Dog Boarding Chesterton

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Over 16
pet parents in Chesterton have booked dog boarding

Chesterton, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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

“Ellie loved visiting with Catherine again. With Catherine I know she's is taken care of and will use her for our next trip. Communication is always great and shr sends lots of pictures.”

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Cassandra K.
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
• 200 reviews
82 repeat clients
25 years of experience
Valpairso, IN, 46385

“Using Rover was a last minute option for me prior to going out of town for a couple of days. I lucked out with Mark and Nancy! My dog was cared for in the same way I would care for him, I was sent pictures and a video, and they were beyond understanding when my return flight was continuously delayed. Knowing my dog was safe and happy took so much of the stress of traveling away and I will be forever grateful to them!”

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Lori U.
Sitter Profile Image: Emma & Timothy H.
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Emma & Timothy H.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 28 reviews
10 repeat clients
27 years of experience
Valparaiso, IN, 46385

“Curly loved his stay with Emma & Timothy. It was a last minute reservation so I was grateful to have such accommodating hosts. Communication was awesome. 5/5.”

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Zach L.
Sitter Profile Image: Mianna R.
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Mianna R.
from
$30
per night
10 years of experience
Gary, IN, 46405

About: I have 10 years of experience as a pet owner as well as 3 years of experience as a dog walker / behavior specialist volunteer at a local animal shelter. Over the course of the past five years, I can confidently say I’ve handled over 1,000 dogs of different sizes with ease. Additionally, one of my dogs is a senior with a daily medication regimen, so I know how to pill dogs without any fear tactics. I am also Fear Free Certified! I’m available for boarding throughout most weeks but really open up on the weekends. I am enthusiastic about meeting pups every day of the week! I have a privacy fenced yard and 3 dog friendly dogs to keep your babies company! I am comfortable leaving your pup in a crate if need be, but if not, they can free roam in the dog room (complete with a toddler bed and a tv!).

Sitter Profile Image: Angelique V.
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Angelique V.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 8 reviews
2 repeat clients
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: Shanie J.
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Shanie J.
from
$35
per night
5.0 out of 5 stars
• 253 reviews
75 repeat clients
32 years of experience
Valparaiso, IN, 46383

“Shanie took great care of my pup. Received multiple photos that put a smile on my face. Shanie was extremely flexible when my flight got delayed. I was so grateful. Thank you Shanie for an awesome job.”

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Francia N.
Sitter Profile Image: Lilliana R.
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Lilliana R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 114 reviews
31 repeat clients
8 years of experience
Laporte, IN, 46350

“Lilliana was great and accommodated our change in schedule. Communication was fantastic from start to finish. She also took care of my pet's special needs..it was truly a pleasure to have Peachy in her care.”

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Paulyn H.
Sitter Profile Image: Natasha N.
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Natasha N.
from
$44
per night
4.6 out of 5 stars
• 9 reviews
3 repeat clients
10 years of experience
Michigan City, IN, 46360

“What can I say about Natasha..... we absolutely loved her!!!! This was the 1st time we were away from Denim since we adopted him in May. He's so skittish around new people we were afraid to leave him anywhere. Natasha assured me he'd be in great hands and boy was she right. She spoiled him and loved on him just as we would have. She was available last minute (3hrs before on a holiday weekend) which wad so great. We met at her home and stayed for about 15-20mins until Denim felt comfortable and let her give him belly rubs. She was super patient and didn't mind me checking in on him. She even provided me some photos of him relaxing like he took over her home. I'm super thankful for all she did and would highly recommend her to anyone who needs a trusting person to care for their fur baby. I can't wait to contact her again in the future ??”

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Monai H.
Sitter Profile Image: Dana K.
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Dana K.
from
$50
per night
10 years of experience
Portage, IN, 46368

About: Loving care, plenty of walks, and lots of attention—keeping your dog happy while you’re away. I have taken care of dogs my whole life. I watch my parents dog when they are out of town and also a friend’s two pups when they’re away. As a stay-at-home mom, I’m home most of the day, which allows me to provide consistent care, supervision, and attention to your dog as needed. I will always make sure your dog is on a leash and is safe inside and outside the home. If the dog needs to be in the crate before leaving that will also be done.

Sitter Profile Image: Emmanuela N.
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Emmanuela N.
from
$50
per night
20 years of experience
Fox Park, Hobart, IN, 46342

About: I have a wide range of experience with pets: dogs, cats and rodents of all different personalities, ages and sizes. I will keep your pet happy, fed and toileted! At the moment I work from home, so I’m able to be as flexible as needed around your pets schedule, provided at least 2 days notice In the home the dogs and cats are welcome onto the furniture, with the exception of bedroom and kitchen/dining table. I have a large yard that is fenced in all the way around.

Sitter Profile Image: Sonya M.
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Sonya M.
from
$45
per night
5.0 out of 5 stars
• 25 reviews
7 repeat clients
6 years of experience
Valparaiso, IN, 46385

“Thanks so much for scheduling the meet & greet. And most of all, taking care of my fur baby Zoe. So happy she did so well. Really excited about finding such a great fur mom!! You are so appreciated?❤️ The photos and updates were so very thoughtful and truly beautiful from such a kind soul!”

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Jamie M.
Sitter Profile Image: Angela H.
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Angela H.
Star Sitter
from
$30
per night
4.9 out of 5 stars
• 50 reviews
16 repeat clients
30 years of experience
Hobart, IN, 46342

“What an amazing experience! I always get so nervous having to leave our girls to travel, but Angela was wonderful. She kept them busy, gave them lots of love and sent me TONS of updates and pictures every day of our trip! Right now they are both tuckered out in dreamland because they had such a great time! Thanks again Angela!!”

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Megan F.
Sitter Profile Image: Noel B.
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Noel B.
from
$40
per night
5.0 out of 5 stars
• 36 reviews
17 repeat clients
18 years of experience
Cedar Lake, IN, 46303

“Noel jumped in when I needed a sitter last minute. She took excellent care of Clyde and will continue to use her. She kept me updated and I feel so at peace knowing that she and her family are there for my big guy while my husband heals from his back surgery.”

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Melissa F.
Sitter Profile Image: Laura D.
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Laura D.
Star Sitter
from
$37
per night
4.9 out of 5 stars
• 104 reviews
59 repeat clients
15 years of experience
Lynwood, Lynwood, IL, 60411

“Laura was great with my little Abby. She was flexible with pick up/ drop off times, her home is clean and comfy, took her for a lovely walk to the park nearby and sent update pics. my pup was well taken care of. She even gave her a present to open on xmas and take home! So thoughtful :) will be booking with Laura next time i am out of town.”

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Lauren A.
Sitter Profile Image: Debra & Michael M.
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Debra & Michael M.
from
$35
per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
50 years of experience
DeMotte, IN, 46310

“Debra and Mike are just the best with my little old lady. They play with her and take her on walks. She loves all the snuggles and attention they give her. We will always book with them for our girl. The best for our needs!”

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Abbey S.
Sitter Profile Image: Holly C.
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Holly C.
from
$45
per night
4.9 out of 5 stars
• 18 reviews
6 repeat clients
15 years of experience
Hebron, IN, 46341

“Holly did a fantastic job looking after our dog, Ernie. She gave Ernie lots of attention he needs, and gave us fun and frequent updates. When we need help looking after Ernie again, Holly will be the first person I reach out to!”

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Ryan C.
Sitter Profile Image: Dwight C.
Verified Background Check
Dwight C.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 233 reviews
92 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

“This review is very long over due! Dwight and his wife took exquisite, loving care of my Bentley who typically has anxiety. I have always been so worried about leaving him but not during this long stay. Dwight made Bentley part of family and for that I am grateful. Bentley was happy and healthy upon my return.”

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Juliet K.
Sitter Profile Image: Alisha C.
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Alisha C.
from
$50
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
25 years of experience
Gary, IN, 46403

“Alisha was great with our 7 yr old coonhound, Beau!! Highly recommend. We had a situation where we needed to book an overnight boarding last minute and she was extremely accommodating and helpful. Our pup got along great with her and her pets. We could tell he was very comfortable there. She kept us updated throughout his visit, which is always greatly appreciated. We’ll definitely be rebooking when in the area :) thanks Alisha!!”

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Sarah L.
Sitter Profile Image: Christina K.
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Christina K.
from
$50
per night
20 years of experience
hobart, IN, 46342

About: I've been surrounded by furry friends since day one! 🐶 Seriously, I can't remember a time without a doggo by my side. Thinking about all the pets I've had makes me so happy. 🥰 Anyone else feel like their pets are family? It's the best kind of love! Enjoying the freedom of open schedule currently at home full-time. So furry buddies will get Daily walks around the lake to offer a refreshing escape. Relaxing time outside under tree shade help me do some gardening🤣. Dogs will be created when I am not home. I currently own a golden retriever. She's a friendly dog. I don't have a fenced in yard my dog listens to commands. Leashes and yard leads will be used. At night dogs will be in their creates.

Sitter Profile Image: Ra'eesa S.
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Ra'eesa S.
from
$45
per night
5.0 out of 5 stars
• 24 reviews
9 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

“Ra'eesa kept our doggy while we were out of town. I didn't have to worry about him. He was in good hands with her. She is so nice! She sent pics and videos. Will definitely use her again.”

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Andrea R.
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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
1 / 1
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Chesterton

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Chesterton average 12
repeat dog boarding clients

FAQs for Dog Boarding - Chesterton

Frequently asked questions about Rover

The average cost of Dog Boarding in Chesterton is $44 per night as of November 2026. Most bookings cost between $30 and $52 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 399 sitters on Rover offering Dog Boarding across Chesterton. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

96% of sitters in Chesterton can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

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.

Yes, you can find sitters who have experience with handling special pet needs in Chesterton. On Rover:

  • 88% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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