Doggy Day Care in Winchendon
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 Winchendon doggy day care sitters
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

“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.”

About: I have had indoor cats for the past 24 years. I have pet sat for dogs and cats personally. I have house sat twice for a dachshund and doberman. These were contacts from my mom’s pet sitting job years ago. I had a beta fish for about 3 years. I can walk and play with the dogs and cats, feed them, etc. I will provide what is going on and what is being done, sharing pictures and videos as much is wanted. I currently work full time Monday through Friday. I can work from anywhere. I am available evenings during the week and available on the weekend. This is a side hustle and to offer some help for anyone that need it. We have a dog and a cat. We aren’t sure how our dog and cat would be to other pets in our home. I am happy to come to yours. Whatever is needed.
“Thank you so much for all of the wonderful pictures and the videos of Miss Tulips day with you. I hope she was a good girl for you but thank you so much for the exceptional care and love you gave her. We will most definitely have you watched her again for us. Thank you ☺️”

About: I've been around animals my whole life and currently have two pet goats who we spoil like dogs. We have 30 acres of beautiful land surrounded by woods, which is a perfect haven for running, fetch, and all sorts of outdoor shenanigans. I work remotely from home with a flexible schedule. I typically work a few hours in the morning, and then am outside working on projects and playing with the animals all day. We have a large property (about 30 acres) surrounded by woods with lots of room for your dog to run and explore. We also live near some great hiking trails.
About: I love animals and have been around them as long as I can remember. I have extensive experience with dogs and cats, from birth to their last breath. I believe in positive reinforcement training. I am very loving and treat all animals with respect but can be strict when required for safety. With me your babies will feel like they are at home away from home. I work from home and have a very flexible schedule. I am available almost always and your fur babies will have lots of love and company. I have a large grassy yard, and I live near a pond and multiple trails. I also have a Chihuahua mix girl, who is very friendly and loves making new friends.
“Maggie is awesome!!! Kallie had a great day with her. Took her out to the doggy park and tired her out!! Def my go to next time I need a pet sitter for the day! Thank you so much!!!”

About: Hi all! I am a stay at home mommy of two adorable and sweet teens . We are a family of animal lovers. I am a pet owner through all my life. I currently have 5 cats.. and one gentle husky/Collie sweetest Puppy ever who craves for companionship <3 I have a nice area for my cats (also a nice fenced cat patio) and a decent size back yard. I live on quiet dead end st. If your dog is boarding with us. At night time, He will have three options. Have its own crate, Or it can be free (as long as it is house trained and won't chase after my other fur-babies -cats- ??) Orrr Sleep in my bed with all my other fur-babies. If you need me to come to your house. I could also do that as well and provide kisses, hugs, playtime, food, water and cleaning. (Special instructions welcome) Oh and please I could also take care of and board Cats or other pets too!!! I love them all and it’s going to be my pleasure! ( I do have a separate area for all my cats and it’s full of fun stuff and catnip ??. But they do have full access of the house at all time) No outdoor cats please. Please come visit me and my fur babies! I am a stay at home mom. And I have plenty of free time in my hands. It would be a pleasure for me and my teens to take care of your pet. It will depend on the client's preference. I could do crating, or free run of the house. (If pet is house trained). Nice decent yard and safe neighborhood.
“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!!”

“Giannina came through at the last minute to watch my dog for the day. I prefer when sitters send photos and videos because it helps me feel reassured that he is content. She is busy with her children so I didn’t receive any. Anyway, I’m happy he was taken care of.”

About: I'll care for your dogs like no other. Whatever your pet needs to be happy, they will get. Walks? Treats? Hugs? Massage? Toys? You name it. Just love dogs and want to give back to the many dogs I have owned and cared for in my life. Have years of experience with pet sitting. I work from home and have plenty of time to care for your pet. I am also available on weekends. Can accommodate many varied schedules. I have a fenced in yard and have over 2200 square feet of home. I have access to many trails for walking, hiking, and swimming. Star, my friendly and loving black lab lives with me and will provide the perfect setting for your dog.
“Jenna was great with my pup Lily! She’s watched her twice now and the second time Lily ran straight to her door and strolled right in when I dropped her off. I know my girl is totally safe and happy with Jenna, highly recommend :)”

“This week I was extremely impressed with the kindness of Michael as he offered to watch Charolette in New Year’s Day. I have an early schedule so drop off was 6:30 am so this was exceptional commitment to customer service I’m my regards. I also have a scheduled that fluctuates and last week was put on call one of the days that I pre paid canceling a day I’d need service last minute. Michael offered to watch Charolette overnight no charge New Year’s Day as I was scheduled to work two 12 hr shifts back to back as a convenience to me. I am so appreciative and happy with the care I’m receiving using Michael’s business for the care of my dog whom I consider family. Thank you Michael for all you do!”


“Tracy was such a good sitter for our dog! She had great communication and was very friendly and accommodating to our schedule. She provided plenty of photos and updates as well. We’ll definitely book her again if we need a sitter!”

About: I have 14+ years experience in the veterinary field. Learning about animal behaviors, preventative care and physical health is a passion of mine. I am a very well rounded animal enthusiast that loves to stay busy. Some of my extracurriculars include training my Australian shepherd, whether it’s dock diving, agility or overall obedience. I will hold each pet to standards that support good manners, so some training may be associated with my services. I strive to exercise your fur babies intellectually as well as physically. I am very detailed oriented, and consider myself very observant. I’m not afraid to communicate and ask questions regarding your pets’ needs. I would be caring for your pet around my typical work schedule, which is M-F ~8-6pm, but I can always drop in mid day during lunch. Communicating your expectations so I may practice proper time management is important for a successful and stress free pet sitting job. I have a very well socialized 5yo male, 50lb, Australian shepherd, Oshie and he loves to play. Additionally I can provide walks, and play sessions. Hikes are also supported.
About: Hello, my name is Amy, I am 36 years old, a huge animal lover with lots of pet experience! I’m currently in Troy NH so I’m open to anyone in need in the surrounding towns or a bit further. I’m available to do either daycare or boarding in my home 7 days a week. If you have any questions or anything please feel free to message me anytime, and I’d be happy to speak with you! I have a flexible schedule and I’m looking to make this a regular job. Hope to hear from you all soon and thanks for taking the time to read this! Have a wonderful day, and I’ll talk to you soon. Click here for $20 off your first booking with me :) https://www.rover.com/sit/amyp86790 I have a completely open flexible schedule 7 days a week and should be able to meet all your needs! I’m available morning and night just shoot me a message I care for pets in my home. I will walk and play with them, bathe them, feed them and snuggle them, whatever they need :)
About: Having grown up around a diverse set of animals then adopting 2 dogs of my own in adulthood, I bring a thorough, well rounded background in pet care. I am single dad (kids live here part-time) who currently works a corporate 9-5 job full-time from my home office in Leominster, so I have a lot of flexibility during the work days during the week, and then my weekends are very open too around kids activities. I live in a pet-friendly apartment complex within a wooded area with land so this gives a good environment for comfortable interior space as well as walking pets outside.
About: I've taken care of dogs for as long as I can remember. I've always been a very empathetic person and just love to wave and say hi to dogs going by. I've had dogs of all sizes. My most recent is experience with Chihuahuas. I just love them! I've raised 2 dogs from 8 weeks old. I love all stages of a dogs life, from puppy to senior. I also have experience with senior dogs who need special care and medication. I'm currently working for myself, so I have plenty of time to spend playing, caring, loving and walking with your pets. I'm available M-F 9-6 pm. I like to make sure the pet is comfortable. I want the pet to feel at home with me. The least amount of change from the pets daily activities are important for the pet to feel safe and happy.
“Jarica has been prompt, friendly, professional and flexible in all our communications and bookings. Our pup Cider loves her!! She is so excited to see Jarica every time we drop her off. Jarica has a beautiful, open yard, away from roads where dogs can run around. She is very attentive and clearly loves to care for dogs! We highly recommend booking with Jarica!”

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.
Over 15 pet parents in Winchendon have booked doggy day care
Winchendon dog parents share their Rover experiences
Amanda was very kind and patient with our nervous dog. She took time to sit with us during a meet and greet, playing and chatting until our pup warmed up. On her first day of daycare, I appreciated Amanda's check ins and photos to let me know how it was going. It was clear our dog had a lot of attention and love throughout her day from Amanda and her family. Thank you!

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The median cost per day for doggy day care in Winchendon is $40
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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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Sitters in Winchendon average 4 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 Winchendon 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, 92 sitters provided doggy day care in Winchendon. 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, 85% of Winchendon sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchendon have an average of 17 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 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 Winchendon.
Winchendon 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 Winchendon 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 92 sitters offering doggy day care in Winchendon on Rover, so you’re sure to find the perfect match for your dog! In Winchendon, 93% of sitters offer daily exercise, 93% offer medication administration, and 93% 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.

