Dog Boarding in Winnetka
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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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 11%.
“Shahrzad was absolutely amazing with my dog! I left my pup with her for boarding, and I couldn't be happier. Her backyard is fantastic—huge, secure, and perfect for dogs to run around and play safely. Shahrzad kept me updated and took wonderful care of everything. It's such a relief to find someone you can genuinely trust. Highly recommended, and I will definitely be booking with her again!"”
About: USE THIS CODE FOR $20 OFF YOUR FIRST BOOKING https://www.rover.com/sit/sofiaf58007 Over the years, I’ve cared for many different animals from dogs and cats to guinea pigs and fish. I share my home with my senior dog, Cushla, a very sensitive dog I’ve cared for since she was a puppy. Caring for her has given me experience managing allergies, stomach issues, prescription food, medications, and the extra attention sensitive dogs need. I offer a calm, one-dog-at-a-time environment where your pet will receive my full attention and care. Since neighborhood cats occasionally visit the yard, I only accept well-socialized dogs up to 20 lbs who are comfortable around other animals and suited for a calm, low-stress home environment. I work from home full-time, so your dog will have constant supervision, personalized attention, and senior-friendly features like pet stairs, plus plenty of care and companionship. Your dog will stay in a spacious, calm home with plenty of room to relax and feel comfortable. I have a large, fully fenced backyard where they can safely explore, play on the lawn, and enjoy fresh air. I also have plenty of toys and balls to keep them engaged and happy. Inside, all furniture is covered with soft blankets so they can rest comfortably wherever they choose, and I have pet stairs available for dogs who need extra support getting up. Dogs are never kept in crates, and I always use a gentle, respectful approach to care, focused on making them feel safe, relaxed, and at home.
“As always, Melissa and Alexis are my go to for the care of Desmond? They are fantastic! I trust them completely. They are Desmond's home away from home. Thank you so much.❤️”
“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 dog was happy, so we were happy to see our pet satisfied! Thank you so much, Sonia. Hope to see soon! Definitely I will advise to choose Sonia as a sitter for your pet!”
“Annabelle and Ben are incredibly kind and professional. I had them watch my dog, Dante, for five days while I went out of town. I highly recommend them to anyone who is looking for a safe, fun, and loving environment for their dog. They welcomed Dante, who is not used to being away from the family, into their home and treated him as if he was their own. They even allowed Dante to sleep in their bedroom and relax on their living room couch. Annabelle and Ben have a large fenced-in yard where Dante was free to hang out and play with their very sweet pup Ranger. Dante also enjoyed fetching softballs from their kids and taking walks around their neighborhood. Annabelle and Ben were incredibly professional throughout the whole process. Annabelle invited me over for a meet and greet before booking and sent pictures daily while I was away. I could tell from the photos that Dante was very well taken care of. Dante came home calm and happy which is a true testament to the expert care that Annabelle and Ben provided. I will definitely use them again. In fact, I will be bringing Dante back in a few weeks!”
“Maryam was absolutely wonderful with Fiona. She was very accommodating when I needed to change the dates, which I truly appreciated. She also took the time to do a meet and greet beforehand so our dogs could meet, which made me feel even more comfortable. Her dog is very friendly and gets along well with small dogs, and Fiona fit right in. Maryam kept me updated with pictures and clearly took such great care of Fiona. It gave me so much peace of mind knowing she was in good hands. I would highly recommend Maryam to anyone looking for a caring, reliable, and thoughtful dog sitter. I will definitely be booking with her again.”
“Great experience. Great place. My dog seemed happy and playful after leaving there. I am sure he had a good time. I received pictures throughout the day of him and what he was doing.”
“For over a week, Monica took care of our little dog at her house. Monica was an incredible dog sitter. She is very warm and very clearly a dog lover. She sent me many pictures throughout the week and gave me updates re: his eating, walks, etc. This was my first time using Rover and I will absolutely use it again-hopefully with Monica! I cannot overstate how wonderful Monica is. She is so loving and responsible. I am very grateful!”
“Kiyarash was helpful during a sudden time of need. He took care of Cooper for a full night’s worth of boarding and I appreciate the daily updates with pictures. It seemed like his frequency and rotation of dogs is never more than one at a time so there’s also no need to worry about whether your dog specifically will he compatible with other dogs. His space is open and well-kept and I appreciated the house tour at drop off.”
“Patricia was great!! She was very kind and professional. I could tell she enjoyed caring for my little Zoey and gave her the attention and love she needed to feel safe in a new environment. I got lots of pics, which I appreciated. I will definitively be a returning customer. Thanks, Patricia!!”
“Renata and her family were incredible hosts for our 5 year old pug Anu. They were welcoming, provided lots of updates, and truly treated him like a part of the family. Renata shared a lot of photos throughout the long weekend that they watched Anu and I've never seen him happy and settled in so quickly at a new person's house. We felt super lucky to have Anu in the care of someone so nurturing and will definitely be back in touch with Renata the next time we need a dog sitter.”
“Mariia was so pleasant to work with. This was our first experience using Rover and we couldn’t be more satisfied. She sent us updates daily and made us feel comfortable keeping our pets with them the entire time. Highly recommend!!!”
“Our experience with Susan was fantastic! She took care of our two dogs as if they were her own. Susan provided us with daily updates and pictures while we were away. I highly recommend Susan to anyone looking for a trustworthy and caring pet sitter. We definitely plan to arrange more dog sitting with her. When we brought our dogs back home, they were very calm with no stress at all. Thank you, Susan!”
“Stanislava and her boyfriend were absolutely amazing with Minnie. My dog only eats homemade food and they were so happy to accommodate the requirements of being frozen and unfrozen for when it came to meals. They sent plenty of videos of Minnie running around with their dogs, which was awesome! I would absolutely book again! Thank you guys for taking such good care of her 🫶🏽🤍”
“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.❤️”
“I recently had the pleasure of entrusting my furry friend with this amazing dog sitter, and I couldn't be happier with the experience! Their genuine love for animals, attentiveness, and playful nature made my dog feel right at home. I highly recommend this dog sitter for their exceptional care and dedication. Five stars!”
“Levi was SO HAPPY here!! He was in the best hands and they gave us the best updates and sent him home with a packet of report cards and goodies ?? we are so grateful to have found somewhere that we felt Levi absolutely loved ! (He may not have wanted to come home ?) we will absolutely be booking again!!”
“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! 😊”
“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.”
Over 685 pet parents in Winnetka have booked dog boarding
Winnetka dog parents share their Rover experiences
I don’t normally leave reviews but Louella really stood out from other sitters I’ve used. She cared for my dog so well and made sure he was comfortable and happy the whole time. She kept me updated with messages, photos and videos, and always checked in to let me know how he was doing. She’s responsible, kind and very trustworthy, and it was clear she truly treated my dog like her own. I’m very grateful I found her and would highly recommend her to anyone looking for a sitter who truly goes above and beyond.
Thank you Shahrzad for taking such great care of Ollie! He usually needs to warm up with people but he loved you immediately and was so happy in all his videos! You were so accommodating and your home was perfectly comfortable and spacious for Ollie to run around and play. Thank you! We look forward to seeing you soon!
I was very nervous to leave our puppy, Reno, in anyone else's care besides family. But I was referred to Dana from a neighbor, and I'm glad we did. We finally found someone near our home to care for Reno! I was surprised to see that Reno was not nervous but seemed excited to enter her home. This gave me such peace of mind during my trip. Dana sent updates and photos at least once a day. I saw that Reno was making friends and having a good time. I was surprised to hear that he rarely barked or had any issues. I will be referring others to Dana, and will be using her services whenever I need. Thank you for taking care of our Reno!
Armando did an amazing job taking care of our 3 dogs. He was very responsive from the beginning and kept us updated throughout the entire stay with messages and photos, which gave us peace of mind. You can tell he genuinely cares about the dogs and makes them feel comfortable. When we picked them up, they were happy, relaxed, and clearly well taken care of. We would definitely trust him again and highly recommend him to anyone looking for a reliable sitter.
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.
Maryam was absolutely wonderful with Fiona. She was very accommodating when I needed to change the dates, which I truly appreciated. She also took the time to do a meet and greet beforehand so our dogs could meet, which made me feel even more comfortable. Her dog is very friendly and gets along well with small dogs, and Fiona fit right in. Maryam kept me updated with pictures and clearly took such great care of Fiona. It gave me so much peace of mind knowing she was in good hands. I would highly recommend Maryam to anyone looking for a caring, reliable, and thoughtful dog sitter. I will definitely be booking with her again.
She did great with my 2 first timer dogs. She was able to calmed them and earned their trust. She provided us their daily progress how they’ve coped up with their separation’s anxiety backed with pictures and videos. Frankie and Benjie will definitely be back under her care. Thank you Tanya!
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1. Search
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The median cost per night for dog boarding in Winnetka is $63
Why Choose Rover?
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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, the median cost of dog boarding in Winnetka is $63 per night, including service fees. Boarding your dog for one week typically costs $441. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winnetka dog boarding rates can be found as low as $26 to as high as $72 per night.
As of Jun 2026, 7,379 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 15 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 7,379 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, 93% offer medication administration, and 88% 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.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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