Dog Boarding in Winchester, IN
Find a loving dog sitter to watch your dog overnight at your sitter's home.
More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Top rated Winchester dog boarders
“My dog had so much fun at her house. We got constant updates and photos to show us how she was doing. I would most definitely use her in the future.”
“Penny was so good with our baby, she took great care of her and stayed in touch with us the whole time. We would recommend her to take care of anyone’s pets, and we will definitely be using her again. Thanks Penny!”
“Very comfortable stay at Steve's. Casey had a wound at the time, but he cared for it greatly. He administered meds and kept me at a complete peace of mind.”
“Hilary was great. She sent pictures everyday, and I could tell my dog was having a great time in them. She made sure he got all the things he likes: walks, play, and cuddles. Very easy to work with too with good communication between me and Hilary. My dog was in good spirits when I picked him up like he was at home there.”
“Sarah was a great fit for Duke. I had to leave town for a funeral so short notice and she was very accommodating. She kept me updated with how Duke was doing through my trip. I would recommend her for everyone to use.”
“Brandi was awesome. Sophie was instantly at home the minute we arrived. Brandi sent daily pictures and messages. We felt super comfortable leaving Sophie in her care.”
“Laurie was absolutely great! She was so good to Odin and welcomed into her home as if he was her own. He adapted well to her family and she kept me updated with messages and pictures throughout his stay. We are so thankful for her!”
“Haylie was so wonderful to work with! She sent me updates and pictures throughout my trip and allowed me to extend Seeley's stay with her family on short notice when we had some unexpected issues. This was his second time staying with Haylie, and I am sure it won't be his last!”
“Aubrey took care of Xena. We received photos and video fault. Will use her again.”
“John took excellent care of Ginger for a few days over the Thanksgiving holiday. She does have a bit of separation anxiety but he made sure she got plenty of attention. Sent us pictures and reports throughout her visit.”
“Virginia met us at a local park so we could introduce our shepherd to her before her stay. We talked for almost an hour.... it was wonderful and Virginia is amazing with people as well as dogs. She sent us pictures of our Maggie while we were away to keep us updated on how she was doing. I definitely would use Virginia again in the future and recommend her to anyone needing a loving caretaker for their pet when they are away.”
“We loved Casey and her little family. Copper was well taken care of and had fun with the dogs that were there. Glad he could have vacation while we did!”
About: With four years of professional kennel experience, I understand that every dog has unique needs and personalities. I go beyond basic pet care, providing attentive, personalized care that gives your dog the comfort and routine they’re used to as if it were you. From playtime and exercise to medication management, I bring a trained eye to every detail, ensuring your pup is safe, happy, and stress-free. I’m always excited to make a new furry friend and treat them like family! I am currently a student at Ball State University with a part time job at Menards. I only have classes a couple hours a day around noon. I am looking to fill up my mornings and evenings with a care that I deeply enjoy and am passionate about! For house sitting, I stay overnight and follow the pet’s normal routine, including feeding, walks, playtime, and medication if needed. I provide companionship, keep the home clean, and send regular updates with photos to keep the owner informed and reassured. For drop-in visits, I stop by three times a day for about 20 minutes each visit. During each drop in I handle feeding, potty breaks, playtime, and basic care, while making sure to send detailed updates and pictures after every visit.
“My dog looked well cared for when I picked her up. Xander sent me photos of my dog enjoying herself while I was gone. I would definitely consider him again if I needed a dog sitter.”
About: i have lots of experience walking dogs and pet sitting! with my rover experience and dog walking for the animal shelter i can assure you that your pet would be in good hands! i work third shift four days a week so i have a very open schedule for walks and drop ins. my best times are 9am-noon and 4pm-7pm but i am open to requests at any time:) while walking dogs i ALWAYS keep them on leash. i’m comfortable helping with whatever you need whether that’s just hanging out or maybe brushing your pet:) just ask!
“Nicole is amazing! She takes Nova on walks and to the dog park. She takes very good care of my baby Nova. She even offers to do pick up and drop off for your pet. I would recommend her to anyone :)”
About: I’ve taken care of my families dogs since I was a little girl. I would feed them, take them outside, and go for walks with them. Im currently working part time, so I have plenty of time to play & care for your fur babies! My schedule is pretty flexible to fit everyone’s needs. I live in a house with my children. I don’t have a fenced in yard, so I can crate or put your dog on a leash so they can have outside time.
About: I’ve been a dog owner and foster parent my whole life. I’ve trained and owned all kinds of dogs from Jack Russels and Pomeranians to Great Danes and Golden Doodles. The relationships I build with dogs are enriching and rewarding. The innocence and desire to just be themselves is what I love about animals. I treat my new dog friends like family and I believe they prosper in a relationship that promotes their inner dog as well as setting boundaries that help the human/canine relationship prosper. I embrace the belief of calm assertive dominance and find it that dogs seem to find peace in me being in that role. I am a stay at home parent whose availability is an asset that I utilize for the sake of the animals I care for. I hope to one day befriend your best friend. I’m a stay at home father of 10 and 12 yr old boys. I raise 2 dogs, 2 cats, and 24 chickens. I have lots of flexibility to ensure the care needed for you pet. I love to spend time with animals in the environment they feel most comfortable. With my flexible schedule and the abundance of land on my property and in my locale, I know I can fit the needs of your furry friend.
About: We love dogs! We have a female English massiff that stays inside, and currently care for 4 hunting hounds in our outside kennel. I can care for your dog any way that you see fit. If you are more comfortable with your dog staying in their own home I can do that. I am also available for drop ins. And walks. I do work a part time job Wednesday- Saturday 9:30-5pm. I have 3 children so your pet must be friendly with children. We are a dog loving family. We look forward to hearing from you and getting to know you and your wonderful dog. Feel free to ask me any questions. I currently work a part time job from 9:30am-5pm Wednesday- Saturday. On my days off and before and after work I will have time to spend with your dogs. I currently am not offering sitting at my house. But I’m more than happy to care for your animals at your home, providing any services that you need.
About: I've taken care of dogs since I was kid. To me they are like family and should be treated with love. I have 3 of my own that I've had since they were puppies. I'm currently working part time so I'm using my extra time to help others with their fur babies. I'm home most of the time so I can give them extra attention. My back yard is fenced in. I have dog crates available if they need it. Tons of toys and treats too. Clean and bug free home.
Loving dog boarding sitters in your neighborhood
Search Results
Adrianne J.
Star Sitter
“My dog had so much fun at her house. We got constant updates and photos to show us how she was doing. I would most definitely use her in the future.”
Penny H.Star Sitter
“Penny was so good with our baby, she took great care of her and stayed in touch with us the whole time. We would recommend her to take care of anyone’s pets, and we will definitely be using her again. Thanks Penny!”
Steve L.Star Sitter
“Very comfortable stay at Steve's. Casey had a wound at the time, but he cared for it greatly. He administered meds and kept me at a complete peace of mind.”
Hilary H.
“Hilary was great. She sent pictures everyday, and I could tell my dog was having a great time in them. She made sure he got all the things he likes: walks, play, and cuddles. Very easy to work with too with good communication between me and Hilary. My dog was in good spirits when I picked him up like he was at home there.”
sarah s.
“Sarah was a great fit for Duke. I had to leave town for a funeral so short notice and she was very accommodating. She kept me updated with how Duke was doing through my trip. I would recommend her for everyone to use.”
Brandi C.
“Brandi was awesome. Sophie was instantly at home the minute we arrived. Brandi sent daily pictures and messages. We felt super comfortable leaving Sophie in her care.”
Laurie S.
“Laurie was absolutely great! She was so good to Odin and welcomed into her home as if he was her own. He adapted well to her family and she kept me updated with messages and pictures throughout his stay. We are so thankful for her!”
Haylie H.Star Sitter
“Haylie was so wonderful to work with! She sent me updates and pictures throughout my trip and allowed me to extend Seeley's stay with her family on short notice when we had some unexpected issues. This was his second time staying with Haylie, and I am sure it won't be his last!”
Aubrey J.
“Aubrey took care of Xena. We received photos and video fault. Will use her again.”
John D.
“John took excellent care of Ginger for a few days over the Thanksgiving holiday. She does have a bit of separation anxiety but he made sure she got plenty of attention. Sent us pictures and reports throughout her visit.”
Virginia K.
“Virginia met us at a local park so we could introduce our shepherd to her before her stay. We talked for almost an hour.... it was wonderful and Virginia is amazing with people as well as dogs. She sent us pictures of our Maggie while we were away to keep us updated on how she was doing. I definitely would use Virginia again in the future and recommend her to anyone needing a loving caretaker for their pet when they are away.”
Casey W.Star Sitter
“We loved Casey and her little family. Copper was well taken care of and had fun with the dogs that were there. Glad he could have vacation while we did!”
Marlin H.
“Marlin is extremely dependable! He has cared for our cats for years; since he was a small child. He provides a lot of love to each pet. One of our cats has some serious medical issues which he has dealt with wonderfully. I know he is just as competent and caring with dogs. He has had a key to our house for years. We have complete confidence in Marlin.”
Xander B.
“My dog looked well cared for when I picked her up. Xander sent me photos of my dog enjoying herself while I was gone. I would definitely consider him again if I needed a dog sitter.”
Aurora B.
“There's no one better to leave your animals with than Aurora, she's always had pets and is very dependable. She has a dog herself who she takes to the dog park every day and always interacts with every dog there and has never met an animal she didn't like.”
Nicole O.
“Nicole is amazing! She takes Nova on walks and to the dog park. She takes very good care of my baby Nova. She even offers to do pick up and drop off for your pet. I would recommend her to anyone :)”
Keyona R.
About: I’ve taken care of my families dogs since I was a little girl. I would feed them, take them outside, and go for walks with them. Im currently working part time, so I have plenty of time to play & care for your fur babies! My schedule is pretty flexible to fit everyone’s needs. I live in a house with my children. I don’t have a fenced in yard, so I can crate or put your dog on a leash so they can have outside time.
Benjamin B.
“Benjamin has a special connections to dogs. He is kind, calm, and patient. He has watched my spoiled dog during my longer vacations. My dog loved it.”
Beth C.
“Very grateful for Beth's excellent care of my two dogs. I always get so nervous leaving my pets but I was very at ease with Beth. She sent videos of my puppers enjoying their treats while I was away. I will definitely use her again and would recommend her to anyone that need a great pet sitter!”
Kristina B.
“Kristina is great with all animals and loves them all especially her pups they are very well taken care of and so cute I would let her watch my pup anytime”
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 dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. 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
As of Aug 2025, 21 sitters provided dog boarding in Winchester. 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, 83% of Winchester dog boarding sitters respond in under an hour.
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 Winchester.
Rover makes it easy to find Winchester 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 21 dog boarding sitters in Winchester 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.
Connect anywhere with the Rover app
