Dog Walking in Winchester

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

1. Jenna

I'll bring the lint roller!

Burlington, MA, 01803

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

About: Hello, my name is Jenna! I am an overall animal lover, though dogs have always been my favorite animal due to their unconditional love and high ene... (more)

2. Alysha

I'll run with your dog.

Belmont, MA, 02478

House Sitting, Dog Walking

2 repeat clients

"Alysha has a very kind and loving heart for animals. She has an excellent work ethic, always timely and hard-working. The thing I like most about Alysha is t... (more)"

3. Candice

Love to teach old dogs new tricks

Somerville, MA, 02144

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

2 repeat clients

"Candice was great! She walked our dear pug this week, and we will definitely be rebooking while we need extra help over the summer. Candice was attentive, ga... (more)"

4. Kiera

I'm an experienced dog lover!

Everett, MA, 02149

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I have owned dogs for my entire life, and I've studied them since I was young. I have worked for dog daycare facilities, and I have volunteered wit... (more)

5. Nikki

Dog's Bestfriend!

Medford , MA, 02155

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

4 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)"

6. Sophia

Loving, Responsible Dog Sitter

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Sophia did an outstanding job with our pup! She communicated with us throughout her time with our dog while we were away. After the walk Sophia even spent a ... (more)"

7. Kayla

Dog Lover/Caretaker

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

"For years now, Kayla is and has always been my first choice to care for my much loved, 12 pound and 4 year old Havanese dog, Phoebe, when I'm away from home ... (more)"

8. Maxwell

Excited to meet new dogs in my area

Medford, MA, 02155

Drop-In Visits, Dog Walking

"My dog OG loved walking with Max! (more)"

9. Cameron

A life without dogs is not a life

Arlington, MA, 02476

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

2 repeat clients

"Cam loves dogs more than anyone else I know. He grew up with three of them, so he's very attuned to what dogs need and how they communicate. He goes above an... (more)"

10. Natasha

While you're away your pet can play

Woburn, MA, 01801

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

"I'm very glad to have Natasha walking my dog, she was very kind to come to my house on a last min call to meet me and my dog before she start working for u... (more)"

11. Kailey

Life is ruff! I can make it easier

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Dogs really liked Kailey. She is nice young lady who was great with my puppies! (more)"

12. Sarah

Empathic and flexible dog lover

Somerville , MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

13. Julie

Belly rubs & puppy massages

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"I have known Julie Orsillo for over a year and cannot say enough positive things about her. Julie is amazing not only will she love your dog when walking or... (more)"

14. 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)"

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. Margaret

Dog-loving grad student w/ backyard

Somerville, MA, 02144

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

About: Ever since my first pet dog at age eleven, I have been hooked on dogs. I have worked with rescue organizations and have pet-sat for my friends and ... (more)

17. Christine

Home full time. Vet Tech experience

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Chris has been looking after all my pets over the course of 2 decades. She is completely trustworthy and she is a huge animal lover. Plus, she is a certified... (more)"

18. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Sara did an outstanding job with Charlie. She was able to walk her on extremely short notice. Dog was happy and in good spirits when we got home. She took ca... (more)"

19. Cheryl

Lets Doggie Party!

Burlington, MA, 01803

Dog Boarding, Doggy Day Care, Dog Walking

27 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)"

20. Kira

Ready to play!

Lexington, MA, 02420

Drop-In Visits, Dog Walking

About: When I turned nine, my parents gave me the best birthday present in the world: a brother... and by brother I mean dog. But I love him like a brothe... (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.