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!!”
“It was a pleasure having Heather watch our dog for us. We were gone for about 11 days in total. Heather provided daily updates and photos keeping us well informed on how our dog was doing during her stay. We would definitely recommend Heather to others.”
“Sunshine and her kids are amazing! Easy communication and a lot of pictures. Lolla is back home and for the first time she’s not stressed with our absence. I highly recommend Sunshine.”
“Dee was absolutely wonderful with my husky Holly. I felt totally confident that she was safe and well cared for. I was able to relax and enjoy my vacation knowing my dog was in great hands ! I highly recommend Dee !”
“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!”
“Kim provides the best care! Loved seeing pictures and videos to keep us updated. Abby seemed so happy there...I was worried she might not want to leave! Happy to give a 5 star rating.”
“Kim and her family are simply amazing. This was my first time leaving my dog other than overnight (one whole week!) and she did very well. Joey has separation anxiety and has two different medications from the vet to calm her when she’s away from me. I was worried Joey would cry and carry on the whole time, not eat, vomit etc as this is how she experiences stress. Well, Kim knows dogs. She knows how to care for them and put them at ease. Joey did not require medication AT ALL during her stay! She had fun and seemed to bond with Kim quite a bit. When I picked her up, Kim was holding her leash while we talked and I noticed Joey leaning against Kim’s legs at times (this is what she does when she likes someone and feels secure) and, although happy to see me, barely cried. Yes, she cries for everything including joy... Kim was the pack leader and Joey seemed to integrate into Kim’s dog pack very well and the photos showed her enjoying herself. Kim’s dogs are very well-behaved as well. Joey was attacked by another dog last summer so she’s had some social interaction barriers since then, and Kim made sure to carefully and watchfully allow Joey to interact with the dogs at her own pace. I think this healed a large part of Joey’s trauma and allowed her to socialize more confidently and regain trust in her fellow canines, and I have Kim to thank for it. Joey looked so happy and healthy at the end of her stay with Kim and family (dogs tell no lies!) and I will absolutely trust Kim 100% with Joey in the future. Kim, thank you! We can’t wait to see you again!!”
“Veronique took so great care of our Lola, we will definitely want Lola (Boxer Bosten Mix) have Lola in her care again in the future! We received updates woth little clips and pictures as well infos to her dog friends.”
“Jacob was exceptional. He took in our 9 week old puppy Stella for a few days and took incredible care of her. From the initial meet and greet through pickup, he asked great questions, adhered to our requested schedule, gave her lots of exercise and snuggles, all while keeping us in the loop with daily status updates via pics and videos. We felt immediate trust and comfort with him and he did not disappoint. Stella will absolutely see him again soon.”
“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!”
“Rachel was exactly what I needed for my dog. She had open and detailed communication with me the whole time, from booking to pick up. My dog came home happy and healthy. What an incredible weight off while I was out of town to know my girl was well cared for. Would definitely book again.”
“Jennifer was great! We got pics all along of our two pups and could tell they were having a great time & felt right at home, which allowed us to enjoy our trip so much more. Thank you!”
“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!”
“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😊”
“Absolutely awesome! They obviously love animals. My girls had a wonderful time visiting Francine and Bob. This was the first time I left them at a sitter’s house. They sent photos of my girls having fun. That put my mind at ease. I definitely will use them again!”
“Megan was very welcoming and accommodated some last-minute travel plans and made Copper feel right at home. He also got along well with her three pups. He enjoyed having a fenced in backyard where he could run around and play. Thank you!”
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
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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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