Dog Walking in Winchester

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

1. Nikki

Dog's Bestfriend!

Medford , MA, 02155

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

3 repeat clients

"Nikki was enthusiastic. Was on time and took Charlie for a good solid walk. I would absolutely have Nikki walk my dog again. Ask good questions about her and... (more)"

2. Sophie

I spoil your dog like my own!

Reading , MA, 01867

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

45 repeat clients

"Sophie is amazing! We just started with Sophie recently, and we are planning to use her long term for my dog Hunter. Hunter seems to love her so far, and i... (more)"

3. Joselyn

I'll ♡ your animal(s) like my own

Somerville, MA, 02143

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Joselyn is great with our dog. She is very warm and understanding. She is happy to accommodate our routine and requests. She is very communicative, asking an... (more)"

4. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

17 repeat clients

"Nicole did an excellent job with Charlie. Sent videos, and a picture. She met Charlie the day before, and she was able to step in on short notice. A huge hel... (more)"

5. Andrew

Compassionate Animal Lover!

Reading, MA, 01867

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Andrew is a kind, gentle and responsible person. His love of all living things is evident in his dealings with animals and their humans. He loved taking my d... (more)"

6. Jessica

I'm trustworthy and passionate

Malden, MA, 02148

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jessica is the most kind and loving pet-sitter! She took amazing care of our dogs, Moose and Gronk, and I felt reassured that not only were their needs met,... (more)"

7. Cheryl

Lets Doggie Party!

Burlington, MA, 01803

Dog Boarding, Doggy Day Care, Dog Walking

26 repeat clients

"Cheryl worked for me at Home Buddies, Boston NW. She was a very loyal, dependable animal lover and a great worker. She cares about her job and has a great w... (more)"

8. Kailey

Life is ruff! I can make it easier

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Max and I are so lucky to have Kailey! She is kind, dependable and very knowledgeable. Max is looking forward to his next walk with her! (more)"

9. Gretchen

Woof, Woof, Woof!

North Cambridge, Cambridge, MA, 02140

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Gretchen was wonderful and really flexible! Maggie really enjoyed her walk and I appreciated the detailed description of the walk and Maggie she gave! I wou... (more)"

10. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

" Sara is a lovely person and she really loves a care about nature and animals, She was born in Hawaii with a lot of contact with animals and nature I believe... (more)"

11. Andrea

Loving Pre-Vet Student

Medford, MA, 02155

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

7 repeat clients

"Andrea is very friendly and comfort with Simon. Simon after only 3 visits is excited to see Andrea and go for a walk. (more)"

12. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Grace was great with our pug. He doesn't always like new people coming in, but was very comfortable with Grace. She sent updates each time she took him out... (more)"

13. Sarah

Empathic and flexible dog lover

Somerville , MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Sarah took excellent care of my schnauzer, Turbo. Beyond dogsitting for me, she and I also work together at the same hospital. She is a calm, warm, and respo... (more)"

14. Alisha

Dog Groomer, Puppy Foster Parent

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

"Alisha's love for her dog, as well as any living creature, is evident through her willingness to dog-sit my high energy, 10-month old lab! She and her boyfri... (more)"

15. Shannon

Nursing Student/Dog Lover :)

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Shannon is a dog lover. She's watched and cared for my dogs several times and always does a great job. I have 2 chihuahuas that take a while to warm up to pe... (more)"

16. McKenzie

For the love of dogs

Melrose, MA, 02176

Drop-In Visits, Dog Walking

"McKenzie is amazing- she kept me updated and was super timely! Shelby wanted to be her bestfriend from the very first second she met her! She looks forward t... (more)"

17. Cameron

A life without dogs is not a life

Arlington, MA, 02476

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Cam is a total dog lover and has 3 wonderful dogs. He is very responsible and trustworthy, and takes great care of his dogs and also his rabbit. (more)"

18. Naomi

Flexible dog walking and sitting!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

About: Thank you for checking out my profile! I frequently care for my family's medium sized dog (a cockapoo named Tuesley) on weekends, and I love the co... (more)

19. Luciana

Join the pack

Medford , MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Luciana has known my dog, Elsa, since she was a puppy. Luciana's dog Xiina and Elsa often have play dates. Luciana seems to have a special connection with t... (more)"

20. Megan

Must Love Dogs

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Meg was a great sitter for my little yorkie, Seamus! I could tell she loves dogs and knew exactly how to make them happy and well cared for. She was easy to ... (more)"

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Dog owners love Winchester dog walkers on Rover. 28 owners have reviewed walkers in Winchester, MA, giving them an average rating of 4.9/5.

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

We've been there: rushing home during every lunch break to take the dog for a quick walk around the block. Good news: You can easily find and book dog walking services on Rover. Whether you need a one-time dog walker or someone to take your dog for a stroll every day, we've got you covered. Exercise for your dog and peace of mind for you are just a few clicks away. Every walk is covered by premium pet insurance, at no extra cost to you. You can even ask your dog walker to send you a photo update. Whether you already have a favorite pet sitter on Rover or you're new to the site, we'd love to connect you with a dog walker near you the next time you're unavailable. We're confident you and your dog will love it.

Wondering what you should be paying for a walk? Check out our standard dog walking rates for a comparison.