Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Winchester, Find top rated doggy day care
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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!”
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 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.
“Maria is truly amazing and treats my puppy Bella like family. She is caring, responsible and very flexible. I highly recommend her to anyone that is looking for help.”
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: I grew up with dogs and have always loved caring for them. I currently have a mix breed, Marley who is my little sunshine. I enjoy hiking, running and watching cartoons with him haha. I know what its like finding someone who is trustworthy to care for my dog when I need to travel for work or personal vacation. It can be a bit stressful looking for a good sitter but I can assure you that your dog will be in good hands.
“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 !”
“This was our first time using Angela and was very happy with everything! Great communication! Our pup seemed happy and tired after spending the day with Angela! Love the nice fenced in yard.”
“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.”
“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: 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
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.
“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 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
“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!”
“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”
The median cost per day for doggy day care in Winchester is $40
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How Rover works
1. Search
Browse profiles of sitters near you who offer doggy day care
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 5 repeat doggy day care clients
FAQs for Doggy Day Care - Winchester
Frequently asked questions about Rover
As of July 2026, there are 432 sitters on Rover offering Doggy Day Care across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Winchester commute.
If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.
Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.
A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.
Here are tips for finding the ideal day care fit for your dog:
- For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
- For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
- For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.
Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in CT ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 432 sitters in Winchester, 88% respond to messages in under an hour.
You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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