Dog Walking in Winchester

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

1. Brendan

Very experienced and responsible!

Melrose, MA, 02176

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

1 repeat client

"I don't even know where to start! The amount of love, care and attention Brendan gave to my puppy is unparalleled. Brendan went out of his way to accommodate... (more)"

2. Gabi

Must Love Dogs

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Gabi is one of my most responsible companions if not the most responsible one. Her responsibility has always been demonstrated through school work and being ... (more)"

3. Mary

Pawsitively the biggest dog lover!

Somerville, MA, 02145

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Mary is great. Our pupper has a blast with her and she is able to handle his fairly boundless energy. She is very good at providing updates, extremely respon... (more)"

Confirmed President's Day Availability
4. Genta

Home full time - A Fuzzy Vacation

Malden, MA, 02148

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

21 repeat clients

"Genta does a great job with my large, anxious dog. He adores her and she's been very easy to work with- a good communicator and very reliable. (more)"

Available this weekend
5. Sereena

Guaranteed to love your dog

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"I have been best friends with Sereena since we were kids, so I can attest to her forever long love of dogs. But my most memorable moment with her and my dog,... (more)"

6. Becky

Available all day Monday,Tuesdays!

stoneham, MA, 02180

Drop-In Visits, Dog Walking

"Becky brings her therapist mentality into her love for all animals. Becky has always been an animal lover especially dogs. When she shows you baby pictures o... (more)"

7. Alexandra

Huge park outside my front door

Winchester, MA, 01890

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

1 repeat client

"Alexandra is a nurturing and responsible animal lover. She understands that each animal needs a different level of devotion and care. I completely trust her ... (more)"

8. Joe

“Marley and Me” made me cry

MEDFORD, MA, 02155

Drop-In Visits, Dog Walking

"Joe is fantastic with dogs! My dog absolutely loves him since he takes her for walks and gives the best butt scratches! Your dog is guaranteed to well cared ... (more)"

9. Casey

Will Take Your Dog to the Fells!

Malden, MA, 02148

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

"Casey is an avid dog lover and enjoys being in their company. I own two senior mini schnauzers (ranging from 16-19 lbs) that require at times, significant a... (more)"

10. Alanah

I love dogs

Woburn, MA, 01801

Dog Boarding, Drop-In Visits, Dog Walking

"Alanah is a loving, reliable, responsible, and damn right awesome person to take care your pup! I'd trust her with my dog any day of the week. My pup jumps w... (more)"

Confirmed President's Day Availability
11. Brigid

Passionate about pets!

Medford, MA, 02155

Drop-In Visits, Dog Walking

About: Hi there, I'm Brigid! I'm currently in my second year of grad school at MassArt studying fashion design. Ultimately, I want to work in the industry... (more)

Available this weekend
12. Erica

Teach online lots of time for pets

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Erica is a wonderful house sitter, who took care of our whole house, plus our two aged cats for over two weeks. The cats require a lot more care than younger... (more)"

13. Danielle

Home Full-Time, Dog Lover

Stoneham, MA, 02180

Dog Boarding, Drop-In Visits, Dog Walking

"I have had the pleasure of living with Danielle and her dogs (and occasionally cats) off and on over the last 10 years. She is a loving and enthusiastic pet... (more)"

14. Annsleigh

I'll take your dog for long walks!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

About: I'm a true animal lover with open availability on the weekends and some weeknights. I'm responsive, reliable, and responsible. I have many years of... (more)

15. Kat

Fitness with Fluffy!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

About: I recently moved to Boston and away from my parents and their older dachshund Maxx. I miss Maxx and would love to play with a dog again! I work fro... (more)

Confirmed President's Day Availability
16. Maria

Wagging Tails & Peace of Mind

Stoneham, MA, 02180

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

8 repeat clients

"Maria's love for all animals is what I think makes her a perfect pet caregiver. She has been caring for my pets (and home), for several years. I travel with ... (more)"

17. Sarah

The Puppy Playhouse

Medford, MA, 02155

Dog Boarding, Doggy Day Care, Dog Walking

36 repeat clients

"Sarah has been wonderful with our dog Stan this week! She has helped us both with daycare and walking. Sarah's home is a warm and welcoming place to leave ou... (more)"

18. Hannah

Care and fun hikes for your dog!

Stoneham, MA, 02180

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

About: I’m a musician,violin teacher, pet sitter and dog walker. I love and respect all animals. I grew up with pets my whole life, at some point I had 8 ... (more)

Confirmed President's Day Availability
19. Gregory

Lifelong Dog Owner & Lover

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Mr. Gregory was an excellent dog sitter when he watched over my doberman last year. I can truly vouch for his enthusiasm and compassion for dogs as I know he... (more)"

Confirmed President's Day Availability
20. Emily

Gingerplum Home Away Pet Services

Stoneham, MA, 02180

Drop-In Visits, Dog Walking

"Emily is a fantastic dog walker! She has been the only walker Henry has had and has always taken the best care of him. She is extremely reliable and responsi... (more)"


Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money as a dog walker in Winchester, MA. If you're not sure where to start, visit our page about how to become a dog walker. We're always happy to include new dog walkers in our dog walking service listings, and the simple review process means you can start your own dog walking business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog walkers have access to premium pet insurance, a third-party background check, and cashless payment feature, so you don't have to worry. Join our pack today!

When you book dog walking services on Rover, you'll be able to connect with a dog walker who's a good fit for you, your dog, and your lifestyle. Your walker can provide dog walking updates with start and stop times, a map of their walk with total distance, info about pee, poo, food and water breaks, and photos of your dog in action. Every walk booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee.

Looking for a quick solution to your dog walking needs when you're short on time? Then you'll love the Rover dog walking app. The Rover app features hundreds of highly rated, trusted dog walkers, and you can scroll through the options or simply rebook your regular dog walker in seconds. Your dog walker can share real-time photo updates via the Rover dog walking app, and with the app's cashless payment feature you'll be able to compensate your dog walker quickly and safely - no need for cash, checks or tips.

Speaking of payment, the cost of dog walking in Winchester, MA may surprise you - in a good way. That's because there's a dog walker on Rover for nearly every price range and lifestyle. Curious about how much you can expect to pay for dog walking on Rover? Check out our average dog walking rates to get an idea before you start a conversation with an individual dog walker.

When you need dog walking services in Winchester, MA, you'll be amazed at how easy it is to find the ideal dog walker with Rover.com. We take the guesswork out of selecting the perfect Winchester dog walking services for your needs. The dog walkers listed on Rover have been reviewed and approved, and - most importantly - they love dogs. In fact, 95% of reviewed stays and walks have a perfect five-star rating. When a dog walker in Winchester, MA joins our site, they complete a background check. You'll be able to see that they've passed the background check when you view their individual dog walker profile. No matter what level of support you're looking for, you're sure to find a great fit for all your dog walking needs in Winchester, MA with Rover's dog walking services, whether it's a one-time emergency or a daily appointment.

In short, when you use Rover to find a dog walker in Winchester, you can rest easy knowing that your dog is having a great time.