Dog Boarding Winthrop Harbor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 29 pet parents in Winthrop Harbor have booked dog boarding
Winthrop Harbor, 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.
“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!!”
“Heather was absolutely amazing with our dog, Arlo, while we were out of state for a funeral. Leaving him was incredibly difficult for us because we had never left him before, but Heather gave us peace of mind from the very beginning. She reassured us many times before and during our trip, which meant so much during such a hard time. She sent multiple pictures every single day along with detailed updates, and it was clear Arlo was being treated like part of the family. Heather and her family took such wonderful care of him, and we could truly see how loved and comfortable he was while we were away. We honestly could not have asked for a better experience. Heather made a painful and stressful time so much easier for us, and we are beyond grateful we found her. We would give her 10 stars if we could and highly recommend her to anyone looking for someone trustworthy, caring, and compassionate to watch their pet.”
“I appreciate Jennifer’s help so very much. She treated Tony the dog so very well and even let me know how he was doing day to day. She really helped us both out so very much and I hope to get her help in the future!”
“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 IS AN ANGEL! My mini poodle is an anxious/reactive dog so it’s hard to find people who are willing to watching him and understand his quirky behaviors. From the initial meet and greet, it was obvious how much Dee loves animals and dog sitting. I left my dog with her for 5 nights and couldn’t be happier with how comfortable he was with her. Dee provided multiple daily updates with pictures and videos, and she kept up with his 3 time a day feeding and his daily meds. It’s great to know that there is someone like Dee who will care for my baby like I would. Thank you so much!!!”
“Kim and her family took great care of our puppy, Mojo. It was his first time away from us and he came home happy and clean after a week of play. We especially enjoyed the photos of Mojo that Kim provided as it gave us an idea of his day. Thank you, Kim!”
“Kim is always great with our little dog Winston. She provided walks, a large yard for him to run around in, and lots of pictures and updates. Winston loves being spoiled there.”
About: I am a vet tech at Kenosha Lakeshore Vet and my everyday life consists of interacting and taking care of dogs and cats in need❤️ I am currently not working a job at all so i am free 24/7 to watch/walk your animals anyday anytime!! thank you for booking with me!🙂 I have no animals in my home so there is no worries there and I will take care of your animals with your needed instructions. I am also very capable of walking a bigger dog and know how to well take care and play with your animals as I am a vet tech and do that on my day to day basis.
“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.”
“Keira & her boyfriend were so sweet to my dog. She loved staying with them & was so tired when she got home. They sent me so many photos & updates. Would definitely recommend & rebook!”
“Rachel was absolutely wonderful with Dottie. Being new to the area and having to travel for business, I was very nervous finding a new sitter as Dottie has some extra needs in her older age. I appreciate Rachel’s updates and willingness to help in a time of need. Thanks again, Rachel!”
“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.”
“Alyssa is amazing. She LOVES pups and takes care of them like they were her own. She cuddles them, plays with them, walks them, and does whatever you ask her to do. She is a delight to deal with, so positive and loving. I received photos, videos and puppy updates periodically every day. I highly recommend Alyssa. You’d be lucky to have her caring for your pup!”
“I can’t say enough good things about Jennifer! She took wonderful care of my dog, treating them like family. I received regular updates and photos, which gave me peace of mind while I was away. My pup came home happy, relaxed, and clearly well-loved. It’s hard to find someone you can truly trust with your fur baby, but Jennifer went above and beyond. I will definitely be booking again and highly recommend her to anyone looking for a reliable and caring dog sitter!”
“We are extremely happy with our dog's stay at Jennifer's house. Jennifer treated our doggie as her own and we received a lot of pictures and updates. I would definitely recommend her!”
“We wanted to express our sincere appreciation for your exceptional care of my anxious dog while we were on vacation. It was a relief knowing you kept him comfortable and safe, especially with his anxiety. We also really appreciated you keeping him separate from your cat due to my daughter's allergies – it showed a real dedication to his well-being and consideration for my family. The updates and photos you sent were so reassuring. Thanks again for going above and beyond! Will definitely take Cody back on our next vacation😊”
“We only needed to book one night with Christy, but she still sent an update with a pic...and took our Temo for a little car ride! We appreciated her flexibility with drop-off/pick-up. We would recommend her, and would utilize her services again.”
“Once again Veronique has exceeded my expectations. Was my second time having her watch my dog Jimmie. She is wonderful and she has demonstrated her passion and expertise for canine care, by taking excellent care of my dog, and by sending me numerous photos and videos of Jimmie during her many long walks in parks and forest perserves which my dog loves. I did not worry a bit with Veronique in charge. Jimmie had a super great time playing with her two dogs. I highly recommend her for dog sitting and grooming.”
“Melissa did an amazing job boarding my cats over the Christmas holidays. Timely updates and cuddles were provided to me and my cats respectively. Highly recommend & appreciated.”
The median cost per night for dog boarding in Winthrop Harbor is $50
Dog parents share their Rover experiences - Winthrop Harbor
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.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog boarding
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests near you
Select a filter and find qualifying Winthrop Harbor sitters!Sitters in Winthrop Harbor average 12 repeat dog boarding clients
FAQs for Dog Boarding - Winthrop Harbor
Frequently asked questions about Rover
The average cost for Dog Boarding in Winthrop Harbor on Rover is $67.71 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 1,660 sitters on Rover offering Dog Boarding across Winthrop Harbor. 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.
93% of Winthrop Harbor 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 Winthrop Harbor 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 Winthrop Harbor 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 Winthrop Harbor.
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 Winthrop Harbor 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 IL 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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