Dog Boarding in Winston, IL
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Top rated Winston dog boarders
“JoAnna and her family are so welcoming and love dogs as much as we do. We enjoyed the daily picture updates of our Lance having a great time! Thanks so much for taking such great care of our fur baby! -Wendy & family”
“First time using rover and Riley. She was fantastic. Our dog loved her from the start. Kept me updated as to how our dog was doing and I felt very comfortable having our dog in her care. Great experience!!”
About: I've had dogs in my life since I was young. The newest member of our family, Reeses, makes me smile every day and we're learning from each other so much, she just warms my heart. When I was a senior in H.S. I worked with a professional trainer, training German Shepherds. It was during this time I learned that I've got a great commanding voice that dogs want to listen to. In college I was the president of the animal rights club, and worked with animal shelters in the area. Next year I plan on taking some official training classes and starting my own dog training / sitting business. Until then I'd love to make some new furry friends and their people too. I work from home, so I'm able to take frequent breaks and spend time with our four legged friends. I start the morning off with a walk, spend lunch working on some training or going for a ride, and I'm home and ready to play right at five as soon as I turn my computer off. I'm free to take potty breaks throughout the day as needed as well. Dogs love a good routine, and I'm here to help make that happen. I want them to feel as comfortable as possible while you're away so you can come home to a stress free pup, and for you to feel comfortable knowing your loved one is being looked after by someone that cares and is there with them.
“Taylor was great! She sent lots of pictures and took Millie on a few walks a day which Millie loves. She also gave updates on how she playing with the other dogs that were there which puts our minds at ease.”
“I can't say enough great things about Ruth! She took excellent care of our 2 dogs while we went on vacation for a week. She provided them with snuggles, walks, and social time and provided us with peace of mind so we could relax. She sent us a few pictures and even some videos! I highly recommend Ruth and we look forward to seeing her again in the future!”
“We have used Lottie twice now and feel so comfortable leaving our dog with her. She is very quick to respond, easy to communicate with and sends photos/updates while watching our dog.”
“Mya really is a wonderful dog sitter, as she treats your pet as she treats her own, with great love. I always know Buddy Bear will get the best care when he stays with Mya. Buddy Bear is advancing in years, and we don't leave him often, but, it is great to know Mya will take special care of him and he loves being there!!”
“She is a really good host. Right from the start itself their dog and our dog connected as they both are of same breed. She was really caring and gave us intermittent updates as well with photos and text of how our dog was doing. Her whole family got connected to our dog really well and provided a homely feeling for our dog. Will definitely recommend them and will like to rover with them again.”
“Jacqueline was amazing! From making me feel welcomed right from the first message to going above and beyond with communication, photos, updates and flexibity. 11/10 would recommend, if you care about your furry friend, with Jacqueline you can rest assured they are in safe hands :)”
“Nicole was great with communicating and sending both picture and video updates. Rusty seemed comfortable and happy the whole time and very well cared for! Would definitely book with her again.”
“Cassie was excellent with our Dakota! We knew he was in great hands the entire time we were away. He came home tired and snoring, even putting himself to bed, so we knew he played a lot! Cassie sent us adorable pics during Dakota’s stay. Her house and fenced in yard are perfect for the pups! And her pup Goose was an excellent playmate for Dakota!”
“Will definitely be rebooking with Melanie anytime we are in need of a sitter for Daisy. Melanie is quick to respond to questions and did an amazing job with my anxious pup. She put my mind at ease which allowed me to have a great time on my vacation.”
About: I grew up taking care of horses and a cat. Once I got a place of my own, I adopted two dogs and got a cat. I currently have a puppy who I am teaching basic commands. I have always been an animal lover and enjoy meeting new furry friends! My family and I love animals and look forward to meeting yours! I currently work full time from home with limited travel, but I do have a flexible schedule that allows me to plan around work to walk dogs or do potty breaks. I have a fenced in yard with two friendly dogs and a cat. I can easily crate your pet if needed. I enjoy walking and my son loves to play fetch with dogs!
“Such an Awesome sitter when you needed. Very inviting during our meet and greet. Her dogs are very respectful and well trained by Kylie. Our Lulah was able to connect very quickly with Romeo and Shadow. We were video prompt through out the day which is awesome as well. We highly recommend Kylie as a to go Dog Sitter (Boarding). Very clean and organized home for Dogs. Thank you Much Kylie!!!”
“Nora was very accommodating with pick up and drop off times and communicated throughout our long weekend away. Trustworthy and dependable and no doubt Lilly had so much fun with the kitties 😊 would definitely use her again! Thanks Nora!”
About: I’ve grown up with dogs and cats in the household. My priority is care and love for your furry friends! When I see dogs in public, I want to pet them all day :) Currently working part-time as well as attending college. I live in a dorm—no pets allowed. Classes are from ~12PM until ~4PM and work evening/nights. Nights I am not working my schedule is wide open. I like to gain a sense of trust at first between me and dogs(holding my hand out to sniff, pets if warranted, etc); Steer away from other dogs in public if mine gets aggressive; always conscious of surroundings; Dogs brighten my day every time I see one!
About: I have cared for many pets over the years. We decided its tine to open our home to all the pet lovers who need vacation help. I am currently available all day to care for your pets. I do not work outside the home. I have the tine for extra love. I have 5 cats and 2 dogs of my own. I have a large over 1/2 acre lot for outdoor activities. I do not have a fenc so pets will be leashed or allowed to roam based on owner insight.
“Diane was absolutely amazing! She obviously loves animals and understands both pets and pet parents! I feel confident that she took great care of my baby. I would 100% book with her again!”
Loving dog boarding sitters in your neighborhood
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JoAnna W.
“JoAnna and her family are so welcoming and love dogs as much as we do. We enjoyed the daily picture updates of our Lance having a great time! Thanks so much for taking such great care of our fur baby! -Wendy & family”
Riley S.Star Sitter
“First time using rover and Riley. She was fantastic. Our dog loved her from the start. Kept me updated as to how our dog was doing and I felt very comfortable having our dog in her care. Great experience!!”
Joshua W.
“Josh has been watching our 3 dogs for us when we travel for the last couple years and he has proven to be very dependable. The best thing about Josh is that he not only takes care of our dogs, he plays with them. Luckily, I am not the jealous type because there are times when they seem more excited to see him than me! Seriously though, it is such a relief to not have to worry about them when we go out of town. We know that he will be there and, since they love him, they will not be too sad while we are gone.”
taylor m.
“Taylor was great! She sent lots of pictures and took Millie on a few walks a day which Millie loves. She also gave updates on how she playing with the other dogs that were there which puts our minds at ease.”
Ruth G.
“I can't say enough great things about Ruth! She took excellent care of our 2 dogs while we went on vacation for a week. She provided them with snuggles, walks, and social time and provided us with peace of mind so we could relax. She sent us a few pictures and even some videos! I highly recommend Ruth and we look forward to seeing her again in the future!”
Mark S.
“Mark and his wonderful family took excellent care of my new 3 month old poodle puppy. What a privilege to leave my pup with such good people.”
Lottie C.
“We have used Lottie twice now and feel so comfortable leaving our dog with her. She is very quick to respond, easy to communicate with and sends photos/updates while watching our dog.”
Mya G.Star Sitter
“Mya really is a wonderful dog sitter, as she treats your pet as she treats her own, with great love. I always know Buddy Bear will get the best care when he stays with Mya. Buddy Bear is advancing in years, and we don't leave him often, but, it is great to know Mya will take special care of him and he loves being there!!”
Tamara D.Star Sitter
“She is a really good host. Right from the start itself their dog and our dog connected as they both are of same breed. She was really caring and gave us intermittent updates as well with photos and text of how our dog was doing. Her whole family got connected to our dog really well and provided a homely feeling for our dog. Will definitely recommend them and will like to rover with them again.”
Jacqueline M.
“Jacqueline was amazing! From making me feel welcomed right from the first message to going above and beyond with communication, photos, updates and flexibity. 11/10 would recommend, if you care about your furry friend, with Jacqueline you can rest assured they are in safe hands :)”
Nicole M.Star Sitter
“Nicole was great with communicating and sending both picture and video updates. Rusty seemed comfortable and happy the whole time and very well cared for! Would definitely book with her again.”
Cassie B.
“Cassie was excellent with our Dakota! We knew he was in great hands the entire time we were away. He came home tired and snoring, even putting himself to bed, so we knew he played a lot! Cassie sent us adorable pics during Dakota’s stay. Her house and fenced in yard are perfect for the pups! And her pup Goose was an excellent playmate for Dakota!”
Melanie D.
“Will definitely be rebooking with Melanie anytime we are in need of a sitter for Daisy. Melanie is quick to respond to questions and did an amazing job with my anxious pup. She put my mind at ease which allowed me to have a great time on my vacation.”
Calista C.
“I would trust Calista with any pets I’ve ever owned. I’ve gotten the pleasure of being around her with her own cat and dogs, and I have gotten to see how she handles others animals. She genuinely cares about their wellbeing and understand how important communication is being herself and pet owner!”
Kylie F.
“Such an Awesome sitter when you needed. Very inviting during our meet and greet. Her dogs are very respectful and well trained by Kylie. Our Lulah was able to connect very quickly with Romeo and Shadow. We were video prompt through out the day which is awesome as well. We highly recommend Kylie as a to go Dog Sitter (Boarding). Very clean and organized home for Dogs. Thank you Much Kylie!!!”
Maggie A.
“My dog had such a fun time staying with Maggie! She did a great job watching her, keeping us updated and ensuring she was well cared for!”
Nora S.Star Sitter
“Nora was very accommodating with pick up and drop off times and communicated throughout our long weekend away. Trustworthy and dependable and no doubt Lilly had so much fun with the kitties 😊 would definitely use her again! Thanks Nora!”
Tyler R.
About: I’ve grown up with dogs and cats in the household. My priority is care and love for your furry friends! When I see dogs in public, I want to pet them all day :) Currently working part-time as well as attending college. I live in a dorm—no pets allowed. Classes are from ~12PM until ~4PM and work evening/nights. Nights I am not working my schedule is wide open. I like to gain a sense of trust at first between me and dogs(holding my hand out to sniff, pets if warranted, etc); Steer away from other dogs in public if mine gets aggressive; always conscious of surroundings; Dogs brighten my day every time I see one!
Alyssa B.
About: I have cared for many pets over the years. We decided its tine to open our home to all the pet lovers who need vacation help. I am currently available all day to care for your pets. I do not work outside the home. I have the tine for extra love. I have 5 cats and 2 dogs of my own. I have a large over 1/2 acre lot for outdoor activities. I do not have a fenc so pets will be leashed or allowed to roam based on owner insight.
Diane M.
“Diane was absolutely amazing! She obviously loves animals and understands both pets and pet parents! I feel confident that she took great care of my baby. I would 100% book with her again!”
Popular requests near you
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1. Search
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The median cost per night for dog boarding in Winston is $33
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Sitters in Winston average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 37 sitters provided dog boarding in Winston. 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, 93% of Winston dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 12 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 Winston.
Rover makes it easy to find Winston 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 37 dog boarding sitters in Winston on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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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