cuddly with my little gray boy. But when she sent not only photos but a video which featured my very nervous, very reclusive gray tuxedo girl my first impressions were confirmed! Alyssa was wonderful. I trusted her with my precious buddies and in my home and will definitely trust her in the future!

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Susan J.
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

Joan provided absolutely fantastic care for our senior cat! She gave lots of updates and clearly made the extra effort to make Gus feel cared for while we were away. She is extremely communicative. Thank you Joan!

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Genevieve C.
Drop-In Visits
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Frequently asked questions about Rover

If you’re searching for a Westchester Gardens 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 Westchester Gardens.

Rover makes it easy to find Westchester Gardens 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.