Dog Boarding Winnetka
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Winnetka, 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.
“Kazuhiro and Akemi were simply fantastic with Regina George! She is a bit timid but was very comfortable with them and their other sweet dog guests. You could see how calm and relaxed all dogs were and that seemed to immediately make Regina George calm as well. While she was a touch nervous during her stay they provided constant updates and pictures. We were completely relaxed and secure knowing she was being taken care of. You could tell they were true dog lovers! Highly recommended for others. Looking forward to her next visit with them!”
“We definitely recommend Diane! She is warm, inviting and sensitive to our dog's needs. She kept in touch with us to let us know that all was going well. It is obvious that she cares for dogs a great deal!”
“Jeff and Ron took care of our standard, 4 1/2 year old Bernedoodle. It was our first time leaving her and we were cautious in who we chose to care for her. Jeff. And Ron lived up to their highly rated reviews! We set up a meet and greet and also decided to have our pup spend a day with them before leaving on our 4 day getaway. Jeff’s friendly demeanor with us and our pup put our minds at ease. We felt comfortable knowing our dog was in good hands!”
“Took great care of my little kitty and let her be part of her lovely family. Very communicative & helpful as a first time rover user! She was also super flexible in terms of last minute booking, pickup times, etc.”
“Rico and his family are great. They always take excellent care of Rye, and this past weekend was no exception. Rye came to them with some stomach issues, but they were still willing to watch him and took such great care of him! He loves being at their home.”
“Karla did a great job taking care of our dog, Lucky. We’ve only had Lucky for a few months, and as a rescue from Texas, he has a lot of separation anxiety. Karla was very understanding and made him feel relaxed and at home, while also being patient with all of his little foibles. She sent us lots of pictures and videos, which we really appreciated. She also has a great setup for dogs, including a large long condo with plenty of space for running around. We would definitely recommend Karla to others!”
“Rizwan, Noorjahan and their family were such great sitters for our dog and cat! They are such a sweet family and we received many pictures every day. I was reassured that both my pets were having a great time with them! Will definitely reach out again for our next sitting.”
“Rebeca did an outstanding job with our nervous puppy. She was very patient with his puppy energy even as our dog unfortunately was not very well behaved. Rebeca did a great job keeping us up to date on everything going on and sent us lots of pictures. I would highly recommend for anyone needing dog watching services.”
“Diane was amazing. I have two small Maltese dogs with separation anxiety, so I was very nervous about leaving them. From the moment we met, she made me feel at ease. She welcomed them into her home and went above and beyond to make sure they felt comfortable, safe, and confident. It was a wonderful experience, and I could tell my dogs were happy and well cared for. I’m already booking with her again for future stays. Highly recommend!”
“Sarah was SO GREAT with our two little dogs!!! She sent pictures and videos every day while we were away, and little notes about how they were doing- the good and the bad, when one of our dogs decided that her plant was a perfect place to sit. :) THANK YOU SARAH and we look forward to trusting you with our little ones again when we need you!!!”
“He provided multiple updates and pictures. My dog was not only super excited to meet him, but looked happy and well taken care of in the pictures I got. I trust my dog was in great hands, and I'll definitely be booking with him again!”
“Undram did an amazing job caring for Gizmo. He came home to us so happy and calm. I can tell he was well loved and understood. We were so thrilled after a grueling flight to come home to such a happy pup!”
“Abigail and her family are true gems. My girl is 13 years old and typically very anxious. She is so comfortable with the family. I wish I had found Abigail and her family years ago ❤️”
“I highly recommend Olga for her pet sitting services. She took amazing care of our dog, Zoey. She played with her and took Zoey on a lot of walks (which she loves). Her communication was great- she sent daily video and photo updates which gave us peace of mind… Zoey looked like she was having the best time. We can’t wait to have Olga watch Zoey again!”
The median cost per night for dog boarding in Winnetka is $50
Dog parents share their Rover experiences - Winnetka
Our dog absolutely loved his stay with Andrea and her family. We are a couple days out from him returning and he seems like he’s still missing his time there. You can tell Andrea and her kids care for the dogs. They have a secure fenced in backyard and it seems like our dog got to enjoy some time outdoors. We loved the updates and cute pictures she sent. We will use her again in the future. Thank you!
Ella is the best! She was incredibly attentive to our dog’s needs and made sure to send us plenty of photos of him having a blast while we were away. It was a huge relief for us (and our nervous pup) to leave him with her instead of a boarding facility. We can’t recommend her more!!
We used to leave our dog at a large dog boarding place when traveling, and she would be grouped with so many different dogs that I can tell she was traumatized and often took days to be back to her normal carefree self (and she would have dog drooling all over her). This time under Nancyanne’s care our dog was able to stick to a routine similar to at home, and I can tell she was quite comfortable and after 9 days it was seamless that her demeanor was like she never left home. We would happily recommend Nancyanne to anyone who needs help.
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 - Winnetka
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winnetka average 10 repeat dog boarding clients
FAQs for Dog Boarding - Winnetka
Frequently asked questions about Rover
As of October 2026, there are 4,964 sitters on Rover offering Dog Boarding across Winnetka. 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.
95% of sitters in Winnetka 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 Winnetka 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 Winnetka.
<b>Tip:</b> 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 Winnetka 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.
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