Doggy Day Care in Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Winchester doggy day care sitters

“Ziggy had a great time spending the day with Jaylese for doggy daycare! They went on a nice walk and Ziggy came back happy and sleepy. She accepted my request last minute and was a breeze to work with - highly reccomend!”


“Amber was great with Ollie while I had to do something during the day. Took photos and kept a good eye on Ollie while I was gone. She was flexible and communicative. Highly recommend and would use again if in the are”


“Excellent service, was sent great pictures of Sadie and she was happy. Very accommodating. We Will use Fiona again for sure.”


About: Grew up on a farm caring for animals since my youth. now enjoy the company of visiting dogs, just like I had with my own. I currently work part-time and many situations able to bring a boarding dog with me; as I work with mostly older folks who would love the sweetness of a dog visit; considered therapy. I have a side fenced yard, safe from the road, and only do private walks in a comfortable grass field near my home, leashed and one at a time for individual attention.

“This was the first time that I used Eric. Eric and his wife were wonderful with Milo. Eric let me know that Milo was doing well and also sent a picture. Milo came home happy and tired. I will definitely use Eric again.”


“Katie was so awesome with our puppy. She was incredibly flexible. Will definitely use her services again.”


“Rockie had a wonderful time playing chase with her new doggie friends in the back yard and came home a tired and happy pup after a wonderful day with Khanh and Tommie, She will stay with them again!”


“Our first time having MJ take care of our puppy. She loves dogs and gave our dog some quality time while we were away. We will call on her again.”


“Our dog Rocky loves to go to Maria’s house. Everyday Rocky runs up the steps and can’t wait to go inside. He has a great time playing with other dogs. Maria is flexible and accommodating. There were nights that we couldn’t pick up Rocky until late and she was always accommodating and flexible. I can tell that she really love dogs! We had a great experience with her and very thankful of her watching Rocky.”


“Karina was WONDERFUL! Our dog hasn’t been boarded a lot in her life, and has been nervous when she has, but she was comfortable as soon as we walked into the yard and so calm and happy when we picked her up! Karina was so communicative before and during her stay, and I appreciate how through she was with what to bring and making sure all the dogs in her care are up to date on vaccinations. We are so happy with our stay and will definitely bring our dog back!”


“Gail is a dream! She kept my girl active and engaged and shared pictures as well. I had total peace of mind leaving my pup with her. She is also a great communicator. Highly recommend.”


“Super easy drop off and pick up for my two cats, and they had a nice little time. She sent photos and kept me updated and made everything easy ????.”


“Katrini and Potter have been an incredible addition to our puppy’s day! He is so excited to go to day care every single time we drop him off. Potter has an incredible temperament and is an excellent play partner while Katrini is an amazing communicator and always goes the extra mile. Leaving your puppy with someone is always hard but Katrini and Potter make it so easy. I couldn’t recommend them enough!”


“Briana was very kind and available for my puppy. I believe Molly was very happy in her care and was given enough attention. I will definitely use Briana again in the future as needed.”


About: Hi there! I'm Ashley, a lifelong dog lover and work-from-home mom ready to give your pup the care and comfort they deserve. I have a special place in my heart for senior dogs, especially after caring for my fur daughter, my sweet long-haired Chihuahua who was by my side for 17 wonderful years. I understand the slower pace and extra TLC that older pups need, and I’m here to provide just that. We’ve also had two German Shepherd mixes in the past, so I’m no stranger to larger breeds. While I typically prefer small to medium-sized dogs for our home setup, I’m open to exceptions for well-mannered larger dogs — especially seniors. Because I work from home and my kids are at daycare during the day, it’s just me and your pup…which means plenty of calm, one-on-one attention and companionship in a quiet environment. I know how stressful it can be to find care you trust…especially when options in our area are limited. That’s why I treat every dog like family, with love, routine, and lots of affection. I’ll care for your furry loved one as if they were my own and will happily share updates and photos as often as you'd like to give you peace of mind while you're away. I provide attentive, loving care while fitting seamlessly into my daily routine. Because I work from home with a lot of flexibility, I can offer daily daycare with plenty of walks, playtime, and cuddles. I’m also happy to provide overnight boarding for dogs who need a home-away-from-home. Throughout, I’ll keep you updated as much as you’d like, so you always feel comfortable and connected. I care for dogs in a safe, comfortable home environment where your dog will be treated like a valued family member. While I don’t have a fenced backyard, your dog will always be supervised and safe. They’re always free to explore and relax throughout the home. Because pets are part of the family, we often allow them on the couch and beds to snuggle and feel at home, but I’m always happy to follow your preferences to make sure your fur baby feels comfortable and loved.

“Nell is wonderful. Super flexible with arranging time to drop off and pick up. Dizzy loves staying here. He would run down the steps to the front door! I would definitely recommend her for any pet care needs !”


“Angela was great! Phoebe is always a little sad and anxious away from home and Angeka really helped her settle in. She has a wonderful kindness that the animals really connect with..Phoebe really liked her from the very first. Will definitely use her again for our next weekend away”


About: As someone who has taken care of animals for almost two decades, I've seen it all. From aggressive pets, to escapists, to pets with serious health problems. But even with those hardships I've managed to get through for those dogs and their owners. I've met some very amazing animals throughout my years, and everytime they can't get enough of me, I'm basically the Pet Whisper. And I'm always able to complete the checklist, feed, walk, take them to their appointments, and so on. My clients have been able to trust me, I'm a hard worker who doesn't give up, who goes above and beyond to make my clients proud and their pets happy. I'm currently employed as a Sales Associate at Ocean State. My hours vary quite a bit, but normally I work up to 3 weekdays and both weekends, sometimes only one of them. My hours can be from 7-1 to 11 or 1-7:30 Currently I have a dog and cat. My cat stays in my room while my dog is allowed in our stairway, hallway, living room, dining room and kitchen. My cat gets along with all cats, but is very finicky around other dogs, even my own. They are both separated by a gate, so there's no fear of them ever interacting as my dog loves trying to chase her if he ever gets the chance. My dog gets along with most dogs regardless of size but, he'll always be egging them on to play haha. My house isn't entirely large but it's enough for your pet to move around, play, and relax. My complex is very large and a great walking area for your pet. There's also a dog park right around the street that's a wonderful place for your dog to socialize. And, next to that park is a large trail that's perfect for walking. If your dog likes the beach, there's plenty of them in my vicinity.


“Our young pup Hank spent the day with Rich and his three dogs. Hank had an amazing day running around Rich’s awesome backyard. Rich was so attentive, made sure to work on the commands we’ve been training, sent lots of updates, and really went above and beyond taking care of him. We can’t wait for Hank to keep going back :)”


“Sam had the best day ever with Rebecca and we felt comfortable knowing he was with her. She was great at communicating with us throughout the day and sending pictures. He will definitely be back for more fun.”

Loving doggy day care in your neighborhood
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Jaylese H.Star Sitter

“Ziggy had a great time spending the day with Jaylese for doggy daycare! They went on a nice walk and Ziggy came back happy and sleepy. She accepted my request last minute and was a breeze to work with - highly reccomend!”


Amber B.

“Amber was great with Ollie while I had to do something during the day. Took photos and kept a good eye on Ollie while I was gone. She was flexible and communicative. Highly recommend and would use again if in the are”


Fiona O.Star Sitter

“Excellent service, was sent great pictures of Sadie and she was happy. Very accommodating. We Will use Fiona again for sure.”


Mary Ann P.Star Sitter
“Mary Ann has had dogs all her life. She has a loving and caring personality that comes across in all her interactions with others. I'm a two year ROVER sitter and she is very familiar with how it works. I assure everyone she would be a great hostess for your loved pets.”


Eric L.Star Sitter

“This was the first time that I used Eric. Eric and his wife were wonderful with Milo. Eric let me know that Milo was doing well and also sent a picture. Milo came home happy and tired. I will definitely use Eric again.”


Katie L.Star Sitter

“Katie was so awesome with our puppy. She was incredibly flexible. Will definitely use her services again.”


Angela & Tommy P.

“Rockie had a wonderful time playing chase with her new doggie friends in the back yard and came home a tired and happy pup after a wonderful day with Khanh and Tommie, She will stay with them again!”


MJ M.Star Sitter

“Our first time having MJ take care of our puppy. She loves dogs and gave our dog some quality time while we were away. We will call on her again.”


Cruz Maria D.Star Sitter

“Our dog Rocky loves to go to Maria’s house. Everyday Rocky runs up the steps and can’t wait to go inside. He has a great time playing with other dogs. Maria is flexible and accommodating. There were nights that we couldn’t pick up Rocky until late and she was always accommodating and flexible. I can tell that she really love dogs! We had a great experience with her and very thankful of her watching Rocky.”


Karina S.
Star Sitter


“Karina was WONDERFUL! Our dog hasn’t been boarded a lot in her life, and has been nervous when she has, but she was comfortable as soon as we walked into the yard and so calm and happy when we picked her up! Karina was so communicative before and during her stay, and I appreciate how through she was with what to bring and making sure all the dogs in her care are up to date on vaccinations. We are so happy with our stay and will definitely bring our dog back!”


Gail S.

“Gail is a dream! She kept my girl active and engaged and shared pictures as well. I had total peace of mind leaving my pup with her. She is also a great communicator. Highly recommend.”


Kimberlly C.

“Super easy drop off and pick up for my two cats, and they had a nice little time. She sent photos and kept me updated and made everything easy ????.”


Katrini L.Star Sitter

“Katrini and Potter have been an incredible addition to our puppy’s day! He is so excited to go to day care every single time we drop him off. Potter has an incredible temperament and is an excellent play partner while Katrini is an amazing communicator and always goes the extra mile. Leaving your puppy with someone is always hard but Katrini and Potter make it so easy. I couldn’t recommend them enough!”


Briana V.

“Briana was very kind and available for my puppy. I believe Molly was very happy in her care and was given enough attention. I will definitely use Briana again in the future as needed.”


Ashley D.
“Ashley is the definition of a true dog lover. I have known her for 15 years and would highly recommend her as a pet sitter. She is caring, responsible and your pet would be in good hands with her!”


Nell S.Star Sitter

“Nell is wonderful. Super flexible with arranging time to drop off and pick up. Dizzy loves staying here. He would run down the steps to the front door! I would definitely recommend her for any pet care needs !”


Angela W.

“Angela was great! Phoebe is always a little sad and anxious away from home and Angeka really helped her settle in. She has a wonderful kindness that the animals really connect with..Phoebe really liked her from the very first. Will definitely use her again for our next weekend away”


Matt T.
“He will be there to take care of that pats every need and make sure he can be trusted to do said job. He’s a very trustworthy person and he’s so reliable if I could hire anyone to take care of pets it would be him.”




Richard W.

“Our young pup Hank spent the day with Rich and his three dogs. Hank had an amazing day running around Rich’s awesome backyard. Rich was so attentive, made sure to work on the commands we’ve been training, sent lots of updates, and really went above and beyond taking care of him. We can’t wait for Hank to keep going back :)”


Rebecca P.

“Sam had the best day ever with Rebecca and we felt comfortable knowing he was with her. She was great at communicating with us throughout the day and sending pictures. He will definitely be back for more fun.”
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1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter 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 day for doggy day care in Winchester is $40
Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 5 repeat doggy day care clients
Doggy Day Care FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winchester on Rover as of Jun 2025 was about $40 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2025, 188 sitters provided doggy day care in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care 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 Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 19 years of experience. Sitters offering doggy day care with repeat customers have an average of 5 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.
Winchester doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winchester sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
There are 188 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 94% of sitters offer daily exercise, 100% offer medication administration, and 100% 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 doggy day care 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 doggy day care 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
