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.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

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.

1 / 1
Sitter Profile Image: Madison G.
Verified Enhanced Background Check
Madison G.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
15 years of experience
Porter, IN, 46304

Maddie made me feel that my precious cat was going to be well-taken care of while we were away, and she did not disappoint. Prompt and courteous, I have already recommended her to a neighbor. I hope she will be able to allow me to travel without worry many more times in the future.

Profile image
Laura S.
Sitter Profile Image: Mary R.
Verified Background Check
Mary R.
from
$15
per visit
5.0 out of 5 stars
11 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!

Profile image
Steve W.
Sitter Profile Image: Emily G.
Verified Background Check
Emily G.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
245 reviews
168 repeat clients
16 years of experience
Chesterton, IN, 46304

Emily was perfect! She was very trustworthy in our home with our fur babies! She updated us with lots of messages and even photos! I will definitely use her again in the future!

Profile image
Jessica S.
Sitter Profile Image: Grace R.
Verified Enhanced Background Check
Grace R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
29 reviews
7 repeat clients
10 years of experience
Porter, IN, 46304

Grace is wonderful! She did amazing with our cat and took great care of our apartment. She provided fun visit reviews with cute pictures too! We’ve already booked her for more drop-in’s, so we highly recommend her to anyone. Thank you so much!

Profile image
Caitlin C.
Sitter Profile Image: alexis c.
Verified Enhanced Background Check
alexis c.
from
$16
per visit
4.8 out of 5 stars
49 reviews
20 repeat clients
6 years of experience
portage, IN, 46368

Alexis did a wonderful job communicating throughout the day. I loved receiving updates and pictures at every visit. Knowing Bruce was in such good hands made being away so much less stressful.

Profile image
Cheyenne M.
Sitter Profile Image: Melanie C.
Verified Enhanced Background Check
Melanie C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
73 reviews
28 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!

Profile image
Cassie G.
Sitter Profile Image: Julie F.
Verified Enhanced Background Check
Julie F.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
427 reviews
55 repeat clients
17 years of experience
Valparaiso, IN, 46385

Julie took wonderful care of our 3 kitties, giving us such peace of mind while we were out of town. We knew they were in great hands, and Julie went above and beyond!! We’ll gratefully rebook with Julie anytime we have to go out of town in the future. Thank you so much Julie!!!

Profile image
Heather M.
Sitter Profile Image: Aubrey R.
Verified Background Check
Aubrey R.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Chesterton, IN, 46304

Duke was well taken care of by Aubrey and he got plenty of play time. Duke made up to Aubrey very quickly at the meet and greet which let me known he would be happy to spend time with her!

Profile image
Chris B.
Sitter Profile Image: Chyanne H.
Verified Enhanced Background Check
Chyanne H.
from
$18
per visit
5.0 out of 5 stars
19 reviews
7 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

Profile image
Roe H.
Sitter Profile Image: Sydney T.
Verified Enhanced Background Check
Sydney T.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
16 years of experience
Valparaiso, IN, 46385

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

Profile image
Pat I.
Sitter Profile Image: Jen M.
Verified Enhanced Background Check
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

Profile image
Anthony F.
Sitter Profile Image: Emma & Timothy H.
Verified Enhanced Background Check
Emma & Timothy H.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
23 reviews
8 repeat clients
27 years of experience
Valparaiso, IN, 46385

Emma and Timothy have watched my dogs two times now and I couldn’t ask for anyone better! My timid German shepherd warmed up to them quickly and my overly excited Shepard Pit mix loves them! Emma and Timothy communicate often and send the cutest pictures! I know my babies are in good hands when I book them.

Profile image
Natalie R.
Sitter Profile Image: Alexia W.
Verified Enhanced Background Check
Alexia W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
22 reviews
3 repeat clients
6 years of experience
Valparaiso, IN, 46383

About: Ensure your pet feels safe and loved even when you're not home. My dedicated pet sitting services allow your furry friend to stay in the comfort of their own space. From regular dog walking to attentive care for your pets, I cater to their needs while you're out of town or just away for the day. With a focus on individual attention and affection, your pets will enjoy a stress-free experience. Book with me and give your pets the care they desereve! Pet care fits naturally into my routine, allowing me to give my full attention to each animal I look after. I visit clients’ pets before I start my work day and return directly afterward to ensure they stay on their regular schedule. On weekends — and on weekdays when I have extra time — I go beyond the basics by adding extra playtime, enrichment activities, or simply quality companionship for pets who value one-on-one attention. Whether they’re energetic explorers or calm cuddlers, I make sure each pet feels supported, stimulated, and loved every day their family is away. When caring for pets in their home, I make sure their routines and comfort come first. I provide fresh food and clean water, ensure they have proper potty breaks, and clean up any soiled areas to keep their space tidy and stress-free. Each visit includes 30 minutes to an hour of engagement — whether that’s active play, enrichment activities, or simply relaxed cuddle time depending on what the pet enjoys most. I also handle medication when needed, maintain clean litter boxes, and pay close attention to their overall well-being. My goal is to make every pet feel secure, comfortable, and loved while their family is away.

Sitter Profile Image: Taylor H.
Verified Enhanced Background Check
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: Hannah R.
Verified Enhanced Background Check
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!

Profile image
Angie L.
Sitter Profile Image: Sabrina S.
Verified Enhanced Background Check
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.

Profile image
Emily S.
Sitter Profile Image: Emily R.
Verified Enhanced Background Check
Emily R.
from
$20
per visit
15 years of experience
Chesterton, IN, 46304

About: I had a 100 lb mastiff all 8 years of his life on earth and trained him extensively. He walked well on a leash but even when he developed leash aggression later on in life and he pulled I had the strength to contain him. I'm very used to extra large breeds and love them dearly! I also potty trained and crate trained him as a puppy. I am a self-employed wedding photographer that works from home and only works seasonally so I'm very flexible! I have two kittens at home so caring at the client's home is ideal unless the dog is cat-friendly. :) I have a fenced in yard. Whether I am in my home or the client's home, I love walking with dogs and miss it so much since my dog died last June. It brings me joy to give dogs the exercise they need and stay healthy myself in the process!

Sitter Profile Image: Keely T.
Verified Enhanced Background Check
Keely T.
from
$20
per visit
5.0 out of 5 stars
1 review
1 repeat client
3 years of experience
Chesterton, IN, 46304

Keely was pleasant to communicate with, kept the house as clean and pets were happy so 👍👍 up. I'll be booking her again for my next out of town adventure, thnx Keely :)

Profile image
Blake L.
Sitter Profile Image: Kortney R.
Verified Enhanced Background Check
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!

Profile image
Kate D.
Sitter Profile Image: Nakayla J.
Verified Enhanced Background Check
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!

1 / 1
View more sitters

Over 104
pet parents in Chesterton have booked pet sitting

Chesterton pet parents share their Rover experiences

1 / 1
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.

Profile image
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.

Profile image
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

Profile image
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!

Profile image
Amber W.
Drop-In Visits
1 / 1
Find pet care near you

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 $25

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 7
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 May 2026 was about $25 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 May 2026, there are 84 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, 89% of Chesterton pet sitters respond in under an hour.

Pet sitters with repeat customers have an average of 7 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 84 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.