Dog Boarding in Winchester, MO
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Top rated Winchester dog boarders
“Frudo had a fun time staying at Misty’s place. In all the pictures he looked happy and excited and bonded really well with Appa. Frudo is just looking forward to his next vacation at Misty’s.”
“Can't recommend Elisabeth enough! She is the best sitter I could ask for. I'm so thankful to have found her and can now enjoy a vacation knowing my baby is in GREAT hands.”
“Lorri was an exceptional dog sitter! She provided excellent care for my corgi-bulldog mix, and it's evident that my furry friend had a fantastic stay because she returned home even happier than ever. A huge thank you once again for taking such wonderful care of my beloved pet!”
“As usual Alycia provided excellent care for my dog while I was away. Great communication and lots of pictures/video. Already have another booking with Alycia in the coming weeks. Would highly recommend.”
“Susan took excellent care of my fur baby. She sent many pictures during my vacation which put me at ease. When I picked him up he was clean, brushed, happy and well fed. I will definitely contact Susan again.”
“We are SO grateful that we found Bhairavi on Rover! Her and her family took amazing care of our dog, Frank. We received the perfect amount of updates during his stay and it was so clear he was well taken care of and so loved on. We couldn’t recommend her more and she will be the first person we contact for help with Frank moving forward!”
“Dawn was so awesome sending me photos and updates. She clearly loves animals and is very professional and nice. Her dog is really sweet. My dog was a total jerk the whole time and peed and pooped in her house and she was really nice about it. I felt so bad! Highly recommend.”
“Haley took great care of our dog Darwin and even provided updates and photos throughout the weekend! Everything went smoothly and we will definitely use her again in the future!!”
“Raina is extremely responsive! Her backyard has a high fence and was perfect for my sun-loving dog. You’ll receive photos and videos to assure your pup is happy and moving. Her cat Oreo is great with dogs! It was my dog’s first time being at a place with a cat and it went great. Raina is attentive and she will take great care of your pup!”
“We have left our almost 15 year old poodle, Peaches, with Carly and Doug several times. Most recently, we left her there while we were traveling out of the country for 9 days. Everything went great!! They treat Peaches just like family! We are very comfortable leaving her with them and will definitely be contacting them again for future visits!!”
“Donna provided excellent care of Jasper. She sent photos and regularly updated on how he was doing. I could tell from the photos that he was enjoying his stay. I highly recommend her and plan to book again when needed.”
“Kathryn was great! She took care of our 6month old puppy while we were out of town and did such a great job! I felt very comfortable leaving our puppy with Kathryn and her family after the initial meet and greet. She put me at ease immediately by answering all my questions and I could tell she is a true animal lover. We received daily updates with pictures and videos and she was very responsive to my texts. I would highly recommend Kathryn and we will definitely be using her services again in the future.”
“Anusha and her family have been amazing with my Ollie bear, they have sent daily updates of how Ollie was doing including with playful photos. I would definitely leave my dog with Anusha and her wonderful family again. Thank you Anusha for everything you’ve done for my Ollie bear!”
“Na and Gary are amazing! Marlon had the best time running around the back yard and hanging out with them. Will absolutely use them again to watch my guy! Thank you Na and Gary.”
Loving dog boarding sitters in your neighborhood
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Misty S.
Star Sitter
“Frudo had a fun time staying at Misty’s place. In all the pictures he looked happy and excited and bonded really well with Appa. Frudo is just looking forward to his next vacation at Misty’s.”
Elisabeth L.Star Sitter
“Can't recommend Elisabeth enough! She is the best sitter I could ask for. I'm so thankful to have found her and can now enjoy a vacation knowing my baby is in GREAT hands.”
Lorri M.Star Sitter
“Lorri was an exceptional dog sitter! She provided excellent care for my corgi-bulldog mix, and it's evident that my furry friend had a fantastic stay because she returned home even happier than ever. A huge thank you once again for taking such wonderful care of my beloved pet!”
Alycia H.Star Sitter
“As usual Alycia provided excellent care for my dog while I was away. Great communication and lots of pictures/video. Already have another booking with Alycia in the coming weeks. Would highly recommend.”
Nicole & Brian F.
“Nicole and Brian provided amazing service for our dog. They were very knowledgeable and capable of handling my pets unique needs. Highly recommend!”
Susan K.Star Sitter
“Susan took excellent care of my fur baby. She sent many pictures during my vacation which put me at ease. When I picked him up he was clean, brushed, happy and well fed. I will definitely contact Susan again.”
Bhairavi K.
“We are SO grateful that we found Bhairavi on Rover! Her and her family took amazing care of our dog, Frank. We received the perfect amount of updates during his stay and it was so clear he was well taken care of and so loved on. We couldn’t recommend her more and she will be the first person we contact for help with Frank moving forward!”
Jeanne G.Star Sitter
“Jeanne sent regular picture of my dog Zoe playing outside and interacting with the other dogs. I would use Jeanne again. Thank you for taking care of my Zoe!”
Dawn G.Star Sitter
“Dawn was so awesome sending me photos and updates. She clearly loves animals and is very professional and nice. Her dog is really sweet. My dog was a total jerk the whole time and peed and pooped in her house and she was really nice about it. I felt so bad! Highly recommend.”
Beth P.Star Sitter
“Lucy always has a great time and is well cared for when she stays with Beth. She has lots of playtime with other pups and cuddles on the couch.”
Haley C.Star Sitter
“Haley took great care of our dog Darwin and even provided updates and photos throughout the weekend! Everything went smoothly and we will definitely use her again in the future!!”
Raina G.Star Sitter
“Raina is extremely responsive! Her backyard has a high fence and was perfect for my sun-loving dog. You’ll receive photos and videos to assure your pup is happy and moving. Her cat Oreo is great with dogs! It was my dog’s first time being at a place with a cat and it went great. Raina is attentive and she will take great care of your pup!”
Carly & Doug B.Star Sitter
“We have left our almost 15 year old poodle, Peaches, with Carly and Doug several times. Most recently, we left her there while we were traveling out of the country for 9 days. Everything went great!! They treat Peaches just like family! We are very comfortable leaving her with them and will definitely be contacting them again for future visits!!”
Tzu C.
“Donna provided excellent care of Jasper. She sent photos and regularly updated on how he was doing. I could tell from the photos that he was enjoying his stay. I highly recommend her and plan to book again when needed.”
Alicia S.Star Sitter
“Alicia and family were fantastic hosts and took loving care of our dog while we were out of time. She’s now our go-to sitter to take care of our dog!”
Kathryn V.Star Sitter
“Kathryn was great! She took care of our 6month old puppy while we were out of town and did such a great job! I felt very comfortable leaving our puppy with Kathryn and her family after the initial meet and greet. She put me at ease immediately by answering all my questions and I could tell she is a true animal lover. We received daily updates with pictures and videos and she was very responsive to my texts. I would highly recommend Kathryn and we will definitely be using her services again in the future.”
Jennifier M.Star Sitter
“Jennifer and her son were great with my dog. Plenty of play time, snuggles, and pictures sent. I look forward to booking care for Gracie with Jennifer again!”
Anusha & Ananth G.
“Anusha and her family have been amazing with my Ollie bear, they have sent daily updates of how Ollie was doing including with playful photos. I would definitely leave my dog with Anusha and her wonderful family again. Thank you Anusha for everything you’ve done for my Ollie bear!”
Stephanie H.
“Stephanie loves dogs and will love your dog! She went all out for our boxer. We felt he was well taken care of and we definitely recommend Stephanie.”
Nancy & Gary L.Star Sitter
“Na and Gary are amazing! Marlon had the best time running around the back yard and hanging out with them. Will absolutely use them again to watch my guy! Thank you Na and Gary.”
Winchester dog parents share their Rover experiences
Jess was great to work with during Lucas's second stay with her and Lucas seemed very comfortable and relaxed in her home and with her dogs and family. We loved receiving the daily pics and comments on what he was up to and although we missed him terribly, we felt content that he was being well cared for and given plenty of hugs. Thank you for another great stay, Jess!
We had a great experience with Annie! She was absolutely wonderful with my dogs—they loved her. She kept me updated with messages and photos, which gave me peace of mind while we were away. Her communication was excellent, and it was clear she truly cares about the animals she watches. Highly recommend!
Jeanne is absolutely amazing. Our dog April stayed with her for a week. Jeanne sent photos throughout April’s stay / kept us up-to-date with how she was doing. We could tell through the photos how happy April was during her visit - a visit filled with lots of walks and snuggles, Aprils favorite things! Our dog has separation anxiety and we knew Jeanne took extra care of April / helped to ensure her time alone was minimal so she would be comfortable. At the end of the stay, Jeanne even left a sweet note and prints of photos of our sweet April. We love Jeanne!!!
Dawn, Brian & family provided a fun, loving and caring home for our precious Winston while we travelled to Italy for 10 days. I think Winston was a little disappointed to have to come back home with us! 😊 Really appreciated receiving daily updates and pictures while we were away. The communication was great! Would highly recommend Dawn & Brian and we will definitely use them again for Winston.
Randy is hands down the absolute best dog sitter we’ve ever had. Our little Winston had a great time and so did my husband and I while on a weekend getaway — we were comforted to know our precious boy was in such good hands. Randy sent pics, regular updates and even reached out when she noticed Winston limping (something that was normal for him but I forgot to mention). She was super attentive, loving and even took Winston for playdates with a neighbor dog which he absolutely loved. She went above and beyond to follow our instructions - even our crazy ones like special meal prep for Winston. She is s such a dog lover and really treated Winston like gold. This was our first time using Rover. She made the whole process easy for us. Thank you Randy! We will definitely seek your services again.
Popular requests near you
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1. Search
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The median cost per night for dog boarding in Winchester is $40
Why Choose Rover?
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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.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 1,009 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, 93% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 17 years of experience. Dog boarding sitters with repeat customers have an average of 13 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 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 1,009 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 89% of sitters offer daily exercise, 96% offer medication administration, and 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care 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.
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