Dog Boarding in Winnetka, IL
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winnetka dog boarders
“Thao was absolutely amazing! She took such wonderful care of our two dogs, Freyja and Odin. From the very beginning, Thao was incredibly responsive and quick to reply to all of our questions before we even booked. Throughout their stay, she kept us constantly updated with lots of fantastic pictures, which gave us great peace of mind knowing they were happy and in good hands. We are especially grateful for how super flexible and accommodating Thao was with a couple of our last-minute changes of plans. It really helped reduce our travel stress! We couldn't have asked for a better sitter. Thao will definitely be our go-to sitter for all our future trips. We highly recommend her!”
“Norman’s stay with Naomi and Johann went off without a hitch. He felt at home with them and got along well with Milo. We enjoyed receiving the regular updates and pictures they sent as well!”
“Ella took great care of our dog Sid! She’s very warm and clearly loves dogs. Communication was excellent, and we really appreciated the photo updates while we were away. Sid was in great hands. Highly recommend!”
“Nancyanne was a terrific sitter, her house is amazing and I had full confidence that she would take great care of my pup on our 7 day vacation. Would recommend her to anyone looking for quality boarding service for their dog.”
“We’ve been preparing for this long stay with a few overnight stays to get our dog Poppy To get acclimated. Poppy stayed with Noor and her family for 12 nights!! We got updates and pics regularly. Poppy seemed so happy and cared for with them when I came To pick her up she didn’t want to leave right away. Really appreciate all of Noor’s Communication.l Plus all the love her family members have to apply. We’re thrilled to have a found a caring sitter.”
“Another wonderful stay with Kaz and Akemi! Six days of playing, walks and being loved! Thank you for all the pictures and videos - I feel like I knew what he was doing the whole time.”
“Fantastic experience with Laura and Vladimir. Communication was great throughout. They sent pictures and updates on the dogs daily. Both my dogs seemed really happy when I picked them up. Would definitely recommend and use them again.”
“Kristina and her family took such great care of Feena! They made her feel right at home - and cared for Feena as if she is their own pet. It is such a relief to know that Feena was so comfortable with Kristina. I will definitely ask Kristina and her family to sit for Feena again in the near future.”
“Kim is responsive and friendly and sweet with my babies. She did some extra travel and pickup of meds I didn’t plan for without hesitation. Having her with my kitties gave me one less thing to worry about!”
“Gunter had another great stay with Merrick! He consistently provides updates on how he is doing and sends cute pictures. It’s so nice having a reliable place for Gunter to feel comfortable and have fun while I am out of town worry-free.”
“We had a great experience with Meghan! Freddy was happy, well cared for, and clearly received lots of attention while we were away. Communication was excellent throughout the stay, and we really appreciated the updates and photos. We felt completely at ease knowing he was in such good hands and would happily book again.”
“This was my first long trip away since getting Clifton and I was so lucky to find Jeff and Ron. They gave great updates and took great care of Clifton. I picked him up and he was happy and calm! Will not hesitate to send Clifton back for a stay.”
“Marija was amazing! She sent a lot of pictures and updates during Rookie’s entire stay. It was so nice knowing she was safe and getting a lot of love while we were gone!”
“Janette and Charlie were so thoughtful and caring in their communication regarding my dog. I appreciated their daily updates, pictures and even a video! We'll definitely use Janette and Charlie again!”
“Brian took great care of my dog and asked thoughtful questions to ensure my dog’s first stay with him would go well. He provided a picture daily and my dog was happy when I picked her up.”
“Cynthia is an outstanding sitter and a great person. She took the time to get to know me and my dog while showing me her house, which was very comforting! Cynthia also sent me timely updates and complied with all food requests, we will definitely be back! 5 stars!”
“Juilia was great. She was very responsive and did a lot of activities with Nico to ease him into a new environment. I would absolutely leave my dog with her again.”
“Clarissa did an amazing job of watching my dog, Peaches, for several nights. She was very responsive and provided photo updates each day. Her dog, Herkie, was also a great host and was very patient with Peaches entering his space. I would definitely recommend her to watch your dog!”
Winnetka dog parents share their Rover experiences
Rebeca was amazing with my dog Moose, who is a 75 pound American Bully! My dog stayed with Rebeca for 2 nights and 3 days and I cannot give her enough compliments. Not only did Rebeca have a huge yard for Moose to run around in, they were also extremely active for the entirety of the stay and Moose even got to play with some other dogs. Oh and the best part, Rebeca was sure to send me tons of pictures throughout his stay. Rebeca was a great dog sitter and I would easily recommend her to anyone looking.
I always worry when leaving my fur baby due to some bad prior experiences. Ella and Sydney were very kind, knowledgeable, accommodating, responsible, and caring. They communicated with me throughout the visit. Athena had such a great time that she didn’t want to leave. If you are on the fence on whether to book with Ella or not do not hesitate before some other lucky family reserves them. Thank you again!!!
We had the absolute best experience with Mia’s sitter. She was simply amazing, sending us regular pictures and updates, giving Mia a bath, making sure she was well fed, and treating her with so much care and attention. Mia clearly loved her home and her four-day mommy, and we felt completely at ease the entire time.
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.
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 €50
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 9 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, 5,239 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, 91% 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 9 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 5,239 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, 95% offer medication administration, and 90% 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.
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