1. Haichi

Dog Lover Who Works From Home!

Brookline, MA, 02446

Dog Boarding, Doggy Day Care

10 repeat clients

"SO glad I found Haichi! I had a last minute key situation and needed to find someone for the next day who could bring my dog into their home while I was at w... (more)"

2. Kelly

Safe and Fun for your furry one!

Melrose, MA, 02176

Dog Boarding, Doggy Day Care

6 repeat clients

"Kelly was a trustworthy and very kind sitter for Lucy ..after Lucy Had a tumor removed off her back I was nervous to leave her home alone. Kelly sat with her... (more)"

3. NIL

Dog Paradise With A Dog Lover !

Central, BOSTON, MA, 02114

Dog Boarding, Doggy Day Care

29 repeat clients

"Niy is awesome! Communicative, friendly, and responsible. Her love of dogs is obvious and genuine. Louie was happy to see her every morning. Highly recommend. (more)"

4. Caren

My kids love dogs!

Malden, MA, 02148

Dog Boarding, Doggy Day Care, Dog Walking

3 repeat clients

"My boyfriend and I have had our girl for just shy of 2 months and we are both first time puppy owners. I recently had to be out of town for a few days and m... (more)"

5. Cheryl

Lets Doggie Party!

Burlington, MA, 01803

Dog Boarding, Doggy Day Care

16 repeat clients

"Max came home very tired today. Her fenced back yard is the best! Max could come in and out through the dog gate. Cheryl sent me pictures throughout the day ... (more)"

6. Nicole

A Dog Lover & Rescuer Who Is Fun

Burlington, MA, 01803

Dog Boarding, House Sitting, Doggy Day Care

5 repeat clients

"Nicole was great! She was patient with my worried mom routine, and clearly attentive to my 10 month old pup! She made sure her dog got along with mine and ... (more)"

7. Walter

A Dog's Place is in the Home

North Cambridge, Cambridge, MA, 02140

Dog Boarding, Doggy Day Care

28 repeat clients

"Bella seemed to be content at Walter's house. She especially likes Walter's pup, Vinnie. Walter's house is calm and clean and provides a nice environment f... (more)"

8. Cam

We are dog lovers who work at home

Reading, MA, 01867

Dog Boarding, Doggy Day Care

1 repeat client

"Super friendly people that took great care of my dog Zsa Zsa. I got photos of her playing in the yard and relaxing inside throughout the day. I will definite... (more)"

9. Ian

Lookin' to chill w/ your doggo!

Allston-Brighton, Allston, MA, 02134

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Dear Dog-Loving Friends, I'm pleased to recommend Ian as a wonderful pet pal. I've known Ian for many years, and during that time he has provided care ... (more)"

10. Kinga

Goofball who wants to pet dogs

Allston-Brighton, Allston, MA, 02134

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Kinga was kind, understanding, and very caring towards Bear. Her diligence and investment in his well-being was apparent. She is reliable and responsible a... (more)"

11. MacKenzie

I am a young and energetic person.

Melrose , MA, 02176

Dog Boarding, Doggy Day Care

1 repeat client

"MacKenzie took good care of our dog in her home. She has 2 other dogs who got along great with our dog. When we got home our pooch was tired and happy! Pl... (more)"

12. Christine

Future Vet Seeks Lonely Furbabies!

Burlington, MA, 01803

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Guinness had a great time with Christine and her family. She treated him like her which I really appreciated. I also loved that she is going to school to be ... (more)"

13. Julie

Cuddles, playtime, fun and naps

Woburn, MA, 01801

Dog Boarding, Doggy Day Care

2 repeat clients

"Julie takes care of our baby Boston Terrier while we are at work during the week. I have no worries leaving him there because I know he is very well cared fo... (more)"

14. Brianna

The dog nanny

Malden, MA, 02148

Dog Boarding, Doggy Day Care

"I can definitely can vouch for Bri! She is extremely responsible and very trust worthy. She is such an animal lover! She has a way with dogs that's for sure (more)"

Available this weekend
15. Jarrett

Flexible Freelancer for Fur Friends

Somerville, MA, 02145

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Jarrett has been a close friend of mine for 15+ years, so I can say with certainty that you would be hard-pressed to find someone more kind, responsible, and... (more)"

16. Joann

Loving caring patient and generous

Medford , MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: You can ask my best friend how Well I took care of her dog. She was a beagle with some health issues , we all loved her and she loved us. Unfortun... (more)

17. Sophie

It's a Ruff Life!

Reading , MA, 01867

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

32 repeat clients

About: Hi! I previously worked as a veterinary technician for over 2 years, and I have several years of experience with dog walking and pet sitting. I'm c... (more)

18. Benjamin

Your dogs vacation home

Arlington, MA, 02474

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

20 repeat clients

"Being new to the area, I was hesitant to leave my 1-year-old 90 pound puppy with a stranger, but after talking to Ben at the meet and greet, I was confident ... (more)"

19. Bryna

Kind, Caring, Loves Walks

Malden, MA, 02148

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Bryna adores dogs and they respond immediately to her passion. She's lived with and cared for dogs most of her life, and provides exceptional and skilled ca... (more)"

20. Nicole

Can't imagine a life without dogs!

Winchester, MA, 01890

Drop-In Visits, Doggy Day Care, Dog Walking

About: I work from home and spend my day cuddling up with my dog while I work. I have taken in family member dogs and neighbors' dogs to add more snuggles... (more)

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Learn About Premier

Dog owners love Winchester sitters listing doggy day care on Rover. 28 owners have reviewed dog sitters in Winchester, MA, giving them an average rating of 4.9/5.

Want to be added to this list of sitters in Winchester? Become a pet sitter or dog walker on Rover.

We've been there, cancelling meetings or plans with friends to make sure you can be there for your dog. Good news: You can easily find and book doggy day care on Rover. Whether you need a one-time daytime pet sitter or someone to take care of your beloved pet every weekday, we've got you covered. Care for your dog and peace of mind for you are just a few clicks away. And, just like with overnight stays, dog day care booked through Rover is covered by premium pet insurance, and our sitters have access to 24/7 support. If you already have a favorite overnight sitter, ask them if they offer day care too. Or, if you've never used Rover, this is the perfect opportunity to find a new best friend for your dog when you're at work. We can help you find a sitter who'd love to watch your dog.