Dog Boarding in Chesterton

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Top rated Chesterton dog boarders

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: Jordan C.
Verified Background Check
Jordan C.
Star Sitter
from
$50
per night
4.9 out of 5 stars
292 reviews
126 repeat clients
12 years of experience
Portage, IN, 46368

Jordan was very accommodating. We ran into several obstacles coming home from our trip and were late picking up our dog. Jordan was very understanding and we are thankful for her patience. Our dog warmed up to her family, and got along with everyone there. We're hoping to use Jordan again within the next few weeks for our vacation. :)

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

This is my first time using Rover or any pet service. We met Cathy with my dog Jenni ahead of her stay-over which made it a familiar experience when she went for boarding. Cathy is very caring and great with animals and I have already scheduled another stay for my dog with her for a work trip. Thank you!

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Karen H.
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
104 reviews
51 repeat clients
8 years of experience
GRIFFITH, IN, 46319

Joy and Dan are great! Within minutes of dropping Tabi off I received pictures. What a wonderful family. They will always be my go-to because of all the love and attention Tabi received while staying there. Thanks again!

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Gina C.
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
57 reviews
31 repeat clients
45 years of experience
MICHIGAN CITY, IN, 46360

This was our first time using Rover for one of our dogs so I was a little nervous. Janis sent pictures of our dog every day while we were gone. I felt very comfortable leaving Remy in her care. Our pup seemed happy and well taken care of. I would definitely recommend her to someone and will be reaching out again if we ever need a sitter. Thanks, Janis!

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Rachel P.
Sitter Profile Image: Shanie J.
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Shanie J.
from
$35
per night
5.0 out of 5 stars
240 reviews
72 repeat clients
32 years of experience
Valparaiso, IN, 46383

Shanie's dog boarding for my puppy for 2 weeks deserves the highest rating --she sent little reports and photos and videos at least 2x/day which I loved and my puppy loved her home, expansive outdoor area, and all the toys and treats. It was hard for me to leave my puppy but Shanie made it easier and when we need another dog boarder I hope we get Ms. Shanie!!

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Valerie W.
Sitter Profile Image: Giannina G.
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Giannina G.
from
$30
per night
4.9 out of 5 stars
90 reviews
38 repeat clients
5 years of experience
Miller Beach, IN, 46403

This App and the service Giannina provided for Mason was amazing. I can tell he felt like he had a second home in her care. We will definitely be using her boarding again. Ruff Ruff Mason approves

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

Meredith did a great job with my two girls! I was a little concerned at first, not sure if she could handle my 10 month old German Shepherd, Jream, but overall, she did very well even without having a fenced yard. My girls still got a full hour of playtime in a nearby fenced area where they were able to run and play ball freely. Meredith followed all my instructions, and I would definitely use her again.

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Alvia G.
Sitter Profile Image: April Y.
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April Y.
from
$56
per night
5.0 out of 5 stars
44 reviews
13 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: Mary S.
Verified Background Check
Mary S.
from
$40
per night
4.9 out of 5 stars
235 reviews
80 repeat clients
20 years of experience
Michigan City, IN, 46360

Mary did such a great job taking care of my pup for the weekend. She sent a very thorough questionnaire to make sure she knew everything important about caring for him. Would recommend!

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Alison E.
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

We are so happy to have found Nancy and Mark. Our dog has stayed with them for 2 extended visits and has been well cared for. Our dog is quite anxious and not a good walker so having a small fenced in area to let her out is great. Nancy is very communicative during the stay and sends photo updates. We will continue to use for sure!

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Heather K.
Sitter Profile Image: Cassidy M.
Verified Enhanced Background Check
Cassidy M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
143 reviews
51 repeat clients
8 years of experience
Highland, IN, 46322

Cassidy and her family took really great care of Belle. I was so nervous because I have never used rover before. Cassidy took the time to check in and send little updates about Belle and pictures. It eased my mind a whole lot and I was able to enjoy my getaway knowing my dog was in great hands. I will definitely be using her services again.

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Antonia B.
Sitter Profile Image: MacKenzie T.
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MacKenzie T.
from
$55
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
15 years of experience
Burns Harbor, IN, 46304

She was awesome!! Took great care of our doggy, she even picked him up... it was a long term stay, he seems happy, we definitely recommend Mackenzie and will be using her services in the future!!🙂👍

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Om V.
Sitter Profile Image: Monica & Joseph L.
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Monica & Joseph L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
88 reviews
41 repeat clients
26 years of experience
Cedar Lake, IN, 46303

Monica and Joseph are absolutely wonderful— they treat my toy poodle, Dash, like family. I always have complete peace of mind knowing he’s in their care. They send daily updates and photos, which I truly appreciate. I can’t recommend them enough—don’t hesitate to book with them! 🐾✨

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Tonya S.
Sitter Profile Image: Jesseeka & John G.
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Jesseeka & John G.
from
$45
per night
4.9 out of 5 stars
75 reviews
14 repeat clients
20 years of experience
Merrillville, IN, 46410

Jess is amazing lady came home all worn out from all the fun she had ! She’s very accommodating she checks in with pictures and updates throughout the stay ! I can tell she really loves what she do…. I will be booking with her again 😊 Thanks again ☺️

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Normeisha S.
Sitter Profile Image: Bernice S.
Verified Enhanced Background Check
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

Thank you Bernice for being so sweet to my little Peach! It was a really enjoyable experience from start to finish. Bernice communicated well and helped ease the transition to her care. We were able to book, meet up, and confirm the boarding within the week. I knew it was a good sign, when Peach started alerting us as we pulled up to Bernice's home. Peach seemed pretty excited to be back. During Peach's stay Bernice sent great pics. It was apparent that Peach had a great time in Bernice's big back yard and made good friends with Bernice's dog. I really appreciate the time and patience! Thank you again.

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Yury F.
Sitter Profile Image: Javier & Andrea A.
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Javier & Andrea A.
from
$35
per night
4.5 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Merrillville, IN, 46410

You guys were excellent thank you thank you thank you for taking wonderful care of my baby. I love all of the pictures and the videos will definitely use you guys in the future.

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Cassandra F.
Sitter Profile Image: Amia Mona & Joshua P.
Verified Enhanced Background Check
Amia Mona & Joshua P.
Star Sitter
from
$35
per night
5.0 out of 5 stars
6 reviews
5 repeat clients
14 years of experience
Lansing, IL, 60438

Amia,Joshua and family have been nothing but great to my baby Barry. He loves spending time over there, I definitely recommend them. They are the best fit for your fur baby 🙂

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Juanita T.
Sitter Profile Image: Madelyn O.
Verified Background Check
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.
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Over 173
pet parents in Chesterton have booked dog boarding

Chesterton dog parents share their Rover experiences

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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The median cost per night for dog boarding in Chesterton is $43

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  • Reservation protection

    It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

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    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Chesterton average 12
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Chesterton is $43 per night, including service fees. Boarding your dog for one week typically costs $301. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chesterton dog boarding rates can be found as low as $22 to as high as $61 per night.

If you’re searching for a Chesterton dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 123 sitters provided dog boarding in Chesterton. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 87% of Chesterton dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Chesterton have an average of 24 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Chesterton.

Rover makes it easy to find Chesterton dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 123 dog boarding sitters in Chesterton on Rover, so you’re sure to find the perfect match for your dog! In Chesterton, 92% of sitters offer daily exercise, 100% offer medication administration, and 92% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.