Dog Boarding in Winthrop Harbor

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Top rated Winthrop Harbor 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: Tabitha H.
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Tabitha H.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
118 reviews
32 repeat clients
10 years of experience
Kenosha, WI, 53143

Another great stay for our pup, Hazel! Tabitha was able to take Hazel on fairly short notice, and sent pictures every day to show us what a great time Hazel was having!

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Jade C.
Sitter Profile Image: Na Rae & Barry J.
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Na Rae & Barry J.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
9 reviews
2 repeat clients
13 years of experience
Kenosha, WI, 53143

Barry and N.A. Rae were awesome! They kept me updated with pics and videos of my Buddy Boy which put my heart at ease while I was away. I can tell he really enjoyed his stay and I look forward to rebooking with them in the future!

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Lashonda C.
Sitter Profile Image: Jennifer A.
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Jennifer A.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
74 reviews
32 repeat clients
15 years of experience
Waukegan, IL, 60085

Jennifer was AMAZING with our pup Junie! This was the first time we have utilized Rover.com and we were anxious about leaving Junie with someone we didn't know. Jennifer communicated with me weeks in advance and answered all of my questions. Junie immediately felt comfortable and Jennifer texted me pictures and updates throughout the day, which I LOVED. I highly recommend Jennifer to anyone who needs a super responsible and sweet dog-sitter!!

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Zoey Z.
Sitter Profile Image: Sunshine L.
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Sunshine L.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
78 reviews
25 repeat clients
46 years of experience
Kenosha, WI, 53143

Sunshine and her loving family were3 the most amazing host for our young energetic dog, Zuka. She is a big dog and a lot to handle at age 1+. Sunshine is a pro and Zuka loved her time with her. We picked her up a week after dropping her off and she was happy, healthy and maybe it is my imagination... but she also seemed better on her lead! WOW! Above and beyond Sunshine!! Thank You! Thank You! We will always use you for overnights when we travel. D&C

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David G.
Sitter Profile Image: Dee S.
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Dee S.
Star Sitter
from
$60
per night
5.0 out of 5.0 stars
65 reviews
24 repeat clients
60 years of experience
Waukegan, IL, 60085

Dee was amazing! She honestly loves dogs and treated ours as her own while we were away. She sent a steady stream of updates and pictures to keep us in the loop and our dogs and our happiness was her first priority. 11/10, she's an angel and I'd happily have our dog sit with her again.

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Nickolaus C.
Sitter Profile Image: Kim K.
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Kim K.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
72 reviews
30 repeat clients
50 years of experience
Gurnee, IL, 60031

Finn had the besttttt time!! Kim took amazing care of our boy and kept us sooooo updated! I could just tell he had the most amazing time on their walks!! Thank youu so much again!!

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Cassie L.
Sitter Profile Image: Kim F.
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Kim F.
Star Sitter
from
$56
per night
5.0 out of 5.0 stars
494 reviews
207 repeat clients
25 years of experience
Kenosha, WI, 53142

My dog had a blast playing with her dog and family. I appreciated the pictures and video while I was away for the weekend. I have a high energy puppy and her back yard was perfect for running around.

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Natasha S.
Sitter Profile Image: Veronique S.
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Veronique S.
from
$55
per night
4.9 out of 5.0 stars
17 reviews
4 repeat clients
45 years of experience
WAUKEGAN, IL, 60087

I couldn’t be happier, Veronique was a great sitter. My dogs seems very happy and she took very good care of them. She gave them complementally bath before I picked them up. She sent me photos and videos every day to let me know how they were doing and how they interacted with her dogs and cat. Her house, back porch and backyard are really clean, well taken care of and super nice environment for dogs to run free.

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Kenneth P.
Sitter Profile Image: Byron G.
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Byron G.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
14 reviews
5 repeat clients
4 years of experience
Waukegan, IL, 60087

This is the second time we have entrusted Peaches to the care of this wonderful family, and we are just as pleased as the first time—Peaches clearly is as well. We are truly grateful to have found them. Their warmth and attentiveness toward Peaches is remarkable. They are the ideal caregivers anyone could find!!

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Deni R.
Sitter Profile Image: Lucy S.
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Lucy S.
from
$85
per night
5.0 out of 5.0 stars
13 reviews
4 repeat clients
45 years of experience
Winthrop Harbor, IL, 60096

This was our first time using Rover and we were pretty nervous because of some of the stories you hear, but after meeting Lucy we felt completely at ease. She is such a kind and genuine person that we instantly trusted her with our St. Bernard Millie. Millie can be semi reactive around other dogs, so knowing that Lucy has experience with dogs like her really eased our worries. Throughout the stay she kept us updated with photos and videos and made sure Millie was happy, active, and well cared for. We will definitely be using her again and highly recommend her to anyone looking for a reliable and attentive sitter.

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Chris K.
Sitter Profile Image: Nicholaus G.
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Nicholaus G.
from
$65
per night
5.0 out of 5.0 stars
4 reviews
2 repeat clients
20 years of experience
Zion, IL, 60099

Nicholaus G. took great care of our two dogs while we were on vacation. He provided updates throughout our trip which helped us feel at ease with leaving them with someone new.

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Lisa L.
Sitter Profile Image: Brianna E.
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Brianna E.
Star Sitter
from
$51
per night
5.0 out of 5.0 stars
325 reviews
48 repeat clients
8 years of experience
Kenosha, WI, 53143

I can’t say enough good things about Brianna!! I have a very nervous, skiddish almost 2 year old puppy, and after the first night, he was completely comfortable due to Brianna being so patient and understanding with anything he needed to feel safe. I got daily updates and photos, quick responses, and felt completely at ease while on vacation that my puppy was getting the best care in Brianna and her family’s hands!

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Sarah R.
Sitter Profile Image: Connie S.
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Connie S.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
41 reviews
11 repeat clients
35 years of experience
Bristol, WI, 53104

My dog Flash stayed at Connie’s for 17 days during my trip overseas. I had never used Rover site + Flash never stayed with someone he did not know for such a long time, but they got along very well ? Connie kept me updated often with videos, photos and detailed report about how Flash was spending his day with them. Even though Flash can’t talk, I can tell he loved the walks, rolling in the grass in their large backyard, playing fetch forever, playing with challenging puzzles, cuddling on their sofas, sneaking upstairs to check their son’s bedroom for a quick nap..) It was very assuring and I could concentrate on my travel without worrying about Flash. Communication was fast, arranging times for meet/greet, drop off/pick up were super easy and accommodating. I would definitely board Flash again for my future travels.

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MIKA N.
Sitter Profile Image: Michelle S.
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Michelle S.
from
$25
per night
5.0 out of 5.0 stars
7 reviews
1 repeat client
10 years of experience
Zion, IL, 60099

About: I am a 30 year old female who loves all animals. I have grown up with animals all my life and have owned many of my own pets. I very much like spending time walking around or just sitting and gaming and cuddling with my pets. I am able to train puppies as i have owned a 3 time grand champion vizsla, though I am no professional I was just taught so i could show my dog. I enjoy spending time in the woods and or in the ocean just being about in the beauty of nature. I hope and pray to be able to meet your little or big angel because that is what a pet is an ANGEL and a beloved family member. please enjoy your day! it is my life. i do this for my job, but i do love all animals so i am more than happy to do this. im very patient and willing to just let them get to know me. i follow things to a tee that way your pet gets the care it needs

Sitter Profile Image: Chisato A.
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Chisato A.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
64 reviews
16 repeat clients
20 years of experience
Gurnee, IL, 60031

Chisato was exceptional with caring for our Lexxie. We made the best decision ever for the care of our dog. For seventeen days Chisato would take time to send photos and videos of our dogs activities. They were quite humorous and lovable. Lexxie was safe and adjusted quickly. All of our dogs needs were met along with her medicine, feedings, play time, and those walks during the freeze for several days. If anyone desires to have a reliable committed dog boarder, I totally recommend Chisato 100%!!!❤️

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Leslie A.
Sitter Profile Image: Jordan G.
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Jordan G.
from
$40
per night
5.0 out of 5.0 stars
14 reviews
4 repeat clients
10 years of experience
Gurnee, IL, 60031

Jordan was great! Was our first time in Rover but Jordan put us at ease and provided regular updates with video and pics, and texted often. She took great care of our Clark and I recommend Jordan highly!

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Harvey H.
Sitter Profile Image: Jacob Miles F.
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Jacob Miles F.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
101 reviews
34 repeat clients
10 years of experience
Grayslake, IL, 60030

Jacob was great! He took good care of Muffin, was always responsive and available, and was very flexible with the pick up and drop off times. Thank you for watching Muffin while we were on vacation!

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Caroline M.
Sitter Profile Image: Swagata H.
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Swagata H.
Star Sitter
from
$55
per night
5.0 out of 5.0 stars
18 reviews
5 repeat clients
9 years of experience
Waukegan, IL, 60085

I had an amazing experience with my pet sitter! She took excellent care of my two kittens, Panther and Mochi, and made sure they were always happy and entertained. I loved how much she played with them and kept them active. One of my favorite parts was receiving videos and pictures throughout the time she had them. It gave me so much peace of mind. She was truly an excellent caregiver, and I would definitely bring them back to her in the future whenever needed! Thanks so much!!!

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Steph N.
Sitter Profile Image: Mary & Norman B.
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Mary & Norman B.
Star Sitter
from
$60
per night
4.9 out of 5.0 stars
30 reviews
4 repeat clients
30 years of experience
Gurnee, IL, 60031

Mary and Norm welcomed Bambi in as part of the family and I could tell from the photos it took her no time at all to adjust to her new surroundings. She can't wait to stay with them again.

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Jessica S.
Sitter Profile Image: Samantha J.
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Samantha J.
from
$60
per night
5.0 out of 5.0 stars
4 reviews
2 years of experience
Waukegan, IL, 60085

About: I have 2 years of professional dog/cat handling. I currently work at an animal hospital as a kennel attendant! I have had dogs of my own growing up, and now I own 6 cats. I just love caring for animals. I am free Monday-Friday so I will be available to give all my attention to your fur baby! They will have plenty of cuddles and play time! My mom and I will both be very much involved with your fur baby! I do not have a fenced yard BUT I will gladly take your doggy on multiple walks! I do have 6 cats but they have their own room/space so they will not interfere with any animals I’m boarding :)

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Over 69
pet parents in Winthrop Harbor have booked dog boarding

Winthrop Harbor dog parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

Nice to have people like Nicholaus, Kai was nice with him, calm and loved. I was worried because it was a lot of time out of the city but I saw he was good from the first day. If you need someone to take care of your dog he is your best option.

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Juan Carlos M.
Boarding
5.0 out of 5.0 stars

Nicholaus G. took great care of our two dogs while we were on vacation. He provided updates throughout our trip which helped us feel at ease with leaving them with someone new.

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Lisa L.
Boarding
5.0 out of 5.0 stars

Lucy took great care of our big buddy Arney. Her home felt like home. She sent lots of pictures and videos with summaries of how their day went. She treated him like family and could not have asked for a better dog sitter. Best dog mom ever!

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Natalia B.
Boarding
5.0 out of 5.0 stars

Lucy does a great job with our doggies. She seems to really enjoy them. She kept me updated daily with pics and comments. I know my pups are in good hands with Lucy and I can enjoy a trip knowing that.

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Patti B.
Boarding
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Winthrop Harbor is $50

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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

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

Sitters in Winthrop Harbor average 12
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jan 2026, the median cost of dog boarding in Winthrop Harbor is $50 per night, including service fees. Boarding your dog for one week typically costs $350. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winthrop Harbor dog boarding rates can be found as low as $21 to as high as $66 per night.

If you’re searching for a Winthrop Harbor 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 Jan 2026, 626 sitters provided dog boarding in Winthrop Harbor. 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, 94% of Winthrop Harbor dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Winthrop Harbor have an average of 19 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 Winthrop Harbor.

Rover makes it easy to find Winthrop Harbor 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 626 dog boarding sitters in Winthrop Harbor on Rover, so you’re sure to find the perfect match for your dog! In Winthrop Harbor, 90% of sitters offer daily exercise, 95% offer medication administration, and 87% 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.