Dog Boarding Chesterton

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Sitter Profile Image: Catherine J.
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Catherine J.
from
$35
per night
4.9 out of 5 stars
61 reviews
20 repeat clients
60 years of experience
Valparaiso, IN, 46385

Catherine was amazing and gave me a peace of mind sitting Dilly! She is very warm and loving, and kept us informed the entire stay with plenty of pictures! Dilly was happy and energetic at pick up and felt at home with Catherine! We will definitely have Dilly stay with Catherine again!

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Candice M.
Sitter Profile Image: Janis & Devin R.
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Janis & Devin R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
60 reviews
31 repeat clients
45 years of experience
MICHIGAN CITY, IN, 46360

My dog has horrible separation anxiety so I dread trips away from home. Using the warm and cozy home of Janis and Devin was the perfect solution. I received multiple pictures every day. I could tell my dog was happy and feeling a part of the family. When I picked him up he was not crazed and inconsolable. He also has not been extra anxious at home as he usually gets. I will use Janis and Devin again and again. I have the highest esteem and praise for their business. I HIGHLY recommend!

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Shaneta P.
Sitter Profile Image: Giannina G.
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Giannina G.
from
$30
per night
4.9 out of 5 stars
91 reviews
39 repeat clients
5 years of experience
Miller Beach, IN, 46403

She was absolutely amazing with my dog while I was gone for work for a week. She kept me updated throughout the entire stay and even sent pictures of my sweet girl enjoying herself. I would definitely recommend her to anyone!! I will be using her boarding services again in the future :)

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Ashley B.
Sitter Profile Image: Jordan C.
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Jordan C.
Star Sitter
from
$50
per night
4.9 out of 5 stars
301 reviews
127 repeat clients
12 years of experience
Portage, IN, 46368

Each pet has different needs and as a pet parent I need to find placement to meet those needs. After several placements that were horrific to subpar, I was happy to find Jordan her pack and family. My dog was happy and well taken care of at Jordans house. Not only will I be rescheduling boarding I will also schedule daycare for my dog to have playdates with Jordans pack.

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Judy R.
Sitter Profile Image: Mary S.
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Mary S.
Star Sitter
from
$40
per night
4.9 out of 5 stars
235 reviews
81 repeat clients
20 years of experience
Michigan City, IN, 46360

Mary and Marty always take great care of our dog. They’re easy to communicate with… quick to respond and keep us up to date on how Sully’s stay with them is going. Highly recommend!

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Tina S.
Sitter Profile Image: Nancy & Mark N.
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Nancy & Mark N.
Star Sitter
from
$45
per night
5.0 out of 5 stars
181 reviews
75 repeat clients
25 years of experience
Valpairso, IN, 46385

Our experience with boarding our dog with Nancy couldn’t have been any more perfect. On top of her personal kindness, the daily photos & reassurance of our dog’s stay was extraordinary. I don’t have enough positive words to explain our experience. Highly recommend booking with Nancy!

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Brittany W.
Sitter Profile Image: Jessica H.
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Jessica H.
from
$29
per night
15 years of experience
Portage, IN, 46368

About: I’ve been surrounded by animals my entire life, and dogs have always had a special place in my heart! Growing up, my family had dogs, horses, goats, chickens, cats, birds, fish—you name it. Caring for animals has always been second nature to me, and over the years I’ve become the go-to pet sitter for friends and family whenever they go on vacation. I understand that every dog is unique, whether they’re full of energy and love long walks or prefer cuddles and a relaxing day at home. My goal is to make your pup feel safe, loved, and comfortable while you’re away by keeping their routine as normal as possible. You can expect plenty of playtime, belly rubs, potty breaks, and lots of love and attention. I treat every dog as if they were my own and will keep you updated so you can enjoy your time away with peace of mind, knowing your furry family member is in good hands! I currently work full-time from 8:00 AM to 4:30 PM and have an hour commute each way. Because of this, I offer boarding for pets who are comfortable being alone for an extended period during the workday. I am fully available on weekends and can dedicate plenty of time to your furry family members! I also offer evening dog walks and drop-in visits after work. Please feel free to reach out if you have any questions about my schedule or your pet’s specific needs—I’m happy to accommodate whenever possible! Your pet will be welcomed into a safe, loving home away from home! I live in a top-floor apartment with carpeted stairs and plenty of windows, perfect for curious pups who love to look outside and watch the world go by. There’s also a private dog park directly across the street from my complex, giving your dog a great place to play and burn off some energy. My neighborhood is quiet and pet-friendly, making it ideal for long walks and plenty of sniffing adventures. I make sure every pet gets lots of attention, playtime, potty breaks, and, of course, treats (with owner approval!). My goal is to make your pet feel comfortable, loved, and cared for while you’re away, treating them like part of my own family.

Sitter Profile Image: Meredith M.
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Meredith M.
from
$48
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
35 years of experience
Valparaiso, IN, 46383

Meredith was just amazing. She handled my crazy dog along with her family and dogs like a champ. My pup seemed to greatly enjoy herself. Along with a happy pup, my dog came home with a few more manners. We will use her in the future for sure. 😊

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Abbey S.
Sitter Profile Image: Shawne S.
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Shawne S.
Star Sitter
from
$35
per night
5.0 out of 5 stars
89 reviews
33 repeat clients
20 years of experience
Michigan City, IN, 46360

Shawne and her husband were very welcoming and ready for the dogs upon arrival. They were receptive to the dogs' routines and ready with kennels. They have outdoor space and live in a nice neighborhood. Shawne was really great at keeping us updated with texts and pictures. The boys were happy and had so much fun that they were exhausted when we got them back from all of the fun activities.

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Lucy B.
Sitter Profile Image: Carmelle Joy H.
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Carmelle Joy H.
Star Sitter
from
$30
per night
4.9 out of 5 stars
106 reviews
53 repeat clients
8 years of experience
GRIFFITH, IN, 46319

Joy was fantastic, very personable and took great care of my dogs! She is flexible with meet and greets and professional during the whole process (no matter how many questions/directions I threw at her!). We will absolutely book with her again!

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Danni M.
Sitter Profile Image: Jesseeka & John G.
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Jesseeka & John G.
from
$45
per night
4.9 out of 5 stars
78 reviews
17 repeat clients
20 years of experience
Merrillville, IN, 46410

I recently boarded my dogs with Jesseeka, and I couldn't be happier with the experience! She was absolutely fantastic—sending plenty of pictures, responding quickly to any questions, and making sure my dogs were well cared for. She even gave them baths, which was such a thoughtful touch! One of my dogs is quite skittish, and she went above and beyond to make her feel comfortable. Another has some behavioral quirks, and she handled him with patience and skill. It’s clear she truly cares about the dogs she watches. I highly recommend her to anyone looking for a reliable, caring, and professional pet sitter. I’ll definitely be booking with her again!

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Jessica & Michael W.
Sitter Profile Image: Bernice S.
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Bernice S.
Star Sitter
from
$35
per night
5.0 out of 5 stars
116 reviews
32 repeat clients
50 years of experience
Merrillville, IN, 46410

Bernice did an absolutely amazing job caring for my fur baby this past weekend! I was pretty nervous since he’s newly adopted, but she quickly put my mind at ease. Her communication was excellent—she sent daily pictures and kept us updated on how his day was going, which meant so much to me. It was clear he felt completely comfortable and at home—honestly, he didn’t even want to leave! Her fenced-in backyard was a huge bonus and gave him plenty of space to play safely. I couldn’t have asked for a better experience. Bernice is the only person we’ll be booking with going forward!

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Brittney T.
Sitter Profile Image: Angelique V.
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Angelique V.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Westville, IN, 46391

Angelique was wonderful to our little meatloaf while we were out of the country. She sent us many photos and kept us updated on anything new. We will definitely go with Angelique if we need a dog sitter in the future.

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Amanda D.
Sitter Profile Image: Kelly P.
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Kelly P.
from
$29
per night
10 years of experience
Portage, IN, 46368

About: I've been taking care of dogs & cats my entire life. I have experience as a vet assistant. Animals are my passion and not only do I love providing a loving home for my animals but I also know how hard it is to balance work and life in general when you have pets so I want to be able to care and help you with your fur babies as well! I'm currently only working part time so I have a lot of free time to care for your fur babies ! My schedule is pretty open so on my days off I can take last minute requests . I also enjoy being outdoors even if it's just sitting in the backyard with the dogs I have a fenced in yard with a loving yellow Labrador ! Your pup will have fun and will stay safe with plenty of exercise! I do not go on walks without a leash or without your consent.

Sitter Profile Image: Madelyn O.
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Madelyn O.
from
$40
per night
5.0 out of 5 stars
21 reviews
6 repeat clients
10 years of experience
Chesterton, IN, 46304

My little Delilah felt right at home when we had our Meet and Greet. I had no concerns about leaving her with Madelyn after that. She was still excited to see me when I picked her up, but not so excited that I worried she wanted to leave and had a bad time. I have no doubts that Delilah was well cared for while I was away!!

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Sarah W.
Sitter Profile Image: Monika H.
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Monika H.
from
$45
per night
5.0 out of 5 stars
6 reviews
1 repeat client
13 years of experience
Crown Point, IN, 46307

monika was great with our Mia! she came home very happy. i got daily updates also with pictures.

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Pamela N.
Sitter Profile Image: April Y.
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April Y.
Star Sitter
from
$56
per night
5.0 out of 5 stars
48 reviews
16 repeat clients
15 years of experience
Merrillville, IN, 46410

April is the best! I bring my dog to her instead of leaving him with family because he loves her house and dogs so much. Great communication and clearly a massive dog lover.

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Alyssa M.
Sitter Profile Image: Clay P.
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Clay P.
from
$31
per night
5.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Beverly Shores, IN, 46301

About: I've grown up living with dogs and have been the primary trainer for my family's dogs. I do pretty well working with new pets and can handle full size dogs. I'm an engineer who gets home from work around 4 or 5PM. My weekends are empty 3/4 weekends a month. I can do overnights on Sunday and during the work week if your dog is used to being alone 9-5. I have a small yard, and live next to the beach. I typically walk my dog to the beach 2-3 times a day on the weekend and she swims often. I usually use a harness to walk dogs, never leave them unattended outside since I have no fence. Make sure they have food twice a day and water always full.

Sitter Profile Image: Sharon B.
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Sharon B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
2 repeat clients
20 years of experience
Homewood, IL, 60430

This was my first time using Sharon and all went well. She sent photos and videos of Lily and took Lily on frequent walks. She was quick to respond to my texts. I really appreciate Sharon’s responsible and professional nature. And when I picked up Lily at the end of her stay, Sharon gifted her a bag of treats and toys and a thank you note! I will definitely use Sharon again.

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Beth L.
Sitter Profile Image: John J.
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John J.
from
$40
per night
20 years of experience
Schererville, IN, 46375

About: I have taken care of animals my whole life. Family and friends have relied on me for decades to take care of their animals. Growing up on a farm helped give me a lifelong affinity for animals. I’m a teacher who is off all summer. I have plenty of time to fill and would love to look after your animals, either in my home, as a drop in, or just a walk. I have a fenced in backyard, two amazing labs who love other dogs, and a wife and daughter who love dogs as much as I do.

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The median cost per night for dog boarding in Chesterton is $45

Dog parents share their Rover experiences - Chesterton

1 / 1
5.0 out of 5 stars

Willow and Kevin were amazing! They made drop off and pick up with Teddy a breeze. He was spoiled and well taken care of while we were away! I loved getting photo updates and messages! This was my first time using rover and a last minute booking. Willow was so gracious taking Teddy into her home with Jules and Duke! It eased my mind to know he was getting so much love and attention! I would definitely recommend Willow and would book again! She is so sweet and was so attentive to Teddy's needs. He even got a parting gift complete with a beautiful bow and treats! Thank you Willow and Kevin!

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Amanda M.
Boarding
5.0 out of 5 stars

Madison provided excellent care for our dog while we were gone. Good updates with pictures! Even did a grooming session so I didn have to take her which was a huge help! Highly recommend!

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Mary C.
Boarding
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How Rover works

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Sitters in Chesterton average 12
repeat dog boarding clients

FAQs for Dog Boarding - Chesterton

Frequently asked questions about Rover

The average cost for Dog Boarding in Chesterton on Rover is $44.4 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .

As of July 2026, there are 418 sitters on Rover offering Dog Boarding across Chesterton. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

98% of Chesterton sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Chesterton landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chesterton home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Chesterton.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Chesterton sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in IN ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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