Dog Boarding in Oakwood Village, Madison, WI
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Oakwood Village dog boarders

“Loving family who took take of our 4 months old puppy with such care. We told them Plato working on potty training and they were patient with him. The pupper had a blast hanging out with their kids and I loved seeing the daily updates. I would book them again the next time we need help!”


“This was the 2nd time Katie and Samuel’s family took care of Jarvis while we were away. We were very excited when they were available for these dates because Jarvis had a great time with them the first time. They did such an amazing job with him again and it really seemed like Jarvis felt right a home. They always send frequent updates and pictures which is really appreciated :)”


“Lindsey was great with my dog! She made sure to update us with photos and activities throughout the days. Thank you Lindsey for showering my fur baby with love and lots of walks!💕”


“Janiece was really kind and patient with my super old senior pup who is almost 16. Super thankful for someone who is caring and understanding of an old pups needs.”


“Christine is the absolute best. She made us feel very comfortable with leaving our pup and was awesome about keeping us updated. I think our dog liked being with Christine more than at home! It was such a blessing finding such an amazing dog sitter!!!”


“Polyanna is a very communicative and responsive, my dog Ziggy had a great time! She even gave a good recommendation for a no pull dog harness as well. I would recommend Polyanna for anyone looking for a dog sitter!”


“Mary took our dog for our wedding weekend and she was great! Pugsy had a great time with her dog, going on a walk, and going to the dog park! She sent pictures and we did not worry about Pugsy at all! We will definitely book with Mary in the future!”


“I had a fantastic experience with Michelle and her family caring for Cinnamon! They asked plenty of questions beforehand and made sure I knew there would be other dogs boarding at the same time, which I really appreciated. They sent me lots of update photos and videos, keeping me in the loop, and were so pleasant to work with. I would choose them again to look after my pup!”


“Cleda was very flexible when my dog’s care needs changed due to an injury that occurred a few days before she was to be boarded. Cleda was very accommodating and I was able to relax while away knowing my dog was in good hands. She got lots of one on one attention from Cleda which is exactly what she needed. Cleda also made arrangements to limit my dog’s physical activity, which was ordered by the vet after the injury. I will definitely be booking again!”


“Michelle (and family) took excellent care of our dog while we were out of town for 2 days, even keeping her calm during a storm. Great communication, too!”


“Sure! Here's a thoughtful review you can leave for Ryan and Martha: --- Ryan and Martha were absolutely wonderful with Yogi! From the start, their communication was excellent — clear, prompt, and always thoughtful. They made dropoff and pickup incredibly easy and were very flexible with the timing, which we really appreciated. Throughout Yogi’s stay, they sent us regular updates and the sweetest photos that clearly showed how happy and comfortable he was. It gave us so much peace of mind knowing he was in such good hands. You can tell they genuinely care about animals and treat them like part of the family. We would absolutely trust them with Yogi again and highly recommend them to anyone looking for kind, responsible, and communicative pet sitters.”


“Julie was absolutely fantastic. She knows dog behavior very well and I completely trusted her with my 12 week old puppy who is very nervous. Julie went above and beyond to make sure my puppy was comfortable and well taken care of. Highly recommend!”


“Robert did an excellent job hosting our dog for a week at his house. We received regular updates with photos and he was incredibly responsive, always replying in a timely fashion. When we first met, he struck me as a true "dog person" which is what we wanted! I would recommend Robert to anyone looking for a dog sitter.”


“One of the best providers on Rover! Amy is reliable, professional, and we can tell she truly enjoys caring for pets. If our pup could talk we are positive he would be asking us when he can go for another visit!”


“Edith was great with our puppy Artemis! We were able to meet beforehand for a short notice meet and greet before the holidays. Artemis got along really well with her two dogs and it seemed like he was having a lot of fun throughout the day- he came back exhausted and happy to see us after a couple of weeks, but we could tell that he was well taken care of. Edith sent frequent picture updates, and we felt like he was in good hands the whole time. I would definitely book Artemis here again in the future!”


“Emily and her family were so great with Jarvis! They sent plenty of update pictures and he seemed to have an amazing time!! We will definitely be looking to have them take care of Jarvis again :)”


“I am very satisfied with the care that Grace provided to my dog Goldie. She took good care of her and sent pictures along with updates during her stay. I would recommend Grace and would certainly request her again the next time Goldie needs to be boarded.”


“Neko came home exhausted so he must have had a wonderful time! Judd and Becky were so kind and worked well with us on a last minute request and we will absolutely use them again!”


“We always feel so comfortable whenever Ryan, Jocelyn and there two girls watch Turbo! We know how well he is being taken care of and he loves it too!”

Loving dog boarding sitters in your neighborhood
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Natalie B.Star Sitter

“Natalie was amazing! She took such good care of our girls while we had a few days away. Would absolutely book again!”


Kristin & Bruce M.Star Sitter

“Loving family who took take of our 4 months old puppy with such care. We told them Plato working on potty training and they were patient with him. The pupper had a blast hanging out with their kids and I loved seeing the daily updates. I would book them again the next time we need help!”


Katie & Samuel W.Star Sitter

“This was the 2nd time Katie and Samuel’s family took care of Jarvis while we were away. We were very excited when they were available for these dates because Jarvis had a great time with them the first time. They did such an amazing job with him again and it really seemed like Jarvis felt right a home. They always send frequent updates and pictures which is really appreciated :)”


Lindsey C.
Star Sitter


“Lindsey was great with my dog! She made sure to update us with photos and activities throughout the days. Thank you Lindsey for showering my fur baby with love and lots of walks!💕”


Janice B.Star Sitter

“Janiece was really kind and patient with my super old senior pup who is almost 16. Super thankful for someone who is caring and understanding of an old pups needs.”


Christine N.Star Sitter

“Christine is the absolute best. She made us feel very comfortable with leaving our pup and was awesome about keeping us updated. I think our dog liked being with Christine more than at home! It was such a blessing finding such an amazing dog sitter!!!”


Polyanna N.Star Sitter

“Polyanna is a very communicative and responsive, my dog Ziggy had a great time! She even gave a good recommendation for a no pull dog harness as well. I would recommend Polyanna for anyone looking for a dog sitter!”


Mary Z.Star Sitter

“Mary took our dog for our wedding weekend and she was great! Pugsy had a great time with her dog, going on a walk, and going to the dog park! She sent pictures and we did not worry about Pugsy at all! We will definitely book with Mary in the future!”


Michelle F.

“I had a fantastic experience with Michelle and her family caring for Cinnamon! They asked plenty of questions beforehand and made sure I knew there would be other dogs boarding at the same time, which I really appreciated. They sent me lots of update photos and videos, keeping me in the loop, and were so pleasant to work with. I would choose them again to look after my pup!”


Cleda W.
Star Sitter


“Cleda was very flexible when my dog’s care needs changed due to an injury that occurred a few days before she was to be boarded. Cleda was very accommodating and I was able to relax while away knowing my dog was in good hands. She got lots of one on one attention from Cleda which is exactly what she needed. Cleda also made arrangements to limit my dog’s physical activity, which was ordered by the vet after the injury. I will definitely be booking again!”


Michelle S.

“Michelle (and family) took excellent care of our dog while we were out of town for 2 days, even keeping her calm during a storm. Great communication, too!”


Ryan & Martha M.

“Sure! Here's a thoughtful review you can leave for Ryan and Martha: --- Ryan and Martha were absolutely wonderful with Yogi! From the start, their communication was excellent — clear, prompt, and always thoughtful. They made dropoff and pickup incredibly easy and were very flexible with the timing, which we really appreciated. Throughout Yogi’s stay, they sent us regular updates and the sweetest photos that clearly showed how happy and comfortable he was. It gave us so much peace of mind knowing he was in such good hands. You can tell they genuinely care about animals and treat them like part of the family. We would absolutely trust them with Yogi again and highly recommend them to anyone looking for kind, responsible, and communicative pet sitters.”


Julie Z.Star Sitter

“Julie was absolutely fantastic. She knows dog behavior very well and I completely trusted her with my 12 week old puppy who is very nervous. Julie went above and beyond to make sure my puppy was comfortable and well taken care of. Highly recommend!”


Robert N.Star Sitter

“Robert did an excellent job hosting our dog for a week at his house. We received regular updates with photos and he was incredibly responsive, always replying in a timely fashion. When we first met, he struck me as a true "dog person" which is what we wanted! I would recommend Robert to anyone looking for a dog sitter.”


Amy G.

“One of the best providers on Rover! Amy is reliable, professional, and we can tell she truly enjoys caring for pets. If our pup could talk we are positive he would be asking us when he can go for another visit!”


Edith S.Star Sitter

“Edith was great with our puppy Artemis! We were able to meet beforehand for a short notice meet and greet before the holidays. Artemis got along really well with her two dogs and it seemed like he was having a lot of fun throughout the day- he came back exhausted and happy to see us after a couple of weeks, but we could tell that he was well taken care of. Edith sent frequent picture updates, and we felt like he was in good hands the whole time. I would definitely book Artemis here again in the future!”


Emily B.Star Sitter

“Emily and her family were so great with Jarvis! They sent plenty of update pictures and he seemed to have an amazing time!! We will definitely be looking to have them take care of Jarvis again :)”


Grace R.

“I am very satisfied with the care that Grace provided to my dog Goldie. She took good care of her and sent pictures along with updates during her stay. I would recommend Grace and would certainly request her again the next time Goldie needs to be boarded.”


Becky & Judd W.Star Sitter

“Neko came home exhausted so he must have had a wonderful time! Judd and Becky were so kind and worked well with us on a last minute request and we will absolutely use them again!”


Ryan & Jocelyn R.Star Sitter

“We always feel so comfortable whenever Ryan, Jocelyn and there two girls watch Turbo! We know how well he is being taken care of and he loves it too!”
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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 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.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog 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 Oakwood Village.
Rover makes it easy to find Oakwood Village 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
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.
