Dog Walking in Winchester

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

1. Steve

Playmate for pups!

Somerville, MA, 02145

Drop-In Visits, Dog Walking

4 repeat clients

"Steve was incredible with Jed. He was quick to respond to my inquiry; super thorough at our meet and greet; very communicative leading up to, and throughout,... (more)"

2. Evelyn

Ready for energy-packed play & naps

Arlington, MA, 02476

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

"Evelyn is an extraordinarily responsible and caring dog walker. She has a deep love of dogs and has cared for all kinds—healthy and active, elderly and ill, ... (more)"

3. Ang

Providing extra treats and snuggles

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

"Angela is an amazing dog sitter. It is obvious that she loves animals. My dogs are always excited to see her and she is so patient with them. (more)"

4. Sierra

Punctual Walker 4 Rambunctious Dogs

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

About: Hey there! I just moved to Boston after graduating from Middlebury College (Environmental Policy!) and have years of experience caring for domestic... (more)

5. Alex

Your dog will feel at home

Medford, MA, 02155

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

About: I work from home, so I can make sure your dog is never alone. I foster dogs for a non-profit organization; I only take one dog a the time from the ... (more)

Available this weekend
6. Anna

Love to run and play with dogs!

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Anna has walked, feed and cared for Sophia my 77lb old English stubborn 3yr old bulldog. She’s responsible & reliable. Sophia is very happy when she comes... (more)"

7. Drew

I'm there for your dog when needed

Malden, MA, 02148

House Sitting, Drop-In Visits, Dog Walking

"Drew did a great job! He was timely and great with Gracie. He was covering for our regular dog walker for part of this week, but would definitely inquire wit... (more)"

Confirmed Memorial day Availability
8. Alan

Keeping your dog happy and fit

Arlington, MA, 02476

Drop-In Visits, Dog Walking

3 repeat clients

"Alan is great with my dog Maisy! Kind Gentle and Thoughtful he has always kept me well informed. I would reccomend Alan! (more)"

9. 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)"

10. Emmy

the charlie brown to your snoopy

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Emmy is such a fantastic friend and caregiver to our pup “S”! Twice this year, we’ve taken trips of longer than a week. During both trips, Emmy stayed at our... (more)"

11. Kirsten

Loving care when you're not there!

Medford, MA, 02155

Drop-In Visits, Dog Walking

"I have been lucky enough to have kirsten watch my dog three times now. Every time i checked in with her, the dog was being carefully watched, walked, and or ... (more)"

12. Juanita

Woodland walks @end of road

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Juanita is the most loving and caring person. She has watched my dog for almost two years on and off and I think he likes her more than me now! She feeds... (more)"

13. Sarah

The Puppy Playhouse

Medford, MA, 02155

Dog Boarding, Doggy Day Care, Dog Walking

43 repeat clients

"Great! Sarah was great with my sometimes grumpy old pup, patiently working through his nervous growls with treats. :) . I will absolute use her for my furb... (more)"

14. Laura

Home full time

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Hello Pet Parents! I have known Laura C her whole life and watched as she developed her love for animals. She is kind, patient, responsible and really has a ... (more)"

Confirmed Memorial day Availability
15. William

Walk'n your best friend is an honor

Stoneham, MA, 02180

Drop-In Visits, Dog Walking

"I would definitely recommend William F. as a dog walker and dog sitter. William has been taking care of my dogs from time to time for the last couple years a... (more)"

Confirmed Memorial day Availability
16. Kevin

I’ll hike or run with your dog!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Kevin has always been great helping take care of my dogs, which I'm sure comes from being a caring dog owner himself. Even my grumpiest dog likes him. He's e... (more)"

17. 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)

18. Erin

I can be your dogs best friend.

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Erin is a smart, responsible, level-headed, hard working, caring and kind young lady. She has experience caring for aging grand parents, old people and anima... (more)"

19. Genta

Home full time - A Fuzzy Vacation

Stoneham, MA, 02180

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

28 repeat clients

"Genta has been walking our 6th month old pup daily for about a month. We love her! She always lets us know how Charlie did and sends great pics! (more)"

20. Heather

I’ll run with your dog!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

About: 1+ year of kennel experience with dogs of all sizes and temperments Past experience with house sitting and pet sitting for cats Nail trimming exp... (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.