Dog Boarding Winthrop Harbor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 30 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.
“Byron and Martha are the best. They took really good care of our dog Noki. They followed up each day with photos and followed all instructions for care. Will be reaching out again for his service thru Rover. For sure a 5 star sitter. Thanks again!”
“We had such a wonderful experience with Heather and Bernie's stay! She was incredibly patient, kind, and caring, and it was clear from the start that she genuinely loves animals. We received plenty of updates and photos throughout his stay, which gave us so much peace of mind. The best sign of all was that Bernie didn't even want to leave when we picked him up! That told us everything we needed to know about how comfortable and happy he was. We would absolutely trust her with Bernie again and highly recommend her to anyone looking for a reliable, loving dog sitter. Thank you so much for taking such great care of our boy!”
“Sunshine took a last minute holiday booking and was incredibly flexible! Always great with updates and photos. Best caregiver for my fur baby that I’ve ever received!!”
“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 !”
“Jennifer spent a week with my puppy while I was out of town, and all I can say is that she is a SAINT! I can’t stress enough how amazing, patient, and kind Jennifer was to Benny. She is great with updates and recommendations. If you need a sitter, you can’t do better than Jennifer.”
“Kim was great with our dachshund. She’s very caring and communicative. She sent photos and updates so we knew our dog was in good hands. Can’t wait to book again when it’s warm for our dog to run around in her fenced backyard!”
“Kim was great! I had a complicated situation after a very stressful week (of moving here from AZ) for my puppy, but felt comfortable leaving him with her. She's experienced with dogs, their behaviors, & training, so it allowed me to not have to worry about him my first day of work here. I am really glad I found her, just knowing that I have a great option for him if I need it relieves a lot of pressure.”
“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😊”
“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.”
“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!”
“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!”
About: Whether your pup enjoys long walks, playtime, belly rubs, or simply relaxing with someone nearby, I’ll make sure they feel comfortable, safe, and loved while you’re away. My goal is to provide a calm, loving environment where your pet receives plenty of attention, affection, and exercise. I am retired so have plenty of time to play with and walk your fur babies as much as needed. I can play with your dog in our fenced in yard or walk them on the Bike Trail, which is just a block away from our home. I’ll tailor my care to each dog’s individual personality and routine. I know how important consistency is, so I’ll follow your feeding schedule, medication instructions, exercise needs, and any special requests. I like to text or email regular photo updates and messages so you can relax knowing they’re having a great time, communication is just as important as great pet care.
“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!”
“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.”
“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!”
“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!”
“Jordan is wonderful! She is so nice to work and I will definitely use her again. Our Luna was super excited to see her after staying with her once before - which is really a comfort when leaving her. Knowing we'll use her again says it all!”
“This was a great fit for our pup. He is an older dog, so not as active. Still loves walks, but very big on rest, relaxing and tons of cuddles. Chisato was great at sending updates, pictures, videos - I could tell he was very well cared for. Will definitely be a repeat customer, assuming schedules on both sides allow for it!”
The median cost per night for dog boarding in Winthrop Harbor is $50
Dog parents share their Rover experiences - Winthrop Harbor
Cynthia was a great fur baby Momma; she loved on Bear more that I could have asked for; she sent updates daily with pictures or video, played with him, daily walks, etc. Five stars is not enough to say the least! Thank you Cynthia for watching Bear while on vacation and making us feel at ease!
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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Popular requests for dog boarding - Winthrop Harbor
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winthrop Harbor average 12 repeat dog boarding clients
FAQs for 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 September 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 September 2026, there are 1,614 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.
92% 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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