Dog Walking in Winchester

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

Confirmed availability
President's Day
1. Sally Ann H Verified Enhanced Background Check

I'm honored to care for your bestie

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Sally Ann was just awesome with my very shy small dog. I knew when she was there to walk her. She sent pictures and a description of how the walk went. I wou... (more)"

2. Kelly Verified Enhanced Background Check

SAHM who LOVES doggies & kitties

Arlington, MA, 02476

Drop-In Visits, Dog Walking

"Kelly was fantastic! We booked her for two dog walks this week and she went above and beyond in terms of walking, communication, and love given to our dog! W... (more)"

3. Kevin Verified Background Check

They call me "The Pug Whisperer"

Somervill, MA, 02144

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

"Kevin is great with my dog. He was able to take her out for potty and to the dog park to make some new friends! He even sent a photo of her playing. Will def... (more)"

Confirmed availability
President's Day
4. Alan Verified Background CheckRover 101

Keeping your dog happy and fit

Arlington, MA, 02476

Drop-In Visits, Dog Walking

"Alan did a great job walking Domino. He really loves dogs, and was reliable about showing up to take her out and communicate with me afterwards. (more)"

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5. Natasha Verified Background Check

Rkain or shine, I'll walk your dog.

Arlington, MA, 02476

Drop-In Visits, Dog Walking

"Natasha is just fantastic Very high energy, engaged individual. She is handling very well my high energy Australian Shepherd Love her communication and fl... (more)"

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6. Suriah Verified Background CheckRover 101

Dedicated and Loving Animal Care

Medford, MA, 02155

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

"Suriah has been great with Teddy! (more)"

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7. Debra Verified Background Check

I am home full time. Fenced yard

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"Debra is the best! Always takes such good care of my dog:) (more)"

Confirmed availability
President's Day
8. Kate Verified Background CheckRover 101

Home Full -Time Large Fenced Yard

Woburn, MA, 01801

Drop-In Visits, Dog Walking

"Kate is very reliable! She’s walked my Kasey a few times now and always does a great job taking care of her. (more)"

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9. Jessica and Dave Verified Background Check

Dog Walks and Kitty Care Arlington

Arlington, MA, 02476

Drop-In Visits, Dog Walking

"Jessica takes such good care of my dog who has anxiety and is blind. She really goes to great lengths to make sure she feels comfortable and safe and we are ... (more)"

10. Cory Verified Background Check

Love of animals of all kinds!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Cory is great! We've booked him a few times to walk our two rescue dogs, who are nervous around new people, and he is super patient with them. They love ha... (more)"

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11. Sonya Verified Background Check

Experienced pet sitter/dog walker

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"Sonya is compassionate, kind, and very reliable. She is a life long animal lover and it definitely shows when she is interacting with animals! She has a way ... (more)"

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12. Ana Verified Background Check

love, care and play for all pets ❤️

Winchester, MA, 01890

Drop-In Visits, Dog Walking

"Ana has been a super reliable and responsive walker for our dog! She's always there on time and gives great updates for us. I'd definitely recommend her as a... (more)"

13. Kimm & Kenn Verified Background Check

Love dogs, love to walk!

Woburn, MA, 01801

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

"Kenn is always on time and Tuck loves walking with him. He comes home tired and ready for a nap! (more)"

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14. Meg Verified Background Check

Love to take your dog on a hike !

Winchester, MA, 01890

Drop-In Visits, Doggy Day Care, Dog Walking

"Meg was great! She took Dany on long walks around our neighborhood and even further some days. She loves dogs and very reliable. I would highly recommend usi... (more)"

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15. Bridget Verified Enhanced Background Check

Dog loving grad student

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Bridget took care of my dog for years. I could count on Bridget to do what I asked and when I asked - take my dog out, walk, feed and water and play with the... (more)"

16. Amelia Verified Background Check

Let's play fetch in my backyard!

Medford, MA, 02155

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

"Amelia loves all animals and takes really good care of them. She is dependable and communicates well. She sent me cute pictures of my dog and even taught he... (more)"

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17. Eric Verified Enhanced Background Check

I’m home all day so walks away!

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"Eric is fantastic! He is reliable, patient, always extremely punctual, and really wonderful with our Harper! He always sends photos, fills out the rover card... (more)"

Confirmed availability
President's Day
18. Oana & Oliver Verified Background CheckRover 101

For the love of dogs

Woburn, MA, 01801

Dog Boarding, Doggy Day Care, Dog Walking

"I've known Oana for many years and admired her love for animals of all kinds and her advocacy for animal rights. Through her upbringing as part of a family o... (more)"

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19. Sandy Verified Background Check

Pet LOVER! Can’t wait to meet

Arlington, MA, 02747

Drop-In Visits, Doggy Day Care, Dog Walking

About: Ive had Pets of my own. At this moment I have two of my own a Shit-su (9 yrs old) and a chihuahua mix (1 yr old). I love to walk, play with them. ... (more)

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20. Elizabeth Verified Background Check

Can’t wait to meet your animal!

Stoneham, MA, 02180

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

"There's nothing better than someone who loves your dog the way you do! Elizabeth is that person. You can see the joy she has for animals, dogs in particula... (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.