Dog Boarding in Winona
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Winona dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Our dogs have stayed with Lynne on several occasions. She is attentive to their special needs and keeps us updated on how they are doing so we can relax and enjoy our time away. Our pups seem to feel very comfortable in her care. :-)”


“Erica and Ciara were great!! Communicated very well. Even when we were busy and not always by the phone, pictures were great to look at when we did. Even when something came up, they let us know right away and we came up with a plan. Thank you for taking care of the boys!!”


“Cali did such a great job taking care of Lum for me! This was my first time ever using Rover and I was a little anxious about it. But Cali made me feel so relieved knowing my boy was safe and being taken care of. She sent me pictures and updates while I was gone which helped ease my mind and followed all of my instructions. I will definitely be booking with her again in the future and highly recommend her for pet parents that want the best experience for their fur babies!”


“Erica did a wonderful job taking care of Lily. I received updates, questions, pictures, videos, and texts about cute & funny things she did. I could tell Erica was caring towards Lily and enjoyed being with her. I will definitely call on her again”


“Ty was wonderful with our sweet Brant! Kept us well informed and updated throughout our time away from him. Our dog has no other pups at home, so any time he goes to a sitter, it’s truly a pup-cation and he came home zonked from all the play!”


“Thank you Rob and Sarah for taking such AMAZING care of Butter! He loved his stay, and is a tired and happy boy for our drive back :) Definitely recommend them!”


“Destiny was so great! Fenway is still sleeping after all the play that he got. They went above and beyond with baths, pictures, and play time! Will for sure be contacting again for future care!”


About: I’ve always had animals when I was at home with parents, once I moved out I got two of my own. I always enjoy seeing their growth and achievements and my dogs would love to have a friend come play for a little bit. I am currently working full-time at an autism center. I enjoy going home after work to play with my two dogs and making sure we go out on adventures and do different types of play and fun every day. I prioritize pet care in knowing that all dogs need love and I always make time for what they need. I have two friendly dogs of my own that are also great in their crates, but also can be left out during the day. Always make sure my animals have water and that they are fed. Prioritizing, they are happy and showing signs they are happy!

“My mini schnauzer stayed for a week. She was well taken care of and recieved lots of personal attention from the family. Kelsey provided detailed daily updates and several pics. We will be booking with Kelsey again and I highly recommend.”

“Our 3 boys enjoyed staying with Jenny and her pups. She took great care of them and loved the pictures and updates she sent. She is super easy to work with and boy oh boy, we're our guys tired when they got home. They had such a great time playing with Jenny and her pups. Highly recommend! We already have future dates booked with her!”


“Cassandra is awesome! She’s kind, responds quickly, sends pics, and genuinely seems to enjoy my dog! My dog feels right at home at her place with her dogs. We will use her as often as we can!”


“We felt very comfortable leaving both our dogs with Julie. She is a great communicator, considerate, and understanding of some family circumstances that unexpectedly came up. We will definitely use Julie again when we return to La Crosse. It's always a great feeling knowing our fur kids are safe, sound, and well cared for. Thanks so much, Julei!”


About: I was a veterinary technician for over 7 years, but I’m currently switching roles to healthcare. With that said, I would love to be able to still utilize my skills and knowledge to care for people’s furry friends on the side! I am trustworthy, loving, and caring, and I would hope that if I needed somebody to walk or care for my three dogs, they would have those same qualities. ***I do work M-F so if drop offs are needed during the work week it will have to be after 4:30 or 5:30 depending on the week*** I will be working M-F, but my hours would allow me to do later afternoon dog walks/drop-ins, and I would also be available on weekends to do dog walking or in-home pet care at my house. I have two dogs of my own who love a good long walk and love being around other dogs as well. *I can do weeknight stays if needed as long as you are okay with me being at work during the day. Hours are 8:30-5 and 7:30-4 with a day off every other week* I have a large backyard that is not fenced, but my two dogs go out there hooked up to their long tie-out. I have a camera in back to monitor them but can be on my deck watching them as well. They are very friendly and love to be around other dogs. I have the ability to crate dogs if I do in-home stays and have a spacious basement where my pups love to play with their other dog friends!

“I wish giving over 5 stars was an option! Rave reviews for Ashley! This was our first time using Rover and what a wonderful experience it was. Our 18 month old rescue LOVED his stay. Immediately he was very comfortable at Ashley’s home and with her wonderful dogs. I knew he was in great hands and he absolutely got a whole lot of TLC. Ashley gave us daily updates and tired our pup out! I really believe he was so entertained he didn’t have time to miss us. Endless thanks to Ashley and we will definitely be in contact with her for future stays!!! She’s the best!”


“WOW, just WOW! Amy is a rockstar Rover Sitter! Our pooch, Scooter, loved life the moment he stepped into her pooch-loving household. I felt so happy and relieved to have found Amy. This was a trip from GA to LaCrosse, WI for Christmas. I grew up in LaCrosse and would use Amy again in a heartbeat. She went above and beyond - trimmed his nails and I think he had a bath too. Plus, a fun little Christmas care package for our furbaby! You will love Amy and her darling kids to entrust your furbaby to! 100% recommended!”


About: I have always been an avid animal-lover. From childhood into adulthood, I have owned and cared for a variety of pets, including dogs, cats, small mammals, reptiles, birds & fish. My family & I currently share our home with two dogs, a bearded dragon, a Russian tortoise, & a ball python. I have several years of professional work experience in animal care (zoo, kennel care, walking, basic grooming) and wildlife / parks & recreation—both of which are relevant. I enjoy the outdoors and keeping all of our furry (& scaly) friends happy. I will board dogs, small mammals, reptiles & birds in my home! Upon request, I can do drop-in visits for cats or exotic animals within a 15 mile radius. I am currently a stay-at-home mom & so my schedule allows me to be at home majority of the time. If I need to leave the house, it’s never for more than a couple of hours. I have a large four-story home, which provides amble space for pets to play or to be separated if need be. I utilize crates for dogs who need or prefer it. Our yard is unfenced, so I use slip leads and tie-out cables for potty time.

“Ty did a great job with my 2 dogs. He was super prompt responding to messages and gave just the right number of updates so I knew things were going well. Even more importantly, the dogs were happy and relaxed when I picked them up. That is always the best sign! I really appreciate his care for my dogs.”


About: Hello! My name is Tyler. I have been pet sitting for friends and family for several years and have experience with multiple dog and pet households. I am trustworthy, honest and dependable and take pride in being neat and orderly. I have taken care of all breeds from small to large. I have been around dogs my whole life and have experience taking care of them. I look forward to walking your dog and keeping them active. I look forward to talking with you and determining if I will fit you and your pets needs. I’m currently a stay at home mom so I am around all day and able to give your pet the time and energy they deserve! I am able to take your dog on walks to give them exercise however long or short. I can feed your fur baby and play with their favorite toy.

“Kirsten and Kaleb have our Holly amazing care while we were gone for almost two weeks. They sent pictures every day and were so flexible with what we needed, even offering to keep Holly am extra day when we weren't sure we would get back on time. Holly doesn't always get along with other dogs but she loved their dog, Beau!”

Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Lynne R.Star Sitter

“Our dogs have stayed with Lynne on several occasions. She is attentive to their special needs and keeps us updated on how they are doing so we can relax and enjoy our time away. Our pups seem to feel very comfortable in her care. :-)”


Erica & Ciara M.

“Erica and Ciara were great!! Communicated very well. Even when we were busy and not always by the phone, pictures were great to look at when we did. Even when something came up, they let us know right away and we came up with a plan. Thank you for taking care of the boys!!”


Cali R.Star Sitter

“Cali did such a great job taking care of Lum for me! This was my first time ever using Rover and I was a little anxious about it. But Cali made me feel so relieved knowing my boy was safe and being taken care of. She sent me pictures and updates while I was gone which helped ease my mind and followed all of my instructions. I will definitely be booking with her again in the future and highly recommend her for pet parents that want the best experience for their fur babies!”


Erica K.

“Erica did a wonderful job taking care of Lily. I received updates, questions, pictures, videos, and texts about cute & funny things she did. I could tell Erica was caring towards Lily and enjoyed being with her. I will definitely call on her again”


Ty E.Star Sitter

“Ty was wonderful with our sweet Brant! Kept us well informed and updated throughout our time away from him. Our dog has no other pups at home, so any time he goes to a sitter, it’s truly a pup-cation and he came home zonked from all the play!”


Sarah & Rob O.
Star Sitter


“Thank you Rob and Sarah for taking such AMAZING care of Butter! He loved his stay, and is a tired and happy boy for our drive back :) Definitely recommend them!”


William L.Star Sitter

“We were needing last minute dog sitting and Bill was gracious enough to watch our pup. He was accommodating and provided updates for us. Our pup had a great time!”


Destiny S.

“Destiny was so great! Fenway is still sleeping after all the play that he got. They went above and beyond with baths, pictures, and play time! Will for sure be contacting again for future care!”


Breanna L.
About: I’ve always had animals when I was at home with parents, once I moved out I got two of my own. I always enjoy seeing their growth and achievements and my dogs would love to have a friend come play for a little bit. I am currently working full-time at an autism center. I enjoy going home after work to play with my two dogs and making sure we go out on adventures and do different types of play and fun every day. I prioritize pet care in knowing that all dogs need love and I always make time for what they need. I have two friendly dogs of my own that are also great in their crates, but also can be left out during the day. Always make sure my animals have water and that they are fed. Prioritizing, they are happy and showing signs they are happy!


Kelsey W.Star Sitter
“My mini schnauzer stayed for a week. She was well taken care of and recieved lots of personal attention from the family. Kelsey provided detailed daily updates and several pics. We will be booking with Kelsey again and I highly recommend.”


Jenny H.

“Our 3 boys enjoyed staying with Jenny and her pups. She took great care of them and loved the pictures and updates she sent. She is super easy to work with and boy oh boy, we're our guys tired when they got home. They had such a great time playing with Jenny and her pups. Highly recommend! We already have future dates booked with her!”


Cassandra B.Star Sitter

“Cassandra is awesome! She’s kind, responds quickly, sends pics, and genuinely seems to enjoy my dog! My dog feels right at home at her place with her dogs. We will use her as often as we can!”


Julie H.Star Sitter

“We felt very comfortable leaving both our dogs with Julie. She is a great communicator, considerate, and understanding of some family circumstances that unexpectedly came up. We will definitely use Julie again when we return to La Crosse. It's always a great feeling knowing our fur kids are safe, sound, and well cared for. Thanks so much, Julei!”


Cassandra T.
“Cassandra is the best dog parent I know! She loves every animal as if they are her own and is dedicated to ensuring they live their best life. On top of that, she has 7 years of veterinary technician experience. You have my word that you can trust her with your pets :)”


Ashley M.Star Sitter

“I wish giving over 5 stars was an option! Rave reviews for Ashley! This was our first time using Rover and what a wonderful experience it was. Our 18 month old rescue LOVED his stay. Immediately he was very comfortable at Ashley’s home and with her wonderful dogs. I knew he was in great hands and he absolutely got a whole lot of TLC. Ashley gave us daily updates and tired our pup out! I really believe he was so entertained he didn’t have time to miss us. Endless thanks to Ashley and we will definitely be in contact with her for future stays!!! She’s the best!”


Amy W.Star Sitter

“WOW, just WOW! Amy is a rockstar Rover Sitter! Our pooch, Scooter, loved life the moment he stepped into her pooch-loving household. I felt so happy and relieved to have found Amy. This was a trip from GA to LaCrosse, WI for Christmas. I grew up in LaCrosse and would use Amy again in a heartbeat. She went above and beyond - trimmed his nails and I think he had a bath too. Plus, a fun little Christmas care package for our furbaby! You will love Amy and her darling kids to entrust your furbaby to! 100% recommended!”


Justine O.
About: I have always been an avid animal-lover. From childhood into adulthood, I have owned and cared for a variety of pets, including dogs, cats, small mammals, reptiles, birds & fish. My family & I currently share our home with two dogs, a bearded dragon, a Russian tortoise, & a ball python. I have several years of professional work experience in animal care (zoo, kennel care, walking, basic grooming) and wildlife / parks & recreation—both of which are relevant. I enjoy the outdoors and keeping all of our furry (& scaly) friends happy. I will board dogs, small mammals, reptiles & birds in my home! Upon request, I can do drop-in visits for cats or exotic animals within a 15 mile radius. I am currently a stay-at-home mom & so my schedule allows me to be at home majority of the time. If I need to leave the house, it’s never for more than a couple of hours. I have a large four-story home, which provides amble space for pets to play or to be separated if need be. I utilize crates for dogs who need or prefer it. Our yard is unfenced, so I use slip leads and tie-out cables for potty time.


Ty C.

“Ty did a great job with my 2 dogs. He was super prompt responding to messages and gave just the right number of updates so I knew things were going well. Even more importantly, the dogs were happy and relaxed when I picked them up. That is always the best sign! I really appreciate his care for my dogs.”


Tyler B.
“Tyler has pet sat our dog (Jet) and cat (Granola) for us several times. From 3 days at a time up to 2 weeks. She has been respectful of our home and has been nothing short of wonderful. Pets love her, people love her and I know you'll love her too!”


Kirsten & Kaleb M.

“Kirsten and Kaleb have our Holly amazing care while we were gone for almost two weeks. They sent pictures every day and were so flexible with what we needed, even offering to keep Holly am extra day when we weren't sure we would get back on time. Holly doesn't always get along with other dogs but she loved their dog, Beau!”
Over 226 pet parents in Winona have booked dog boarding
Winona dog parents share their Rover experiences
Lynn is a repetitive care specialist for my Riley girl! Love how she follows directions, especially when all others fells short she came to my help last minute! Can’t every time but this was down to an emergency almost had to cancel plans. Riley is safe and trusts Lynn and always a fun time when my dog comes home wet I am a happy Mom!!

Cali did an excellent job and was wonderful to work with! This was our first time using Rover, and she made us feel really comfortable through the whole process. While we were away, and she sent photos and updates on our puppy. She made sure he had everything he needed - daily walks and car rides. We would absolutely book with Cali again.

Popular requests near you
Select a filter and find qualifying Winona sitters!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!
The median cost per night for dog boarding in Winona is $38
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.
Sitters in Winona average 8 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Winona is $38 per night, including service fees. Boarding your dog for one week typically costs $266. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winona dog boarding rates can be found as low as $26 to as high as $44 per night.
As of Aug 2025, 31 sitters provided dog boarding in Winona. 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 Winona dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 8 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 Winona.
Rover makes it easy to find Winona 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 31 dog boarding sitters in Winona 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.
