Dog Walking in Winchester

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

1. Tegan

I'll Be Your Dog's Best Friend

Somerville , MA, 02143

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"We love having Tegan walk our dog, Louie! Tegan is very courteous and considerate. She's quick to reply to our inquiries about booking and answer questions... (more)"

2. Emma

Responsible, compassionate, fun!

Belmont, MA, 02478

Drop-In Visits, Dog Walking

"I , without hesitation, highly recommend Emma as a responsible and loving dog caregiver! My dogs are my beloved family members and have never been left in t... (more)"

Available this weekend
3. 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)"

4. Robyn

Patient, Great With Puppies

Winchester, MA, 01890

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

2 repeat clients

"I can't recomend Robyn enough! She came to the rescue when our 10 month old pup needed a last minute sitter and did an excellent job at monitoring him and ke... (more)"

5. Andrea

Loving Pre-Vet Student

Medford, MA, 02155

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

5 repeat clients

About: I moved to MA to attend the Cummings School of Veterinary Medicine at Tufts University. I'm a 100% dog lover. Growing up always took care of my do... (more)

6. Victoria

Very caring and outgoing

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Victoria is very sweet and the dogs love her. She was right on time and even did my husband a favor and walked them to the groomer dice he didn't feel well! ... (more)"

Available this weekend
7. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

"Nicole has watched my two english bulldogs several times for short and long periods of time. She is caring and reliable and has always provided a great servi... (more)"

8. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Sarah was available to ease my mind as this was the first time we needed a dog walker in the 6 years we have had our dogs. She sent pictures and updates dai... (more)"

9. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Samantha was super responsive to our last minute needs, and coordinated time to walk our golden retriever on short notice. On scheduled days, she's easy to c... (more)"

10. 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)"

11. Candace

Stay at home Dog lover

Woburn , MA, 01801

Dog Boarding, House Sitting, Dog Walking

2 repeat clients

About: Hi there! My name is Candace. I live with my parents in Woburn, MA and I work from home. I am and always have been an animal lover! My family has a... (more)

12. Channah

I'll treat your dog as my own!

Cambridge Highlands, Cambridge, MA, 02138

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"We really appreciated how Channah took care of our Monty. She did a great job and he always seems excited to see her in the photos that she shares. Thanks fo... (more)"

13. Mary

Love dogs more than I love people.

North Cambridge, Cambridge, MA, 02140

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

2 repeat clients

"Mary did an awesome job walking our 6 month old Bernese pup! She was quick to respond and very flexible scheduling a meet and greet. Already have her booked ... (more)"

14. Nancy

Vet Tech Dog Sitter, Dog Walker

Arlington, MA, 02476

Drop-In Visits, Dog Walking

2 repeat clients

"Nancy is incredible and I highly recommend her. She took such great care of Louie and even helped with training. She's a great communicator, is very thoughtf... (more)"

Available this weekend
15. Andrew

Athletic and chill, love animals.

Arlington , MA, 02474

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

About: I have never owned a dog but I have always loved them and treated them with kindness. A renown petter to any dog I have ever met. I understand how ... (more)

16. Kiah

A very patient lover of all animals

Stoneham, MA, 02180

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

About: Hello, my name is Kiah and I am an animal loving student from Umass Amherst :) I have had my dog for 5 years now, so I am very used to caring for d... (more)

17. Nina

Responsible student loves dogs!

Medford, MA, 02115

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

"Nina is a very responsible dog owner and caregiver. She has tons of love and care that she gives her dog at home and I'm sure that she'll bring that passion ... (more)"

18. Aline

Dog-loving student by Davis Square!

Medford, MA, 02155

Dog Boarding, Doggy Day Care, Dog Walking

"Aline has grown up with a dog at her parents home and is one of the most caring, responsible people I know. She has dog sat in the past for friends and has ... (more)"

19. Colin

I love dogs, walks, and playtime!!!

Medford, MA, 02155

Drop-In Visits, Dog Walking

2 repeat clients

"Colin has been great! He is very responsive, reliable, and I know my dog just loved going on walks with him! (more)"

20. Merrill

Rescue Dog Volunteer for Hire

Arlington, MA, 02474

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

"I could not recommend Merrill more to care for your pets! Not only is she trustworthy, reliable, and responsive, but she will love your animals almost as muc... (more)"

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Learn About Premier

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.