Dog Boarding in Winthrop Harbor
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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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.
“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!”

“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!”

“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!!”

“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”


“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.”

“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!!”

“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.”

“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.”

“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!!”

“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.”

“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!”

“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.”

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
“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%!!!❤️”

“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!”

“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!”

“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!!!”

“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.”

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 :)
Over 69 pet parents in Winthrop Harbor have booked dog boarding
Winthrop Harbor dog parents share their Rover experiences
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Select a filter and find qualifying Winthrop Harbor sitters!How Rover works

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. 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. Book & Pay
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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.
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.



