Pet Sitting in Chesterton

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 Chesterton 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: Grace R.
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Grace R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
31 reviews
8 repeat clients
10 years of experience
Porter, IN, 46304

Grace was awesome with Ares! He had a blast with her and she communicated well throughout the whole process. She’s very flexible too and will work to your convenience. 10/10 would recommend!

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Victor T.
Sitter Profile Image: Mary R.
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Mary R.
from
$15
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
8 years of experience
Chesterton, IN, 46304

Patient and kind with a nervous dog. Very appreciative. Thank you for the gentleness!

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Steve W.
Sitter Profile Image: alexis c.
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alexis c.
from
$16
per visit
4.8 out of 5 stars
50 reviews
20 repeat clients
6 years of experience
portage, IN, 46368

Alexis was awesome and kept my Cali company while I had to be away. Cali sure is enjoying the toy Alexis gave her. I will be sure to use Alexis anytime I need assistance with Cali.

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Donna D.
Sitter Profile Image: Melanie C.
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Melanie C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
75 reviews
30 repeat clients
15 years of experience
Portage, IN, 46368

Melanie went out of her way to come meet Olivia and us before her time to dog sit. She was flexible, communicated very well and did an excellent job. This was our first time to use Rover and we are hooked! Thank you!

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Cassie G.
Sitter Profile Image: Hannah R.
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Hannah R.
from
$17
per visit
5.0 out of 5 stars
38 reviews
10 repeat clients
24 years of experience
Chesterton, IN, 46304

Hannah helped us out on Christmas evening when we were going to be away from our house for 12 hrs. We so appreciated the extra mile Hannah went to come a week before Christmas to meet our dogs and speak with us personally so we would feel comfortable leaving our two greyhounds in her care for a bit. She communicate well and responded in a timely manner when we first were setting up the visit with her. We will definitely use Hannah again and absolutely recommend her services! Thanks again Hannah, you helped make our Christmas less stressful!

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Angie L.
Sitter Profile Image: Julie F.
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Julie F.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
444 reviews
57 repeat clients
17 years of experience
Valparaiso, IN, 46385

Thank you so much! You are an awesome sitter, and I would recommend you to anyone! You take special care with all my babies! I love the pictures! Thank you again!

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Sonya M.
Sitter Profile Image: Skyler V.
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Skyler V.
from
$20
per visit
5.0 out of 5 stars
1 review
2 repeat clients
5 years of experience
Portage, IN, 46368

I would highly recommend Skyler, reasonably priced, reliable and very accommodating!

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Melissa V.
Sitter Profile Image: Madison G.
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Madison G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
15 years of experience
Porter, IN, 46304

Madison did an amazing job taking care of our cats while we were out of town. She is kind, respectful, responsive and responsible! She sent pictures and updates and even brought in our packages. My cats were well taken care of and the litter box was obviously thoroughly cleaned each time.

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Samantha K.
Sitter Profile Image: Jen M.
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Jen M.
from
$17
per visit
5.0 out of 5 stars
30 reviews
5 repeat clients
20 years of experience
Portage, IN, 46368

Jen is top quality dog care. She puts her heart and soul into your pet. Prezi loves her. I highly recommend Jen. I couldn't ask for a better person to take care of my baby girl. Thank you for being so good Jen

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Anthony F.
Sitter Profile Image: Sydney T.
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Sydney T.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
16 years of experience
Valparaiso, IN, 46385

Sydney has been a great help to a disabled cat owner.

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Pat I.
Sitter Profile Image: Sabrina S.
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Sabrina S.
from
$22
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
7 years of experience
Portage, IN, 46368

Sabrina did a great job dropping in on our girls. She fed them breakfast, gave them pets and let them out for potties. Our girls were happy and well cared for.

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Emily S.
Sitter Profile Image: Kortney R.
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Kortney R.
from
$25
per visit
5.0 out of 5 stars
34 reviews
11 repeat clients
14 years of experience
Chesterton, IN, 46304

Kortney is so great with both my dogs who are an absolute handful!

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Kate D.
Sitter Profile Image: Chyanne H.
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Chyanne H.
from
$18
per visit
5.0 out of 5 stars
21 reviews
8 repeat clients
15 years of experience
Valparaiso, IN, 46383

Always on time. Spent quality time and played with my dog. Made sure she had plenty of belly-rubs and attention. Also made sure she had fresh water before leaving

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Roe H.
Sitter Profile Image: Lexi W.
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Lexi W.
from
$20
per visit
5.0 out of 5 stars
2 reviews
2 years of experience
Chesterton, IN, 46304

About: I have had 3 dogs in my whole life and I’ve loved them all. I love taking care of animals. I have experience watching both my friends and families pets while they were on different vacations. I am currently in college and am currently in online classes so I have a pretty free schedule and am looking to occupy myself with making money and loving on some cute puppies! I feed my dog and groom him. I give him bathes and take him on walks daily. I take my puppy to have play dates with his friends too.

Sitter Profile Image: Laylani O.
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Laylani O.
from
$15
per visit
5.0 out of 5 stars
1 review
3 years of experience
Valparaiso, IN, 46385

Laylani is amazing! Our pup LOVED her. She was dependable and caring and I felt so much better about being away. The communication and pictures were so reassuring and my kids excitedly awaited her reports. Highly recommend (just not on the days I need her 😂)!

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Billie B.
Sitter Profile Image: Lauren M.
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Lauren M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
11 years of experience
Valparaiso, IN, 46385

Lauren was wonderful--great communication and got several photos during her drop-in visit.

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Kathy S.
Sitter Profile Image: Taylor H.
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Taylor H.
from
$20
per visit
1 year of experience
Burns Harbor, IN, 46304

About: I love staying active and spending time outdoors. Your dog and I will have a great time on walks or runs together! And if you have a feline friend, I’m just as happy to relax and keep them company at home. I’m kind of a early morning person so I can take your pet out in the morning for their bathroom breaks walks on a nice afternoon I wake up at 5am to feed my cats breakfast Make sure they have their puzzles filled in the morning and night to keep them Occupied/busy. Clean their litter boxes every morning and before bed .

Sitter Profile Image: Hailey H.
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Hailey H.
from
$10
per visit
4 years of experience
Valparaiso, IN, 46383

About: I'm a lifelong pet owner with plenty of experience caring for different species of all ages. I'm super comfortable adapting to whatever specific care an animal needs. I am a college student with part-time jobs, which means my schedule is pretty flexible so I can easily adapt my hours to fit any routine and care needs I have two very friendly dogs and one social cat at my own home, so your pet will be in great company. If I'm caring for them at your home, I will follow all given instructions and spend quality time socializing with your pets.

Sitter Profile Image: Nakayla J.
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Nakayla J.
from
$20
per visit
10 years of experience
Portage, IN, 46368

About: I have taken care of animals for as long as I can remember! I I’ve taken a vocational course for veterinary & I’ve have pets of my own! I’m also working towards becoming a groomer so this is something to get my foot in the door of giving myself even more experience than I already have! I am comfortable around all dogs and am willing to adapt and learn how to best care for your animal. When I come to take care of, play with, and walk your animal I will dedicate my time to loving them as if they were my own! I would love to be able to take them to the dog park where they can also interact with other animals while you're away! I have two cat of my own, both are short haired cat’s I have one boy and one girl! They’re very cuddly and playful whenever they want to be lol! I am currently working this as part time! But, I’m still available for drop ins or house sittings when needed! I am also flexible and can accept last minute bookings. When in your home, I would love to take your fur babies for walks, to dog parks, anything you already do with them to make them the most comfortable! I would also love to spend time with your cats, feed them, play with them, my cats especially love the laser toy/ any hanging string! I will respect your home, whatever rules or things you typically have or want followed will be respected! I’m more than happy to ask any questions if I don’t understand something so they’ll be no missed communication! I want to make you and your furry babies as happy and as satisfied as possible! I'm currently working part-time, so I'll have plenty of time to play with your pups! I'm weekday’s and on weekends. Weekdays will typically be from 12pm-2:30, the times may change to longer hours depending on my job! Weekends: Saturday anytime throughout the day. Sunday: 4-10pm. I will take care of your pets based on your rules! If there’s a specific time you always feed your animal I will do the time asked for! When it comes to safety, safety is most important for me and your animal! I will keep your number in reach at ALL TIMES! If I notice the dogs getting aggressive i’ll try to calm the dog. If you have a fenced backyard i’ll make sure I watch your animal as they use the restroom or even just play around and keep an eye out for any signs of danger!

Sitter Profile Image: Katrina A.
Verified Enhanced Background Check
Katrina A.
from
$25
per visit
5.0 out of 5 stars
3 reviews
5 years of experience
Portage, IN, 46368

About: I've grown up around cats and dogs my entire life. I have pet-sat for people, walked numerous dogs from the shelters, and even fostered shelter cats in my home. I am comfortable with all ages of pets and all sizes. I would love to be available for your needs all weekdays past 4pm. I do work full-time, but would be willing to do whatever I can to help you. I can care for your pets in your home whether it's walking, playing, feeding, or caring for them. I am okay with bathing and brushing the pet. Also okay with taking in the car with me if we go to the dog park.

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Over 106
pet parents in Chesterton have booked pet sitting

Chesterton pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Had another fabulous set of drop-in visits with Grace and our cat absolutely loves her! Thank you so much for your help and care!

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

Madison did an amazing job taking care of our cats while we were out of town. She is kind, respectful, responsive and responsible! She sent pictures and updates and even brought in our packages. My cats were well taken care of and the litter box was obviously thoroughly cleaned each time.

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

Kelli was great! She checked in with Pumpkin and Peaches every day, and I felt a tremendous peace of mind with her taking care of my kitties. Thank you, Kelli! Her personality is so sweet, warm, and welcoming. She treated my kitties like they were her own.

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

Madison came to visit our pup a few times a day while we were away. She sent photos and took great care of her. We will be using her for future trips

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

Vanessa was amazing with Ellie! She made sure she had good walks and took time to play ball with her. Vanessa is very friendly, professional, and responsive. She took the time to meet her beforehand to make sure Ellie was comfortable. We enjoyed reading about Ellie’s time with Vanessa and loved seeing our fur baby in some pictures! This was our first time leaving her in the care of another in our home and Ellie seemed happier and more comfortable than boarding or being left with family members. Highly recommend!

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Amber W.
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!

The median cost per night for pet sitting in Chesterton is $23

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 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.

Sitters in Chesterton average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Chesterton on Rover as of Jun 2026 was about $23 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Chesterton 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.

As of Jun 2026, there are 95 pet sitters in Chesterton. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Chesterton pet sitters respond in under an hour.

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

Rover makes it easy to find Chesterton 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

There are 95 pet sitters in Chesterton on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.

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.