Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 11 pet parents in Winchester have booked doggy day care
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.
“We left our two small dogs with Della for a few hours while we were doing a local tour on vacation. She said she took them out often, she was friendly, and they seemed very comfortable approaching her. She was waiting with them outside when we drove up to pick them up and both dogs were smiling! - that told me with the looks on their faces that they were comfortable, well cared for, and also happy and having fun. I would most definitely recommend her! And I’m very grateful that she was able to do this for us!”
“Kristen was wonderful! She had great communication prior and during the stay, and I would definitely recommend her to watch your dog. She greeted us outside when we arrived and again when we picked up our dog, which made everything feel very welcoming and personal. Our dog was well cared for, and we would absolutely use her again if we need another pet sitter. Thank you, Kristen!”
“She kept me updated the entire time which I did love. I wasn't a huge fan of the company/loud music going off which can make him a little nervous when I picked him up but overall not a bad experience.”
About: I’ve owned dogs for my entire life. I am currently a breeder. Loving and caring for dogs is my passion and I treat every dog like they are part of my family. I am a retired teacher who spends my days loving and caring for my fur babies. Pet care is a natural part of my daily routine and I am blessed to be able to give them the attention, playtime, and comfort they deserve. I offer loving pet care through both in-home and convenient drop-in visits. With years of experience raising cats and dogs, I provide a safe, comfortable, and affectionate environment, making sure your furry family members are happy and well cared for while you are away.
“Quill had a blast with Christina! He’s usually very nervous but Christina took the time to make him feel comfortable and that’s the best thing you can ask for with someone watching your dog. I would 100% book with her again.”
About: I have a big heart for taking care of dogs of all shapes and sizes. Even special needs dogs. (I have one that has seizures). If your dog needs a little training I will be happy to help. I am good with grooming. Prayers forbid I should need to use it but i am good with first aid too. I once was a CNA and was trained in CPR too. I let the licence go because I realized I wanted take care of animals, mostly dogs, not humans. I want to follow my heart and feel happy with my life. Dogs are special creatures and should be treated as such. I will even do vet trips for you if needed. I am available almost every day all day except the rare doctor appointment days.
About: I've always been a dog person. I take care all of my family and friends dogs when they leave town. Familiar with dog training and nutrition. I work remotely and have freedom to walk, feed, and pay attention to your dogs as needed. I love dogs and enjoy helping them feel at ease. Pets can cuddle on ample dog beds and couches. I lost my dog a few years back and I just kept all her stuff set up. Your dogs will have free reign of backyard and house as long as they are well behaved.
About: I have fostered over 250 amazing dogs, mostly seniors and special needs, so I have experience with most any medical or behavioral care. I have had dogs ages newborn to 16+ in my care, so I have experience with all the life stages. I have experience training dogs of all sizes, from 5 pounds to 150 pounds. I believe that my calming presence around animals set me apart to earn their trust. I am home nearly 24/7 and spend most of that with my personal pets or farm animals, so being with your pet would just be added into my routine. I have a fenced in yard. While my small inside dogs are very friendly, I am comfortable with separating if needed using crates or gates. My inside dogs are 10 pounds and under. Pets have access to all areas of my home, with supervision.
About: I used to foster for a rescue and I have taken care of dogs and cats of all sizes and ages. I am good with pets with medically and physically extra needs. I can also help train your dog while caring for them. I am available everyday to watch your pets. I treat pets like family and will also give them the highest level of care and lots of snuggles. I will take very good care of your pets and treat them like royalties. Currently I have a 1 year old cat who thinks she is a queen. And three dogs too
About: Loving home and pet owner myself, excited about welcoming your pet into our home and family. My husband and I have over 40 years of experience caring and loving for dogs. We currently have a furry friend for your loved one to play with and little ones that will keep them loved and active. I am a stay at home mom with two boys, so pet care is the perfect fit for our lifestyle and gives me the ability to be home and interact with your loved when you cannot. Our home has a fully fenced back yard for your loved one to play and take potty breaks often. The main area of the home is open to your loved one to play, snack and lounge around. We don’t like to keep animals unattended in the back yard so feel safe knowing that they will be warm in the winter and cool in the summer with the rest of the family.
The median cost per day for doggy day care in Winchester is $30
Dog parents share their Rover experiences - Winchester
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?
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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 sitter has to cancel, we’ll work with you to find a new sitter.
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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!FAQs for Doggy Day Care - Winchester
Frequently asked questions about Rover
The average cost for Doggy Day Care in Winchester on Rover is $38.15 per day (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Doggy Day Care easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Doggy Day Care. For more information on service fees, click here .
As of June 2026, there are 36 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 TN 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 36 sitters in Winchester, 87% 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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