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

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Top rated Westchester Gardens dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Duane and Lauren were wonderful to work with and took great care of our two dogs!!! Their communication was terrific and they were very flexible. We would love to have our dogs stay with them again!!”


“Julie was amazing. She has a lot of experience with rescued dogs and had the patience to let my dog get comfortable in the new environment. She has a fenced in yard so lots of playtime to let some energy out and she sent me many pictures to reassure me that my dog was doing well. I can’t talk her up enough! I’m excited to use Julie again for boarding Bear.”

“Kaycee was very helpful at our meet and greet, we hung out in their yard for a bit and she explained their setup and routine. She sent pictures while Ollie was boarded, which is much appreciated, and accommodated Ollie when he needed company overnight.”

“Bentley had a great time with you both! Thanks for taking such good care of our baby! We REALLY appreciated the pictures you sent while he was with you, too! We will absolutely book with you again.”

“We had a great experience with Erik. We felt very comfortable leaving our first time foster dog with Erik's family. They met with us before to see if it was a good fit. He was very gracious in dealing with our situation. We would recommend Erik and would book with him again.”
“Rona took excellent care of Basie and Mimi while we were away! She sent us regularly updates of the doggies sleeping, eating, and playing and she made sure that they wore their sweaters when they went outside in the chilly weather. Definitely would book again, she's amazing!”

“Anne kept me informed throughout Tut’s stay with updates on how he was doing and what they were up to. Tut had a great time on all the walks Anne took him on and enjoyed Tina as a playmate.”

“The kids were happy. Good communication, lots of photos and video. It was a great place with a good yard for them to play. She took good care of our perrhijos.”

“Val watched My dog Bentley over night and he seemed to enjoy himself. He was. He was nice and tired when I picked him up so I'm sure he had a good time with the other dogs as well. I will definitely use Val in the future to watch my pup.”

About: I love dogs and animals - they really are the best! I have owned three for many years, raising two from being puppies, and addressing challenging behavior with an older doggo, in addition to fostering multiple rescue dogs. I recently moved to WI, and my pets stayed home with my partner for now, and miss my furry companions and want to provide love and care for yours while I’m here! I am happy to work with you on what’s best, whether that is house sitting, boarding, or simply letting your animals out on walks or to go potty. Let’s chat! I currently work from home and have a remote job, so can provide your dog with any needs or attention that makes sense based on their schedule. I have some in-person meetings that occur throughout the week, and am generally around on the weekends regularly. If planning on boarding or daycare, my apartment is very dog-friendly, with many residents having pets and there are plenty of amenities available, whether walking around the neighborhood on leash or playing in the apartment’s fenced in dog run, that will give your pet what it needs. I can easily crate, take out for potty breaks, etc. I am also mindful of dog reactivity regardless of my own or neighbor’s dogs.
“Hope provided excellent communication and highly knowledgeable care for my senior dog. He felt so comfortable with Hope and they bonded during his five day stay with her. I was impressed and inspired by Hopes knowledge and attentiveness to detail. She keeps a regular daily routine that gave my dog so much reassurance and predictability, he quickly adapted. Hope was so dependable which gave me tremendous comfort while I was away. She quickly figured out his personality and his quirks and accepted him with humor, respect and love.”

“Emily was a great sitter! Toph was well taken care of and we received daily updates with photos. If anything came up she was in contact with us to let us know. From the pictures our dog was very happy and well loved while we were out of town.”

“Finny had a blast! I got updates every day and I could see how happy and content he was while I was on vacation. I was very comfortable knowing he was safe and having a great time, and when he got home he was good and tired. Thank you so much! I would be super happy to bring him back and would highly recommend.”

“Gilian was an amazing choice for boarding my dog! First we did a meet and greet at a local dog park, and then welcomed my dog to her home for a week+ of boarding. My anxious pup felt comfortable here after a couple days, and was well cared for. We can't do boarding kennels because of my dog's anxiety, so I'm so glad we found this service! I got updates daily about activities and behavior, as well as photos and videos! Gilian is knowledgeable handling anxious dogs, and she has good techniques on introducing dogs to new environments, dogs and people to help ease anxiety. I highly recommend Gilian!”

“Really appreciate Joan's kindness and care in watching Lacy. Lacy has stayed three times this summer, and we always feel so happy with the care she gets. Lacy comes home tired and happy!”
“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!”

“Amanda and her family were extremely accommodating and took care of my dog like he was their own. It was my first time using the app and I was nervous but she put that at ease with updates and pictures. Would definitely book again!”

“Rebekah and Alex were great to correspond with. Super flexible and accommodating regarding meet and greet, drop off and pick up times. Our dog had such a fun weekend at their house. We were provided pictures throughout the weekend and were ensured he was at the right place! Would definitely recommend and board with again!!”

“Yoki & Derek were fantastic hosts for Luke. I’ve been looking for reliable and trustworthy sitters for Luke since I travel quite often for work, and I think I found them. Luke will definitely be back as long as you’ll have him! ☺️”

Westchester Gardens dog parents share their Rover experiences
Joan was flexible and so understanding when we had to change plans last minute. She also took exceptional care of our dog including applying a salve to a wound and doing medication multiple times a day after we had to take our pup to the vet right before the visit started. 10/10 would recommend!

Nick and family were fantastic with our dog Iggy, who came home well exercised and relaxed. They have a great house and yard for accommodating the pooches, and their own friendly dog for company is a big plus. On top of it all, super quick and responsive communication throughout.

Kaycee and Robert are the best! They took such good care of our little dog, who has never spent time away from us. They took him on walks, played with him, and kept him warm and safe. Our dog loved Tank (their dog) and the kids. He had a blast with this lovely family. They are kind and warm people who took excellent care of our dog. It is evident that they are expert dog owners who have fostered and trained many dogs. We will definitely book them next time we leave town. We highly recommend them!

Jessica is a wonderful person and great the dogs. She was very accommodating after my flight delay and let me pick her up at midnight. She sent me many pictures of my dog including doggy yoga in her kitchen with all the dogs. hilarious. I will definitely book her again. Her large fenced back yard was great!

Cynthia always does a wonderful job with our Dog August! August can be a handful and loves to take lots of walks, which Cynthia is more than happy to do. I never have to worry about how she is going to be cared for and that’s the best part. I can go on my vacations with the peace of mind that Cynthia will do an excellent job.

Arabella stayed with Jennifer for 10 days. She was delightful. We received daily photos of Arabella and she managed to take her for walks, do zoomies with her, with her in the garden brush her teeth brush her hair give her daily belly rubs and make her feel loved. We never doubted for a minute that Jennifer truly cared for our dog. We will definitely use Jennifer again.

I can’t say enough wonderful things about Laura! We had a last minute care cancellation and needed a sitter for our 4 month old puppy. Not only did she take him in as one of her own, she helped safely build his confidence and helped him socialize with her gentle and well mannered dogs and cat of her own. I got multiple updates throughout the weekend, lots of pictures and best part is we were able to enjoy our best friend’s wedding because our worries were truly at ease knowing he was being taken care of by Laura. Will absolutely be looking to Laura first for any puppy care needs moving forward and I HIGHLY recommend having your fur baby stay with her ❤️

Zeppelin and his owners are beyond elated to have found Hannah and her doggies for boarding! From the meet and greet to pickup, we could not have asked for anything better. Hannah is intuitive, patient, kind, and has well trained doggies! She made sure to double check any special needs or requests and was very communicative during Zeppelin's stay. The pictures shared and behavior of our dog during drop off and pickup let us know he felt right at home. Hannah will be top of our list when looking for future care!

Bekah and Alex were amazing for Paka's 12-day mega-stay! Unfortunately on day #2, Paka did something clumsy in the backyard and had to be taken to the ER vet, but I so appreciated how communicative Bekah was through the entire process and how attentive she was with all of the aftercare. With multiple updates with photos per day, I didn't feel thousands of miles away. Paka still had a great time getting lots of cuddles and time basking on the deck. I would recommend them and book them again myself!

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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.
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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 Westchester Gardens.
Rover makes it easy to find Westchester Gardens 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.











