Pet Boarding in Winthrop Harbor
Find a loving Winthrop Harbor pet sitter to watch your cat or dog overnight at your sitter’s home.

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Top rated Winthrop Harbor pet boarders

About: I got a puppy when I was 18 and she’s 13 now! I have another dog and 2 cats we love just as much as our human babies! I work from home so I am home all day to be able to love on your babies and give them any care they may need while you are away! I have a fully fenced in backyard with 2 playful dogs! Pets are allowed wherever humans are allowed in our house! This is their home, too.

“I’m so happy to have found Jacob to care for my two dogs on short notice. Jacob made everything easy and stress free. I will definitely call on him again next time!”


“Tessa and her husband took very good care of our dog Gus. We were very happy with the first visit and did an overnight stay which also went very well. Gus seemed very comfortable in their home. Tessa is very responsive and sent us pictures of Gus.”



“Our golden doodle Ricky was under the care of Jennifer and Aaron for about 10 days. Their dog also happened to be golden doodle, so Ricky had a great time playing with him. Jennifer took very good care of Ricky and gave me daily updates with photos and text messages. She was a very kind to put Ricky at ease at times when he barked at night due to new place anxiety by allowing him to sleep in her room. They had a big fenced backyard for dogs to play during pleasant Chicago summer weather. Ricky enjoyed the walks as well. Ricky came back happy and healthy. I will recommend Jennifer as a dog sitter in a heart beat and she will gladly be my go-to dog sitter when I am in Chicago next year. Thank you Jennifer.”


“There aren't enough stars available to give Yesina. She was awesome. Stoney loved her. She was just what he needed. She was very kind, good, stearn and loving with Stoney. Stoney loved her friendly and playful dogs and became one of the pack. She gave him the training he needed and he responded wonderfully. I trusted her right away. She gave me great training tips to continue with Stoney at home. When I first met her I knew it would be a great relationship! Thanks Yesina (and your hubby too) for everything!”

“Raquel watched my two big fluffy kids for an extended period and took excellent care of them. Her communication was great along with being flexible with change of plans. We will definitely be using her again for future trips!”



“Flynn loved his stay at Angela's! He had lots of attention and had fun playing with her dogs. We received plenty of pictures and updates and knew he was in good hands while we were away. She is very personable and clearly loves animals!”


“This was our first time using a pet sitter and in home boarding. Lorena is so sweet and caring to our pup Lucy. She kept in contact with us and that was so reassuring. Sent pictures and videos often. Lorena's home was set up in a way that was great for dogs...fenced in large yard, and no carpet for easy cleanup. Clean and tidy. Will definitely use Lorena again, happy to have found her!”


“Mike has taken really great care of our Puppy Bagheera!. Daily communication regards to puppy along with pictures made us feel like we were there with Bagheera. Definitely recommend Mike. Also looking forward to work with you for our future vacation.”


“Chucho had such a great stay with Diamond. He is a senior dog with many needs. He also needed multiple medications. Diamond was great following the care indications we provided and made sure he felt comfy and warm during this cold weather.”


About: I've had three dogs during ny life. I'm a dog person. Dogs are very special to me and you're pet will be treated as such. If any special needs are needed, please let me know. If you have any questions, please let me know. Available for boarding weekend or weekday. Must meet and great prior to boarding. If you need someone to care for your loved dog, I'd be happy to help. Fenced yard and fun loving dog. I have with children, 7 and 11 year old. We all love dogs. Daily walks. Also some trips to the dog park.

About: I absolutely love animals! I have taken care of various sorts of pets including hamsters, dogs, cats, fishes and birds. I have been involved in animal rescue and foster work. I love taking care of them ❤️ I own a Persian cat and four fishes, I look after them like they are my own kids. I have plenty of experience when it comes to taking care of cats, dogs, birds, and fishes. Your pet will feel at home when staying with me, I will make sure to love them like my own and play with them and look after them sincerely.

“Sandy is truly a doll! Used her multiple times now & she always sends adorable pictures, keeps me updated & even made some cute little bandanas for valentines day! I'd recommend her to anyone ❤”


“Ashley and her family took excellent care of my Little Lucy! She sent us pictures of Lucy sunbathing and taking walks with the family. Definitely will have them watch her again!”

Loving pet boarding sitters in your neighborhood
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Mary & Norman B.

“Mary took great care of my dog. She is very responsive. I would highly recommend her to take care of your furry baby too. I would definitely use her again.”


Mary D.
“Mary is the absolute best! She has been my go to for seven years and my two collie pups adore her! Mary goes above and beyond spending time playing with them, giving them their meds, sending picture updates, etc! My pups love their time with Mary and cannot wait until the next time they see her! The peace of mind that I have knowing that they are in her care is invaluable- she is responsible, a great communicator, and well organized. There is no one that I would trust more- I highly recommend!”


Norma G.Star Sitter

“My dog was well taken care of during my vacation, and I loved the photos and video she shared while I was gone. I will definitely contact her again when needed.”


Jacob Miles F.Star Sitter

“I’m so happy to have found Jacob to care for my two dogs on short notice. Jacob made everything easy and stress free. I will definitely call on him again next time!”


Tessa S.Star Sitter

“Tessa and her husband took very good care of our dog Gus. We were very happy with the first visit and did an overnight stay which also went very well. Gus seemed very comfortable in their home. Tessa is very responsive and sent us pictures of Gus.”




Jennifer & Aaron C.

“Our golden doodle Ricky was under the care of Jennifer and Aaron for about 10 days. Their dog also happened to be golden doodle, so Ricky had a great time playing with him. Jennifer took very good care of Ricky and gave me daily updates with photos and text messages. She was a very kind to put Ricky at ease at times when he barked at night due to new place anxiety by allowing him to sleep in her room. They had a big fenced backyard for dogs to play during pleasant Chicago summer weather. Ricky enjoyed the walks as well. Ricky came back happy and healthy. I will recommend Jennifer as a dog sitter in a heart beat and she will gladly be my go-to dog sitter when I am in Chicago next year. Thank you Jennifer.”


Yesenia C.
“There aren't enough stars available to give Yesina. She was awesome. Stoney loved her. She was just what he needed. She was very kind, good, stearn and loving with Stoney. Stoney loved her friendly and playful dogs and became one of the pack. She gave him the training he needed and he responded wonderfully. I trusted her right away. She gave me great training tips to continue with Stoney at home. When I first met her I knew it would be a great relationship! Thanks Yesina (and your hubby too) for everything!”


Raquel T.

“Raquel watched my two big fluffy kids for an extended period and took excellent care of them. Her communication was great along with being flexible with change of plans. We will definitely be using her again for future trips!”




Angela A.
Star Sitter


“Flynn loved his stay at Angela's! He had lots of attention and had fun playing with her dogs. We received plenty of pictures and updates and knew he was in good hands while we were away. She is very personable and clearly loves animals!”


Sarah M.

“Sarah was amazing! She took such great care of our dog and was even flexible when our travel plans changed! Definitely recommend Sarah for boarding.”


Lorena R.

“This was our first time using a pet sitter and in home boarding. Lorena is so sweet and caring to our pup Lucy. She kept in contact with us and that was so reassuring. Sent pictures and videos often. Lorena's home was set up in a way that was great for dogs...fenced in large yard, and no carpet for easy cleanup. Clean and tidy. Will definitely use Lorena again, happy to have found her!”


Charity D.


“Charity took great care of my dogs and was great at communicating with me.”


Michael H.

“Mike has taken really great care of our Puppy Bagheera!. Daily communication regards to puppy along with pictures made us feel like we were there with Bagheera. Definitely recommend Mike. Also looking forward to work with you for our future vacation.”


Diamond G.

“Chucho had such a great stay with Diamond. He is a senior dog with many needs. He also needed multiple medications. Diamond was great following the care indications we provided and made sure he felt comfy and warm during this cold weather.”


Jennifer S.

“Jenny was awesome!”


Rosa H.

“Rosa was super attentive with Ramses’ needs. She provided pics regularly and timely. Will defined book again with her!”


Brian P.
About: I've had three dogs during ny life. I'm a dog person. Dogs are very special to me and you're pet will be treated as such. If any special needs are needed, please let me know. If you have any questions, please let me know. Available for boarding weekend or weekday. Must meet and great prior to boarding. If you need someone to care for your loved dog, I'd be happy to help. Fenced yard and fun loving dog. I have with children, 7 and 11 year old. We all love dogs. Daily walks. Also some trips to the dog park.


Swagata H.
“Swagata is very good around pets, she absolutely loves animals! I have seen her taking care of cats, dogs, hamsters, birds and what not, and she has been very passionate always around them. She’s kind and gentle, and takes care of every pet like they are her own. So I will definitely vouch for her being a loving and caring pet sitter.”


Sandy D.Star Sitter

“Sandy is truly a doll! Used her multiple times now & she always sends adorable pictures, keeps me updated & even made some cute little bandanas for valentines day! I'd recommend her to anyone ❤”


Ashley R.Star Sitter

“Ashley and her family took excellent care of my Little Lucy! She sent us pictures of Lucy sunbathing and taking walks with the family. Definitely will have them watch her again!”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Boarding FAQs
Frequently asked questions about Rover
Typically, pet boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your pet in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winthrop Harbor.
Rover makes it easy to find Winthrop Harbor pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:
- Dogs and cats of all ages and abilities, including puppies and kittens
- Pet parents looking for a safe, loving alternative to a kennel or hotel
- Pets who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet 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 pet 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 pet boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
