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

Over 32 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!”


“My 6-yo German Shepherd had a wonderful time at Dee's place! My dog, who is a rescue and doesn't do very well at pet hotels (she always gets stressed out and gets diarrhea) didn't have any health issues after I picked her up from Dee's house. Dee is amazing - she takes care of your dog with such love and care, as if they are her own! I'd definitely go back to Dee next time we need a sitter and she's available!”

“Kim was prompt, punctual and really likes my puppies. Her fenced yard worked really well with my 2 puppies. They even have a German short hair puppy as a playmate! Glad we found Kim in Rover!”

“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.”

“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😊”


“Kelly, along with her own pooch Maggie, were excellent companions for our puppy's first stay away from home. Kelly was on top of everything, because she's very professional and caring. I really appreciated the photos she sent each day showing that our dog was having a good time. Kelly was always on top of the entire process. Because we were traveling to and from the airport, together we made the drop off and pick up as smooth and quick as possible. Kelly's location, about five minutes from the airport, was perfect too.”

“This was my first time using Rover and am very happy with the experience. Megan was very responsive and provided daily updates. I felt comfortable leaving my dog at her house and would definitely book with her again.”

“They were absolutely amazing! I was nervous to leave my dog because he is big and has a lot of energy but he did such a good job, and they stayed in constant communication with me and sent me pictures which eased my nervousness! They are super friendly and love dogs!”

“Wow, I was very happy with my dog Riri's overall stay. This was my first time using Rover.com, I was a little worried but I am so glad I did. Riri is a rescue, she has separation anxiety. Taking Riri to Aesia's home, she look comfortable and relax, this is rare for her. I am so happy that Aesia enjoyed Riri as well. My husband is in the military, this service is prefect for us because we are new to the area and and it's nice to know we already found someone that Riri feels comfortable staying with if we need a sitter. ”

About: Hi there! My name is Jamie and I am a very active dog lover!! I love taking dogs for walks and runs, playing fetch, playing tug-of-war, and playing any other kinds of games that your dog may enjoy! I have 3 years of paid experience in caring for both dogs and cats. I love spending time with furry friends and will make sure that I take care of your pet as if it were my own! My husband and I have two English Cream Retrievers and we love them more than anything in the world! I know that puppies, dogs, and all other animals require a lot of time and attention, and I am more than willing to provide the care that they need! My husband and I are both Firefighter/Paramedics, and know first-hand how difficult and anxiety provoking finding a reliable pet sitter can be. I am committed to walking your furry friend when needed, dropping in to visit them while you are away for the day, and we are open to hosting your furry friend in our home if you need extended care. We have a small, fenced in backyard where your furry friends can play with ours, and we live near the lake so extended walks are always available!! I look forward to hearing from you and meeting you and your fur-babies!! I am a Firefighter/Paramedic and work a rotating schedule. I know my schedule in advance, so scheduling should not be an issue! If we are boarding your dog in our home, someone is almost always home between my husband and I! We also walk our own dogs daily, so we are used to daily walks and exercise! If your fur-baby is spending time at my house, I have two very loving and playful doggos that can keep your dog company! I live near the lake, so there are plenty of places to walk and explore! I am also willing to take your dog to the dog park at Pets Park if that is something your dog would like! I am very active, so long walks/runs are not an issue!
“Valeria is a wonderful dog sitter! She picked up my dog from my cousin’s house nearby and had him while we were traveling overseas. She sent photos of him inside, on walks, and playing. At least 3 a day. She had very specific questions about him and asked permission for types of treats. She was always available to message back and forth about my dog and was very clear about how he spent his days. My dog looked very happy and very well cared-for at her house. I definitely recommend Valeria and will absolutely re-book with her!”

“Jean was amazing with my golden. I loved getting pictures and videos daily and knowing that he was having a great time. My big guy has terrible anxiety during storms and is on a high dose of anxiety medication that sometimes works. When a bad storm rolled in Jean was compassionate and loving and notified me about his condition. As a very overprotective dog mom I trust Jean and we will definitely be using her again.”
“Tracy is so kind and caring!! She made sure my dog was safe and had lots of fun! She was quick and detailed with her communication. I will definitely be booking with her again in the future!!”


“Elizabeth is an amazing person and Rover care provider, she is very professional. She responded quickly and I was able to go on my emergency. Her home safe and friendly, Jack felt good in home. she sent us a lot of pictures and videos of Jack. Jack has been well care for. I am definitely bringing Jack back to Elizabeth’s home. Thank you.”

“Jessica is fantastic! She took our pup to the park and on her errands which made him very happy. Very communicative too the entire time with photos and videos. And she takes excellent photos to boot!”

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.
How to book dog boarding

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
It's that easy! All payments are processed through Rover's secured platform.
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 Dog Boarding - Winthrop Harbor
Frequently asked questions about Rover
The average cost of Dog Boarding in Winthrop Harbor is $68 per night as of October 2026. Most bookings cost between $34 and $101 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 1,593 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 routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
94% of sitters in Winthrop Harbor can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winthrop Harbor home-away-from-home, 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 , 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 .
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.








