Dog Boarding in Winchester, OK
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Top rated Winchester dog boarders
“First time leaving my pups with Courtney and they were cared for very well! She has a great setup for dogs. I felt very reassured that they'd have a good and safe time and when I picked them up they were happy, so I was too! Thank you Courtney!”
“We have used Leah several times for our aging dog. We have been delighted how she goes over and beyond satisfying the needs of Gracie and for us. Don’t hesitate in booking her for your dog.”
“We love Toni!!!! Moe had the best time, he may have enjoyed his vacation more than we enjoyed ours! ? He received constant attention, daily walks, and was completely spoiled! We will definitely book with her again!”
“Kameryn was awesome! Her home is clean and dog friendly. She was very accommodating to Theo’s specific needs and made him feel at home while we were away. Highly recommend!”
“Perry had a great time snuggling with Ashley and Ryan! He likes being an only child and they spoiled him. They made me feel comfortable and were very fast with responding.”
“This was my Goldador's first time to stay in someone's home & she LOVED it! I know that Brent played with her & loved on her because she came home calm & content. Brent communicated with us every day & sent a few pics. In every pic she looked happy & was having fun. We will definitely be booking with Brent again!”
“I definitely will book her again ❤️She was very nice and communication was perfect 🤩 She sent messages and photos thru the day loved that she had a little one cause my dog loves kids 🥰Don’t just look book her you want be disappointed 💕”
“Lynsi was Great with my Golden Retriever Pup! She worked a bit on the training she still needs and kept me in the loop! My girl was happy and healthy when I picked her up. Thank you!”
“Theo has now stayed with Evette multiple times and she is always communicative and helpful! He clearly loves it there and is so well cared for when we return. Would recommend to anyone!”
“Gracie was an exceptional host to our boy murph! She has an adorable golden retriever who ours was in love with lol. She sent updates and photos as frequently as we desired & it was great to see his face on our vacation. I def recommend booking with Gracie & fergie ❤️”
“Lauren did a fantastic job taking care of our pups over a long weekend. She also sent plenty of pictures of them being cute and having a great time. I’d highly recommend her as an excellent Rover pet sitter!”
“Thank you so much Judy and Eric for taking care of our little fur. Thank you for the gift you two got for him. He loved it. Thank you for spoiling him with love. We would definitely book again with Judy. ❤️❤️”
“Sonya took great care of Bella and she really enjoyed her stay there! She was easy to contact and kept me updated with cute pics and everything else. I would gladly use her services again in the future!”
“Marta was incredible! We were very confident our girl would be in great hands. She went above and beyond to make sure our dog felt comfortable with her and we couldn’t be more grateful! Lots of pics and updates as well 😊 would 100% recommend!!”
“Donna was amazing. Very kind personality and willing to accommodate Wallie's special diet and my delayed return. I will feel very comfortable leaving Wallie with Donna in the future. Her two senior dogs were very sweet and let Wallie blend in right away.”
Loving dog boarding sitters in your neighborhood
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Courtney B.
Star Sitter
“First time leaving my pups with Courtney and they were cared for very well! She has a great setup for dogs. I felt very reassured that they'd have a good and safe time and when I picked them up they were happy, so I was too! Thank you Courtney!”
Leah R.Star Sitter
“We have used Leah several times for our aging dog. We have been delighted how she goes over and beyond satisfying the needs of Gracie and for us. Don’t hesitate in booking her for your dog.”
Toni W.Star Sitter
“We love Toni!!!! Moe had the best time, he may have enjoyed his vacation more than we enjoyed ours! ? He received constant attention, daily walks, and was completely spoiled! We will definitely book with her again!”
Kameryn C.Star Sitter
“Kameryn was awesome! Her home is clean and dog friendly. She was very accommodating to Theo’s specific needs and made him feel at home while we were away. Highly recommend!”
Aleacia C.Star Sitter
“She did great with our 1 year old German shepherd that has terrible separation anxiety! Pictures, videos, and updates while we were gone! Will definitely use again!”
Erin P.Star Sitter
“Erin took such good care of Whiskers! She said that he loved running in her yard and she took him for a walk. He's requested to go back to see her again soon!”
Ashley & Ryan H.Star Sitter
“Perry had a great time snuggling with Ashley and Ryan! He likes being an only child and they spoiled him. They made me feel comfortable and were very fast with responding.”
Brent S.Star Sitter
“This was my Goldador's first time to stay in someone's home & she LOVED it! I know that Brent played with her & loved on her because she came home calm & content. Brent communicated with us every day & sent a few pics. In every pic she looked happy & was having fun. We will definitely be booking with Brent again!”
Stasia H.Star Sitter
“Stasia was absolutely lovely to work with. She took excellent care of our dogs and is super kind. We will for sure use her as a sitter again!”
Cait C.
“I definitely will book her again ❤️She was very nice and communication was perfect 🤩 She sent messages and photos thru the day loved that she had a little one cause my dog loves kids 🥰Don’t just look book her you want be disappointed 💕”
Lynsi K.Star Sitter
“Lynsi was Great with my Golden Retriever Pup! She worked a bit on the training she still needs and kept me in the loop! My girl was happy and healthy when I picked her up. Thank you!”
Evette A.Star Sitter
“Theo has now stayed with Evette multiple times and she is always communicative and helpful! He clearly loves it there and is so well cared for when we return. Would recommend to anyone!”
Gracie M.Star Sitter
“Gracie was an exceptional host to our boy murph! She has an adorable golden retriever who ours was in love with lol. She sent updates and photos as frequently as we desired & it was great to see his face on our vacation. I def recommend booking with Gracie & fergie ❤️”
Lauren G.Star Sitter
“Lauren did a fantastic job taking care of our pups over a long weekend. She also sent plenty of pictures of them being cute and having a great time. I’d highly recommend her as an excellent Rover pet sitter!”
Judy B.
“Thank you so much Judy and Eric for taking care of our little fur. Thank you for the gift you two got for him. He loved it. Thank you for spoiling him with love. We would definitely book again with Judy. ❤️❤️”
Sonya N.
“Sonya took great care of Bella and she really enjoyed her stay there! She was easy to contact and kept me updated with cute pics and everything else. I would gladly use her services again in the future!”
Marta Ines D.
“Marta was incredible! We were very confident our girl would be in great hands. She went above and beyond to make sure our dog felt comfortable with her and we couldn’t be more grateful! Lots of pics and updates as well 😊 would 100% recommend!!”
Donna S.Star Sitter
“Donna was amazing. Very kind personality and willing to accommodate Wallie's special diet and my delayed return. I will feel very comfortable leaving Wallie with Donna in the future. Her two senior dogs were very sweet and let Wallie blend in right away.”
Carson P.
“Carson was great and went over and above expectations. He even took our dog to the vet during our time away. He communicated well and cared for our dog in the best way.”
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?
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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.
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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, 236 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, 94% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 10 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 236 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 97% of sitters offer daily exercise, 97% offer medication administration, and 88% 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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