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

“Our dogs had a blast at Nicole’s place. They got to run around in her nice fenced in yard, played a lot of fetch and got to cool off in the kiddie pool. Nicole and her family are obviously dog lovers and I was so happy we left our girls with them. I would highly recommend Nicole to care for your pups as if they were her own.”


“John was very caring and supportive to my dog who is anxious with new people. . He was also very flexible with the time, which I really appreciated. I already planned a second day for him to watch my dog.”


“Briana made me feel so at ease leaving Moose, even on short notice. He was clearly relaxed, happy, and safe in her care. The thoughtful updates and outstanding photos meant the world. We’re so grateful—and will absolutely book again!”



“My dog had the most amazing time here! Luiz is so good with dogs and my William felt right at home. He sent many pictures and videos. I haven’t seen my dog so happy since his sister pup passed. So thankful to Luiz and his family.”


“Jessica and her daughter were fabulous hosts!! First off where they live is phenomenal!! It is so green and surrounded with wilderness. Loads of beautiful hiking areas and a nice big house!! They both come across as really gentle giving kind hearted people who are great with animals!! Bruno had a great time with them and was ready to go to sleep when we got home last night!! I would definitely recommend them and plan to use them again in the future!!”


About: Hi! I’m Nico! For years, friends and family always called me first when they needed a pet sitter, the pets and I both loved it! For 15-years as a butler and personal assistant to families in NYC & LA, management of high quality pet care has been one of my favorite responsibilities! Feeling lucky to have learned from all the best celebrity dog trainers in the world! My husband Matthew and I are new-ish to Franklin County, Massachusetts, and my current local clients would gladly provide references if you wanted to hear how care I’ve provided for their furry family members! I am currently working from home, writing a book, and would love more reasons to get up, get out, walk, and have some pets in the home too! I have dog bowls, beds, toys, and a big yard backed up to the woods for fuzzy friends to enjoy! If your pooch is not great off leash, that’s ok! I also have an outdoor pen and doghouse to keep them safe while I’m outside gardening! I love to have the dogs near me at all times!

“Tamara took great care of Archie! He was very happy to spend time with her and is looking forward to returning. Archie's human parents appreciated Tam's excellent communication and the photos!”


“Letícia took great care of Juni and was very thoughtful about making sure Juni was comfortable. Letícia is very responsible and caring and capable. I will definitely be using Letícia again! Do not hesitate to book!”


“Rachael was wonderful! Opie went for a day play and hang out. He had some buddies to play with and was a sleepy pup once we got back home. Rachael sent photos and reassured us everyone was happy! Thanks!!”



“Sofie is the most amazing petsitter I have ever met. Moki and Ollie were well cared for on a very stressful house-moving-day and Sofie was a kind and generous host even as she navigated their upset tummy issues. Thank you, Sofie; we will return when the boys are feeling well and settled and less stressed out. I appreciate you wholeheartedly.”


“Had a meet and greet afternoon for Skipper and Mady was so great! Mady communicated during the stay and Skipper did well with her dog and kitty. We will be using Mady again for sure <3”


About: I've had dogs of various breeds since I was 7, and participated in competitive dog obedience and agility training in high school. I love to go on walks, and would look forward to getting to known your pet! I work from home, so I am around most if not all of the time. Our backyard is fenced and I love to take regular walks! I can care for your pet at my home or yours! Let me know your pets needs and we can find a schedule that best suits you.

About: I am dog mom of two; I have two golden retrievers and have experience working with puppies and also adapting their training skills and making sure they are stimulated. A stimulated dog, is a happy dog. I also have experience making healthy homemade cooked meals, as I feed my dogs daily a healthy home cooked diet. I currently work from work Monday- Friday but have a flexible schedule and also available for weekend work. I currently am looking for side work to maintain a busy schedule and lifestyle. I have two golden retrievers at home, Brooklyn and Belle. I will always ensure safety if a pet is brought to my home and make sure a crate is available at all times in case a pet needs space. If I travel to your home, please assure I will take all measures to make your pet comfortable and build my trust with every visit.

About: I love dogs. I have a rescue her name is Snickers and shes 7 months old. I've had dogs all my life. How anyone can hurt man's best friend is beyond me. She is like my child and makes me smile, keeps me company and I dont know what I would do without her. I love her with all my heart and wouldnt trade her for the world. I would treat anyone's dog like I would my own. They are all special in their own way. I would be honored to take care of your dog, I look forward to meeting you very soon. Thank you, Robin K I work full time at home and I'm able to walk my dog and take her out anytime! I'm available all day. My Snickers would love a play mate. I dont have crate but if yours needs one you'll have to bring it. I'm very diligent in taking my pup out all day long.

“Laura was very welcoming and I felt confident leaving my anxious dog with her. Her property is a beautiful place for animals to spend the day. We had a nice conversation at pick up and I appreciate her kindness. My dog was very comfortable with her.”

About: I work at home and have time to make sure all of your pets needs are met. I am comfortable with dog and pets of all different temperaments--- I've taken classes on canine behavior in undergrad and have a good understanding of dogs with unique needs. I have a lot of experience with cats and dogs of all ages and personalities. I have two cats who get along well with dogs. My sister and I live in a stand alone home with a large yard for animals to play in, and a lot of space in the home. Our home abuts conservation land with lots of trails for walking and playing. I would be honored to care for your animal companions, and can ensure they will be safe and happy during their time with me :) I work from home and have alot of flexibility with my job so I can ensure your animal companion will have my full attention throughout the day, including walks, and hikes if desired! Happy to board pets, large home and yard with two friendly cats. Can take your dog on walks throughout the day leashed or unleashed (depending on need). Experience with geriatric dogs and puppies alike !

About: I’m always happy to meet a new furry friend! I have a dog that I regularly spend time with (Finley, a beagle hound mix) who loves to run around our spacious back yard. There is a wonderful pond (perfect for pups taking a dip) just a 10 minute walk down our remote road. I am well practiced in house sitting and caring for animals in a relaxed and positive manner. I work part time as a waitress so my schedule is very flexible. Usually I will be able to return in time to accommodate bathroom breaks and walks. I have a very large yard with a long leashed run. I am happy to accommodate crating if that is preferred. I spend a good amount of time with a playful medium sized beagle mix if your pup would like to have a pal.
Loving doggy day care in your neighborhood
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Nicole S.Star Sitter

“Our dogs had a blast at Nicole’s place. They got to run around in her nice fenced in yard, played a lot of fetch and got to cool off in the kiddie pool. Nicole and her family are obviously dog lovers and I was so happy we left our girls with them. I would highly recommend Nicole to care for your pups as if they were her own.”


John M.Star Sitter

“John was very caring and supportive to my dog who is anxious with new people. . He was also very flexible with the time, which I really appreciated. I already planned a second day for him to watch my dog.”


Briana L.Star Sitter

“Briana made me feel so at ease leaving Moose, even on short notice. He was clearly relaxed, happy, and safe in her care. The thoughtful updates and outstanding photos meant the world. We’re so grateful—and will absolutely book again!”




Luiz B.
Star Sitter


“My dog had the most amazing time here! Luiz is so good with dogs and my William felt right at home. He sent many pictures and videos. I haven’t seen my dog so happy since his sister pup passed. So thankful to Luiz and his family.”


Jessica C.Star Sitter

“Jessica and her daughter were fabulous hosts!! First off where they live is phenomenal!! It is so green and surrounded with wilderness. Loads of beautiful hiking areas and a nice big house!! They both come across as really gentle giving kind hearted people who are great with animals!! Bruno had a great time with them and was ready to go to sleep when we got home last night!! I would definitely recommend them and plan to use them again in the future!!”


Haley C.Star Sitter

“Hayley had Féirin for the day, and after that Féirin seemed happy, healthy, and tired. She fell asleep in the car on the way home. What else can you ask for?”


Nico M.
“Nico is an absolute DREAM! Her energy is immaculate and just being around her is a gift. I literally don't trust anyone to take care of my baby and she came through with flying colors during a very difficult time! Layla, my dog (65lb female pitbull) had just gone through a very traumatic surgery and needed a lot of special care and love. Nico came to my house and stayed with her everyday for 2 weeks. Not only did Nico go above and beyond with Layla's care, she was extremely professional and 1000% trustworthy. Nico kept Layla on her strict medication schedule as well as changed the dressings on her wounds, a very tricky job that requires extreme patience and calm energy. She also sent me regular daily videos and photos and kept my anxious heart at ease. Layla is a dog reactive girl and Nico made every precaution to keep her safe and happy. Layla also loves to chase squirrels and can sometimes be a lot to handle on a walk. Nico was a complete pro at handling these sometimes difficult situation and even did some training with her during her stay. Layla and I are absolutely in love with Nico and would wholeheartedly recommend her to anyone who is lucky enough to have even just a little bit of her time. PLEASE TIP HER WELL SHE IS A GEM!!!”


Tamara M.

“Tamara took great care of Archie! He was very happy to spend time with her and is looking forward to returning. Archie's human parents appreciated Tam's excellent communication and the photos!”


Letícia B.

“Letícia took great care of Juni and was very thoughtful about making sure Juni was comfortable. Letícia is very responsible and caring and capable. I will definitely be using Letícia again! Do not hesitate to book!”


Carter M.

“Zippy seemed to have a great time! Carter did a great job with him. Thx!”


Rachael L.Star Sitter

“Rachael was wonderful! Opie went for a day play and hang out. He had some buddies to play with and was a sleepy pup once we got back home. Rachael sent photos and reassured us everyone was happy! Thanks!!”




Sofie A.


“Sofie is the most amazing petsitter I have ever met. Moki and Ollie were well cared for on a very stressful house-moving-day and Sofie was a kind and generous host even as she navigated their upset tummy issues. Thank you, Sofie; we will return when the boys are feeling well and settled and less stressed out. I appreciate you wholeheartedly.”


Mady H.

“Had a meet and greet afternoon for Skipper and Mady was so great! Mady communicated during the stay and Skipper did well with her dog and kitty. We will be using Mady again for sure <3”


Laura R.
“Laura is wonderful! She is very responsible and dependable. She has great experience with dogs, from obedience and agility training with her own dog, to extended caregiving for others' dogs. She would be a loving friend to any dog in her care.”


Violeta E.
About: I am dog mom of two; I have two golden retrievers and have experience working with puppies and also adapting their training skills and making sure they are stimulated. A stimulated dog, is a happy dog. I also have experience making healthy homemade cooked meals, as I feed my dogs daily a healthy home cooked diet. I currently work from work Monday- Friday but have a flexible schedule and also available for weekend work. I currently am looking for side work to maintain a busy schedule and lifestyle. I have two golden retrievers at home, Brooklyn and Belle. I will always ensure safety if a pet is brought to my home and make sure a crate is available at all times in case a pet needs space. If I travel to your home, please assure I will take all measures to make your pet comfortable and build my trust with every visit.


Robin K.
“Hi Robin K would be an awesome sitter or dog walker. I know she has a love of animals & a great sense of responsibility for caregiving. I would hire her in a minute.”


Giannina S.

“Giannina and her family are very nice people. They watched my dog for a day while I was at work. He came home content and tired out.”


Laura T.
“Laura was very welcoming and I felt confident leaving my anxious dog with her. Her property is a beautiful place for animals to spend the day. We had a nice conversation at pick up and I appreciate her kindness. My dog was very comfortable with her.”


Cailley C.
About: I work at home and have time to make sure all of your pets needs are met. I am comfortable with dog and pets of all different temperaments--- I've taken classes on canine behavior in undergrad and have a good understanding of dogs with unique needs. I have a lot of experience with cats and dogs of all ages and personalities. I have two cats who get along well with dogs. My sister and I live in a stand alone home with a large yard for animals to play in, and a lot of space in the home. Our home abuts conservation land with lots of trails for walking and playing. I would be honored to care for your animal companions, and can ensure they will be safe and happy during their time with me :) I work from home and have alot of flexibility with my job so I can ensure your animal companion will have my full attention throughout the day, including walks, and hikes if desired! Happy to board pets, large home and yard with two friendly cats. Can take your dog on walks throughout the day leashed or unleashed (depending on need). Experience with geriatric dogs and puppies alike !


Jillian H.
“I can’t say enough good things about Jillian. She went above and beyond in the care she took of our home and pets. Everything was in tip top shape when we returned and it was clear the pets had received ample attention. I would highly recommend her to anyone looking for a sitter, but I also wish she was kept a secret so she could be available for us all the time!”
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1. Search
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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
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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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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 Aug 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 Aug 2025, 64 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 offering doggy day care with repeat customers have an average of 3 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 64 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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.
