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

Winterset, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I had never used a service like this before and I was so happy to find the right person to help care for August while I was away! Being new to the area I didn’t have anyone who could watch her while I left and I’m glad I found Azure! August was happy as can be!”

“Alexa was exactly what I needed to care for my Cat! As a first-time cat owner, I was really concerned of how my cat would respond to separated from me. Alexa immediately recognized her demeanor when I dropped her off and gave me the reassurance that I needed to know she was going to be okay. Alexa sent me photos through out the days we were apart and her bubbly personality made it easier knowing my cat was in the right hands. I couldn’t recommend her enough!”

“Jennifer and her family were amazing. She took wonderful care of our sometimes anxious pups. She even made sure they took their medicine and felt safe during a thunderstorm. Her home was clean and well-equipped for dog sitting. I would absolutely book with Jennifer again!”


“Couldn’t be happier with Bre’s first-time care for our pooch, Pepper! She was responsive with frequent reports and cute pics and conscientious with routines, flexible and easy to communicate with. A “match made in heaven” and we wouldn’t hesitate to rebook with Bre❣️”

“Ozzie had the best care at Stephanie’s. I was afraid he wouldn’t want to come home with me! She treated him just like her own and I feel very lucky to have had found her. I will definitely try to rebook next time we travel.”

About: What sets me apart from other pet sitters is my ability to provide structured, attentive, and compassionate care that meets both the physical and emotional needs of dogs. I am highly attentive to routines, behavior cues, and individual temperaments, allowing me to create a calm, safe, and consistent environment for each dog in my care. My dog-sitting skills extend beyond basic supervision to include proper exercise, reinforcement of positive behavior, and close observation to ensure overall well-being. I approach every responsibility with professionalism, reliability, and clear communication, giving pet owners confidence and peace of mind that their dogs are receiving exceptional, dependable care in their absence I have a flexible schedule and am available most of the time, allowing me to provide reliable and attentive care. While I am generally free during the week, I may occasionally have other commitments on weekends, though I communicate availability clearly in advance to ensure proper planning. I prioritize safety, trust, and a calm environment in every aspect of the care I provide. My upstairs apartment is clean, secure, and pet-friendly, with close supervision at all times to ensure pets remain safe and comfortable. I carefully follow each pet’s routine, dietary needs, and any special instructions provided, and I maintain a consistent and structured environment to reduce stress. My community offers designated areas for walking dogs, allowing for regular exercise in a controlled and safe setting. Through attentive care, clear communication, and respect for both the pet and the owner’s expectations, I strive to create a secure, trusting, and welcoming home where pets feel comfortable and well cared for
“Alex and Jayce were wonderful with our dog. So welcoming and very responsive. Our dog had a great time playing with their dogs. They sent great pictures and we could tell our dog was comfortable at their house. Would recommend to friends and family and will use them again!”

“I definitely recommend Kayla, she took care of my labrador puppy Arya for 4 nights. When I brought Arya she did not walk with her leash because she did not want to and when I went to look for her Kayla had taught her. Kayla take care of her with a lot of love, teach her new things, trained Arya and help her share with other dogs and cats. I am very satisfied and happy to be able to entrust the care of my baby Arya to such a committed person. Arya was really happy and have a great time, Kayla even give her new toys!!”

“Koopa is ver comfortable in their home. He walks in and walks directly to the back door to enjoy the fenced in backyard. Nan and her family administer his medication and take great care of him!”
“Emily did so awesome with our husky Loki while we were on vacation! We loved that he was able to have a fenced in yard and a bunch of other dogs to play with. Emily also sent us pictures and updates every day, which I appreciated a lot! Overall I would highly recommend Emily for boarding and will be booking with her next time I’m out of town.”

“This was George’s second stay with Sumer. He was excited when we dropped him off. And the next day he came home happy and tired! He had the chance to play with other dogs, which is great socializing for him. We appreciate the great care he receives with Sumer.”

“We were so lucky to have connected with such a great family at the last minute when our original sitter fell through. They helped him get warmed up with a meet and greet and then our 3 month old pup was excited to go back the next day to stay. He found his home away from for a week and was sad leaving his new friends. Diana and her family took great care of our boy while we were on vacation, helped house train him, and taught him a few commands. It was nice having peace of mind that he was in good hands and getting updates and pictures while we were missing our fur baby. 10/10 HIGHLY recommend!”

“We are so happy to have found Eddie. Leaving our girl behind while we were on vacation was difficult. Within the first day we felt so relieved Eddie sent a photo of Brooklyn sitting in a familiar way and we quickly believed she was totally comfortable. What a great feeling!! We found our go-to guy and as a result will be traveling more often sans Brooklyn. Thanks Eddie”

About: I've been around dogs ever since I was a child. I rarely come across a dog that I don't like or that doesn't like me! I currently do dog sitting and walking for friends and family and would love to expand my services to others looking for high quality dog care. I work part-time so I usually have a very flexible schedule with a lot of availability. Mornings through afternoons are usually the best times . I meet the needs of the dog owner when watching dogs in a client's home. I understand that dogs can have varying needs/schedules. I feel comfortable giving dogs necessary medicines and meeting any special needs. I can go the extra mile to make sure your dog(s) are happy and safe. I've even saved a dog that fell in a pool once!
About: To connect with your pet(s) on a super fun level and to really show them just how much we really do love and appreciate them! During the day 11 am to 2 pm At night 6 pm to 10 pm I would walk your pet around if needed but if the weather is appropriate. Being able to follow detailed instructions. I am consistent with the time I suppose to allow them to run and playing with them outside. I enjoy discovering new traits about pets.
“5 stars is not enough !! My dog had the best care here - we got pictures every day, they have a big fenced in back yard and are just the sweetest couple !! I don’t think one could find a better pet sitter.”

“We had a great experience with Amber. She was always quick to answer and flexible with our schedule to drop off/pick up. She kept us updated with pictures of Ginger and was very kind. Her dog Tater and Ginger had a great time together! We would definitely recommend her.”

“Carli was very professional and happily accepted my request to board Winston even while watching several other pups. Was very communicative and provided updated during Winston’s stay!”
The median cost per night for dog boarding in Winterset is $38
Dog parents share their Rover experiences - Winterset
She was great with my dog, super communicative, sent pics/vids, and was flexible when my plans changed. Being new to town, I was nervous leaving my dog with a stranger, but she made the whole thing smooth and my dog seemed to enjoy his time with her. Definitely would recommend!

Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog boarding

1. Search
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2. Meet In Person
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3. Book & Pay
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