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

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester doggy day care sitters
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Karina was absolutely wonderful to work with. Everything was super clear and she took wonderful care of our fur baby. I felt confident and at ease the whole time. She has a lot of care and compassion for animals and its clearly evident by how she interacts with them. Our pup was happy as could be when I picked him up. I would highly recommend Karina!”

About: I’ve taken care of dogs on and off for years and I’ve had a couple of my own. Would be happy to host your pet for a day or a few days, whatever your need is. I am fully retired at this time and will have plenty of time to play with and care for your pet. I am available weekdays and nights as well as some weekends. I am also available to watch them at your house as well if you’d prefer. I am happy to follow your feeding schedule and to take your pet for a daily walk. There are no young children or anyone else living in the house except me.
“Our pups Maggie and Finn had a wonderful day playing with other pups and getting a lot of activity. They were well taken care of by Cruz and her family. I knew they were in good hands.”

About: We’ve been dog sitting and caring for pets for years and have built strong relationships with dozens of happy, reliable clients. Our goal is to make every dog and cat feel comfortable, safe, loved, and anxiety-free while you’re away. We have experience with high-energy, needy, and attention-seeking pets, and we always adapt to each animal’s personality and routine. Communication is very important to us, so you can expect regular updates, photos, and peace of mind knowing your pets are being cared for like family. I’m currently home full-time with my two boys, which gives me a very flexible and reliable schedule for pet care. I’m available for walks, drop-ins, boarding, and whatever your pet may need throughout the day. Because I’m home often, your pets will receive plenty of attention, care, supervision, and companionship instead of being left alone for long periods. I’m happy to work with your pet’s routine to help them feel comfortable, safe, and right at home. We have a very large private backyard with over an acre of space for dogs to enjoy and explore. While the yard is not fenced in, it is set far back from busy roads and offers a quiet, safe, and peaceful environment. Safety is extremely important to us, and all outdoor time is closely supervised. Our property is long and spacious with plenty of room for walks, playtime, and exercise while still maintaining privacy and a calm atmosphere for pets to feel comfortable and relaxed.
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.
About: I’ve been take care of dogs since I was 18 family love me Iam very good at what I do Iam very Passionate about dogs Iam also a dog training as well for 34 years I will travel to pick up your pets if I needed Anytime Iam available no matter what time or hour always available I love what I did it make me happy about what I do I love it I take good care of the dogs I make sure they are love & safe at all times no matter what your dog will be in good hands
“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!”

“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.”

“Adrienne was Roo’s best friend for a day, and was everything I was looking for and more. Roo had a day full of adventures, and Adrienne sent us plenty of photos! We will definitely be return customers. Highly recommended!!”

“Left my baby for a trial stay. While it was hard to leave him literally crying Katie was so great about assuring me things had calmed down a few minutes later and all was good. I appreciated that peace of mind. Katie was also great about super responsive and timely communication. We would definitely reach out again.”

“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!”

About: I grew up taking care of my dog Waggles for 15 years. Have had other dogs and have taken care of friends dogs as well. Could help during the week and on weekends anytime. Happy to walk, care for and house pets overnight. Lots of love for cats and dogs. Our last cat was an indoor cat, but we have had outdoor ones as well. Happy to walk and play with dogs inside and out.
“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 !”

“Amazing Dog Sitter! I can't say enough good things about Estelle! They took such great care of my energetic puppy and made sure he was happy, well-exercised, and loved while I was away. I got regular updates and photos, which gave me so much peace of mind. It was clear that my pup was having a great time and being treated like part of the family. I highly recommend her to anyone looking for a responsible, caring, and attentive sitter. Will definitely be booking again!”

About: I see dogs as part of the family, not as just a pet, and will care for yours as if s/he were my own. Further, because your dog relies on me , I believe firmly in keeping appointments as promised, and will show up on time, every time; I will not let your furbaby down. Being retired, I am available during the weekdays and look forward to the opportunity to care for and entertain your pet. It is important to me that your dog gets a break in the middle of the day, while s/he waits for you to come home to them. My home is your pet’s home, they’ll be welcomed as one of the family. I live in a nice neighborhood with plenty of room for leashed walks
“MJ was absolutely wonderful with my pup! She kept me updated and sent the cutest pictures, which gave me so much peace of mind. My pup was so excited to see her again the very next day, she truly couldn’t wait to go back! I highly recommend MJ to anyone looking for loving and reliable care.”

“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.”

“I used Vanessa for the first time on Thanksgiving. She took really good care of little Milo. He can be shy, but he was very comfortable with Vanessa. I will definitely use her again.”


About: Hello and thank you for considering our services. Please take a moment to read our full profile, including important notes at the end. We are back to boarding pups after taking a few years off, but we are still just as dedicated to providing top notch pet care as we were when we started. Brief summary of what you can expect: We offer outside playtime morning, afternoon and night, frequent access to our large fenced in back yard, LOTS of hugs and kisses for all fur children and the occasional treat as well. Your pup will have free run or our home, sleep where they want and be treated as part of the family, which means they will be spoiled! However, we also respect any restrictions you have set so simply let us know. To help determine if your pup is a good fit. please note: - WE DO NOT TAKE AGGRESSIVE dogs under any circumstances - Unfortunately, we no longer take special needs dogs suffering from incontinence, sight or hearing impairments - We do not provide 24/7 coverage during weekdays and dogs may be left alone for roughly 4 hours a couple times during the week - All dogs must be able to navigate stairs to gain access to the backyard - We aim to be flexible with drop off & pick up times on weekends, but during the week hours are from 2:00 to 7:00 PM We are pet parents 24 hours and include the pets in all our activities. Thank you for considering trusting us with your pup ! Alan & Luis One of us works from home so typically there is someone home all day with our pups. Of course we leave to run errands and such, but our life revolves around our dogs.
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works

1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter 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!
The median cost per day for doggy day care in Winchester is $40
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
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 2026 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 2026, 168 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, 87% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 20 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 168 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.

