Pet Sitting & Drop Ins In Williamsburg

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 Williamsburg 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: Ilene G.
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Ilene G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
7 years of experience
Riverwest, Milwaukee, WI, 53212

Ilene was a great sitter for our two-year-old kitty! She was very communicative, flexible and laid-back. She was able to come for a meet-and-greet ahead of time and amended the drop-in time, per my request, partway through our trip. We really appreciated her detailed write-ups and quality photos. Thank you, Ilene!

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Annamarie H.
Sitter Profile Image: Katie S.
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Katie S.
from
$15
per visit
5.0 out of 5 stars
16 reviews
3 repeat clients
11 years of experience
Cambridge Heights, Milwaukee, WI, 53211

Katie consistently goes above and beyond. Our cat was alone during a snowstorm and power outage, and Katie communicated with us right away that our automatic feeder wasn’t working. She worked with me to come up with a mitigation plan, and she offered to check on our cat the next day to make sure the kibble had dropped, even though we hadn’t booked her for another visit. She is an AMAZING sitter and very kind, generous human.

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Annamarie H.
Sitter Profile Image: Angela M.
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Angela M.
from
$18
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Whitefish Bay, WI, 53217

Angela was great. The animals loved her and she left good descriptions and pictures with every visit.

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Aidan F.
Sitter Profile Image: Travis H.
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Travis H.
from
$25
per visit
5.0 out of 5 stars
337 reviews
104 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis was wonderful and highly recommend! We kind of booked last minute and he was so accommodating doing a meet and greet before dropping in on our boys. Our boys loved him and we will definitely be using him for future services!

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Brandon Y.
Sitter Profile Image: Maggie S.
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Maggie S.
from
$16
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
10 years of experience
Riverwest, Milwaukee, WI, 53212

About: One of my favorite parts of my day is walking my pit bull mix, Trisha. So I figured it was time to spread the love and walk with other furry friends. I have been a dog mom for 7 years and have experience caring for dogs of all sizes (everything from my parents 5lb Yorkipoo to a 100lb labradoodle). I love being outdoors and I will be vigilant and responsible at all times with your dog. Prior to training my dog, I knew what it was like to walk with a reactive, excitable dog, so I am comfortable with dogs who are still learning and growing. I will keep your dog safe and return them happy and tired-out! I’m a fun and flexible sitter, and guarantee that you and your dog will be stress-free with me! I will send you updates with video/photo attachments with fun stories about what we did and how your furry friends are doing so you never have to worry. I am available to walk or visit your fur baby during the day and during some evenings Monday through Friday. I am available some weekends. I have years of experience keeping dogs of all kinds and sizes safe on walks and in the home. Playing and exercising your dog, along with basic obedience training if requested, are my goals - but keeping your dog safe, happy, and healthy is my promise!

Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
141 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie was great! Kitties were very well taken care of. Pictures were sent throughout of them playing, having treats, etc which was nice to see while we were away! Would definitely use her again!

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Lindsey M.
Sitter Profile Image: Carrianne L.
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Carrianne L.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
169 reviews
42 repeat clients
20 years of experience
Shorewood, WI, 53211

Carrianne was amazing with my cat! My cat has never come out for any sitter before, but with Carrianne he even allowed some pets! She was punctual, reliable and personable, clearly made my cat feel very comfortable! I will definitely be booking her again for my next trip!

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Alexandria L.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
202 reviews
60 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was so fabulous! I couldn’t recommend her enough. Very communicative with us - we have a cat with medication needs so updates are important and she made us feel at ease. Will absolutely use her again! 😊

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Jenna B.
Sitter Profile Image: Hope S.
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Hope S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
51 reviews
24 repeat clients
15 years of experience
Riverwest, Milwaukee, WI, 53212

Best sitter ever! Very grateful for all of Hope’s help feeding & playing with my kitty while I’m away. Hope leaves very detailed notes and many photos, which is very helpful knowing my pet is in good hands. My kitty loves Hope and will cuddle with her when she comes to visit, which is a sign of a loving sitter. 1000% rebooking & recommend Hope to all!!

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Sarah R.
Sitter Profile Image: Hanna C.
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Hanna C.
from
$15
per visit
4.9 out of 5 stars
42 reviews
5 repeat clients
10 years of experience
Riverwest, Milwaukee, WI, 53212

Hanna was such a great drop-in sitter for my cat Glenn. She provided updates and pictures everyday which gave me peace of mind while I was away. I will absolutely use her again 😊.

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Brianna S.
Sitter Profile Image: Kim S.
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Kim S.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
152 reviews
38 repeat clients
30 years of experience
Glendale, WI, 53217

Kim is prompt, communicative, and accommodating to our cats’ needs. Thank you, Kim, for providing peace of mind when we need to go out of town.

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Jane J.
Sitter Profile Image: Abigail L.
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Abigail L.
from
$20
per visit
5.0 out of 5 stars
408 reviews
112 repeat clients
7 years of experience
Riverwest, Milwaukee, WI, 53212

Abigail is an incredible dog sitter! She is personable, detailed, and timely. She always completed detailed notes, sends a variety of photos of her visit with the pet, and asks great questions to make sure she is able to give the best care possible to your pet! Our dog is a puller on walks and is high energy but Abigail has the skills to be successful with these types of pets. Our home was kept very neat and orderly as well which we appreciated. She was also very communicative and responsive. We will definitely be rebooking with Abigail!

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Angela J.
Sitter Profile Image: Carole C.
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Carole C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
181 reviews
39 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Carole was so wonderful taking care of our Maggie! She was very timely and responsive, sent us lots of pictures and videos, and listened to exactly what our girl needed. Even when our flight got delayed multiple hours, she was willing to stop in for an extra visit on such short notice. Couldn’t recommend Carole enough! Thank you so much!

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Reeve W.
Sitter Profile Image: Qian D.
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Qian D.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
2 years of experience
Lower East Side, Milwaukee, WI, 53202

I'm super grateful to have found Qian as a first-time user of Rover! Can't thank her enough! She was very sweet and kind to my kitty. She did a great job completing all the tasks and even added multiple pictures of my kitty to the drop-in! Communication with her is very easy, too! I would definitely request her again and recommend her to anyone!

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Pei Hsuan C.
Sitter Profile Image: Abigail B.
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Abigail B.
from
$18
per visit
15 years of experience
Milwaukee, WI, 53206

About: I have grown up with cats and dogs my whole life and have had the honor of caring for others pets as well! I have cared for a wide variety of animals including dogs, cats, horses, and birds! I am currently in school and find myself with a lot of free time! I enjoy going for walks and playing with my cat that lives with me! I live in a gated community with a fenced in dog yard! I know lots of great walking areas to bring your dogs too for a little fun adventure!

Sitter Profile Image: Nevaeh T.
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Nevaeh T.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
6 years of experience
Milwaukee, WI, 53211

Nevaeh was awesome! She sent us text updates including pictures/videos the whole time giving us peace of mind. Our dog Mallie loved her! Would definitely recommend!

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Cheyenne D.
Sitter Profile Image: Megan K.
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Megan K.
from
$26
per visit
5.0 out of 5 stars
24 reviews
6 repeat clients
22 years of experience
Shorewood, WI, 53211

About: I am a 29-year-old from Minnesota. I went to the University of Wisconsin, and am currently a Registered Nurse! I grew up with a black standard poodle from ages 3-19, and an apricot standard poodle from ages 19-27. I now have my own golden doodle named Sonny. I love playing, walking, and just hanging out with dogs as often as possible; they always brighten my day. I am willing to cuddle, play fetch, or give your dog(s) treats as often as they would like. I promise to respect your pet(s) and home and do a great job. I love dogs of all kinds and am always excited to meet new puppy pals! I look forward to meeting you and helping you take care of your furry family member. I work a typical Monday to Friday, 8-5 job. It is remote, so I am typically working from home, although I occasionally have to travel outside of the state for work. If your dog is with me you can be assured their needs will be met! I will make sure they are respected and given the proper attention they need. :)

Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
51 reviews
18 repeat clients
40 years of experience
Murray Hill, Shorewood, WI, 53211

Melissa dropped in to check on my 2 cats for four days. She was kind, dependable and responsible which gave me peace of mind, especially considering one of my cats is elderly and needs daily medication.

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Lisa O.
Sitter Profile Image: Mikalanne T.
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Mikalanne T.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
49 reviews
16 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

About: I have grown up with dogs all my life. Every time I get the opportunity to watch a fur baby, I treat them like they are my own. I have done some dog/puppy training as well, and I've always gotten great reviews on what one's pet can do by the time they go home (If interested) My schedlue is fairly flexible. I am able to move clients around depending on your availability. This is my full-time gig as of now, so I take lots of pride in the care I provide to your pet(s). I have currently moved to Riverwest, this came with a fenced in backyard (yayyyy)! I live close to lots of parks, dog park (Rover west), and trails.

Sitter Profile Image: Jessica B.
Verified Enhanced Background Check
Jessica B.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
12 reviews
7 repeat clients
16 years of experience
Borchert Field, Milwaukee, WI, 53206

About: I have hands-on experience caring for dogs of all sizes, ages, and energy levels. I'm comfortable managing multiple dogs at once, maintaining routines, and ensuring each dog feels safe, exercised, and cared for. I prioritize calm, structured walks, positive reinforcement, and clear communication with pet parents. I can take the on potty breaks as often as needed as I work from home. I also have experience with overnight boarding, feeding schedules, medication, leash manners, and providing companionship throughout the day. I have a small friendly dog named Bob who gets along well with other dogs. With owner permission, Bob can join walks to provide socialization and companionship which is especially helpful for dogs with anxiety or who enjoy gentle interaction. Safety, your dog’s comfort, and individualized care are always my top priorities. My daily routine balances client care with my own dog's needs. I schedule every morning, midday, and evening walks, ensuring every dog receives attention, exercise, and socialization while my small, friendly pup joins safely when appropriate. I provide attentive, loving care for pets in my home including feeding, walks, playtime, and safe socialization. My small, friendly dog can join walks for companionship and comfort with owner's permission.

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Over 1
pet parents in Williamsburg have booked pet sitting

Williamsburg pet parents share their Rover experiences

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5.0 out of 5 stars

Rayanne is extremely helpful and easy going, she has eased my mind about the care of my cat while being out of town. I will be continuing to go through her for my cat’s care when I’m out of town, I highly recommend her for your pets care!

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

Nothing but good things to say about Abby. She was my first ever cat sitter from Rover and the experience was so smooth thanks to her. She’s very flexible and very eager to learn about your pets personality. Book her!!

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Amin
Drop-In Visits
5.0 out of 5 stars

Jackie was very kind! I appreciated her looking after my fur babies while I was gone. I always loved the picture updates!

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

Angela was great. The animals loved her and she left good descriptions and pictures with every visit.

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

Whitney was awesome with the two cats. The two cats were very comfortable with her. Nick and Sam can be challenging and Whitney kept us informed with clear communication. She was very caring towards the cats. I will definitely ask her to care for Nick and Sam again!

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Anne D.
Drop-In Visits
5.0 out of 5 stars

Lisa was outstanding with our doggies! Great communication with us and paid close attention to the little details that made them feel comfortable. Would highly recommend her!

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

Qian took great care of my cat while I was away. She came to my house every day for a week!, refreshed his water, cleaned the litter box, and spent time playing with him. She was reliable, consistent, and made me feel very comfortable knowing my cat was nice and cared for. I really appreciated her help and would definitely recommend her to anyone looking for a trustworthy pet sitter!

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

Jessica is amazing. She is very conscientious and caring. She has taken great care of my senior cat, Rosie. I’ve already booked her again. Her communication is timely and she is very prompt. So happy to have her. Real peace of mind when traveling knowing Jessica is caring for Rosie.

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

Ilene is the best and I'm so glad we found her. My girls love her, even abandoning their favorite food in favor of play time. She's great at communication and provides the best visit summaries every day. So grateful!

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

We loved having Elizabeth as a rover for the past year and half. Posie was always excited to see Elizabeth and she always communicated quickly with me for any bookings and details. I would highly recommend!!

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Cassie D.
Drop-In Visits
5.0 out of 5 stars

Nicole takes such good care of my cats. I almost think they look forward to me going on vacations, so they can hang out with her

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

It’s hard to be away from an elderly cat with health issues but Hope makes sure he’s very well taken care of and always brings me peace of mind while I’m away!

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

Nevaeh was awesome! She sent us text updates including pictures/videos the whole time giving us peace of mind. Our dog Mallie loved her! Would definitely recommend!

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Cheyenne D.
Drop-In Visits
5.0 out of 5 stars

This was our first booking with Carrianne. She was great! She asked good clarifying questions during our meet and greet to make sure she fully understood how to care for our kitty, and was reliable and timely during the booking. We fully trusted her to take care of our anxious cat. We would love to book with her in the future!

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

This is the second time that I book with Katelyn, she’s the best taking care of Amy, my old lady cat 🐈. She is so careful with her and I’m sure she will be with your pets to. Hope next time I’m on holidays Katelyn would be able!

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

Bria is really responsible and takes amazing care of our Frenchie. I can always trust our dog in her care.

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

Megan was fantastic! Buddy was so happy hanging out with her. She sent lots of photos and videos and took great care of him!

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Susannah K.
Drop-In Visits
5.0 out of 5 stars

Awesome per usual!! I love reading Jensen’s updates on goofy stuff my pup does, and he always provides lots of pictures!!

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

Travis is always awesome! So appreciative that he could help us out last minute. The cats appreciate him too!

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

Jasmine has been a great sitter for my pups. I’ve rebooked with her several times and she’s always done an awesome job. I never worry about my dogs being well cared for.

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Brandi R.
Drop-In Visits
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How Rover works

  1. 1. Search

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

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets 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!

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your pet 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.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Williamsburg 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 Williamsburg.

Rover makes it easy to find Williamsburg 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.