Dog Boarding In Winnetka
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Feel secure with ID-verified sitters and 25.000 € in eligible vet care. Learn about RoverProtect
Top rated Winnetka dog boarders
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 15%.
“Armando was very quick to respond and did a great job with our puppy Haku! We could tell Haku had a great time and was very calm and comfortable in Armando’s presence. Armando’s yard is also very well kept and spacious. We will definitely book again!”
“Our dogs stayed with Annabelle & Ben for one night as a trial before our longer, upcoming trip. Everything went really smoothly and we appreciated their communication with frequent updates and pictures on how they were doing.”
“This was our second visit. Alexis and Melissa are wonderful caregivers! Gunner can be very anxious in new environments and not only was he relaxed but he was very happy on his visits. Alexis and Melissa send updates and photos throughout the day and certainly keep us notified about anything going on. We will certainly return.”
“Marcella is awesome she is a very caring and nurturing individual! She is really great with animals. I will definitely be using her in the future for all my animals! Thank you so much Marcella! 😊”
“I had to take a trip and all my family members were not available. This was my first time using Rover or any other dog-sitting app. I was very fortunate to find someone that I felt very comfortable leaving my older German Shepherd with. Patricia's personal experience with her own pets made me very comfortable in trusting Tyson with Patricia. We met to introduce our dogs and everything from there was smooth sailing. Patricia was fantastic in keeping me up to date with everything and she sent pictures throughout the process. I feel like I now have someone I can count on to care for my dog when I am not available. And that is a great feeling to have!! Patricia is great!”
“Here's a revised version of your text with some adjustments for clarity and flow: Kiyarash did a great job watching my dog, Oreo. When I picked him up, he was calm and happy to see me, which assured me he had been in good hands. The last time I had a sitter, Oreo returned very jumpy and shaky. However, Kiyarash really took care of him, and I will definitely be rebooking him again.”
“Renata was absolutely amazing with our little pup! She kept us updated throughout the day with photos and videos. Biggie looked like he was having the time of his life and came back happy and chill. Would absolutely hire Renata again and I plan to! ❤️”
“Monica was fabulous with our Wolfie! She checked in often and I could tell he looked so happy and comfortable in her home. I would definitely recommend her to anyone!”
“Rachel and Preston were amazing dog sitters! They texted me daily updates, which gave me so much peace of mind while I was away. During the stay, my one-year-old dog and their dog became best friends, and it was clear my dog was having the best time and receiving lots of love and attention. I feel so lucky to have found the best care for my dog, and I will definitely use their services again!”
“Thank you, Thank you, Thank you. Sonia, you were more than a special dog sitter, you were like a special auntie. I could tell by all the photos you sent me, that you made her feel so comfortable & safe in your home. You made sure she felt protected & loved & i really appreciate that. I will recommend you to anyone looking for a sitter & I will Bring Misty back to you again. Thank you again.”
“Wonderful experience. Both my pups had a great time. Recieved lots of pics, great communication, and they were sent home with some stuffies to remember their time with Ko. Would be happy to rebook :) Thank you Joseph!”
“A very thoughtful and kind couple who took great care of our small dog for nearly two weeks. They sent regular updates throughout our trip, which really put us at ease. We wouldn’t hesitate to book with them again.”
“Hayley and Arthur are very dedicated, professional and above all, they really love dogs! They understand animals and their needs. They have 2 dogs of their own and they were very attentive to properly introduce them to our pups. Beside having access to a large, safe backyard, our pups were taken for walks and offered plenty of attention. Hayley was so kind to take the time to send us daily updates as well as pictures and videos. It was so obvious that both Vanilla and Riley, our pups, were having a blast in their home! We are grateful to have found them, and we highly recommend their services.❤️”
“This was the first time using this app to get someone to watch our dog while we are away and I’m very happy with the app and our dog sitter Susan. I felt very comfortable leaving our puppy with her. While away, Susan updated me how our puppy was doing and sent me pictures. Our puppy seemed so happy and playful. I know I’ll be using the app for our future dog sitting services and definitely we’ll request Susan to watch our puppy. Thank you Susan so much for taking good care of our puppy.”
“Love the attention Phil and Lauren gave Bailey. Taking her for walks, giving her treats and scratching her butt like she enjoys. They treated her like she was part of their family. Texting me photos of her off and on during her stay which made me feel comfortable. I will definitely use them again.”
“Newman had a wonderful stay with Ryan and Abbey. He came back home comfortable and calm. Ryan also made sure that he ate, stayed hydrated and got timely breaks to go outside. Ryan communicated well and sent us photos and videos along the way. Thank you!”
Over 875 pet parents in Winnetka have booked dog boarding
Winnetka dog parents share their Rover experiences
Louella took care of my 8-month-old puppy for 9 days, and I could not be more grateful for the level of love, attention, and professionalism she showed. From the moment I dropped him off, I felt completely at ease knowing he was in the best hands. She sent daily updates with photos, videos, and texts showing how happy, relaxed, and well cared for he was. It was clear he felt right at home with her. Seeing him play, cuddle, and explore with that big puppy smile made the time apart so much easier. Louella treated my pup as if he were her own, and that kind of care is rare. When I picked him up, he was his joyful self, and it was obvious he had an amazing time. I highly recommend Louella to anyone looking for someone trustworthy, attentive, and genuinely loving. She is a true gem, and I will gladly book with her again.
Mariia, & her family were amazing! We couldn’t have asked for a better dog sitter! She took amazing care of both of our dogs, communicating every day with pictures and how they were making themselves at home:) especially being knowledgeable with having a senior dog out Max. (16yrs old) Knowing they were in such caring hands gave us complete peace of mind. We came home to two happy pups and are so grateful. We highly recommend her!
My rescue Charlie is by my side wherever I go and I get a bit nervous when I leave her with anyone else. However, Janiece made Charlie feel right at home and you can tell she is truly a dog lover. Charlie was free to roam her home and yard and this was important for my dog to feel comfortable. I highly recommend Janiece.
Cynthia was so enthusiastic about caring for Willy and wasn’t worried about his medication requirements (including applying eye ointment) at all. Willy - who is a pro with Rover stays - seems to have taken on this new family with ease. We will definitely use Cynthia’s service in the future.
We needed a sitter on short notice. Dana responded quickly and we had our Sweetie Pie's sleepover booked. Got picture updates and the dog came home totally relaxed and happy. Definitely can recommend her. Super easy to communicate with and answered my questions right away. Thanks Dana.
Found my dog’s new sitter! I felt at ease on my trip because I felt I can trust Armando, he is attentive and kind! Booking with Armando was easy and he responded very quickly. His open availability is a huge plus and my dog looked happy when I picked him up so I know he had a fun filled weekend :D
I have a senior blind dog and she requires somone who is patient because she can be uneasy with new people. This was my 2nd time ever leaving my dog with a non family member and Alexandra was great. I asked for updates and she would respond quickly. I would definitely use Alexandra again for my Lola.
We boarded Kairo for 3 nights with Dane and Perla. Kai had not been out of the house on his own for over 2 years and we were nervous as we felt Kai’s anxiety of being alone. Dane and Perla generously allowed us to let Kai spend a couple hours on two days prior to our trip so Kai can get used to them and their house. Kai seemed to enjoy their nice backyard and the enclosed part of the house where the dogs usually stay. We were told of the company Kai would be having while we are gone and Kai seemed to have thoroughly enjoyed being with the other 2 dogs that were there who were the same size as him. Victor (Perla's dad) is who looks after them for the most part and walks them. We got to face time Victor and Perla when our times matched and Kai looked to be having a fun time every time we connected. Perla’s children too are lovers of days so we know Kai had a lot of affection that he needed while we were away. We were looking for a place as Kai’s regular vacation house and we think we found it. Thanks Perla, Dane, Victor and kids.
Popular requests near you
Select a filter and find qualifying Winnetka sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winnetka is €63
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winnetka average 10 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for dog boarding in Winnetka on Rover as of Jun 2026 was about €63 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, 8,107 sitters provided dog boarding in Winnetka. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 88% of Winnetka dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winnetka have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 10 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winnetka.
Rover makes it easy to find Winnetka dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 8,107 dog boarding sitters in Winnetka on Rover, so you’re sure to find the perfect match for your dog! In Winnetka, 94% of sitters offer daily exercise, 94% offer medication administration, and 89% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Connect anywhere with the Rover app
