Dog Walking in Winchester

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

1. Sophia

Loving, Responsible Dog Sitter

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

About: Hi! I'm Sophie and I graduated from the Rhode Island School of Design 2 years ago. I am a certified dog trainer (through Petco) and have worked wit... (more)

2. Beth

Full-Time Dog Lover!

Arlington, MA, 02476

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

"When I got my puppy I was struggling to find someone reliable to let him out while I was at work all day. After I hired Beth I didn't have to worry about tha... (more)"

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. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

5 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)"

5. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Sarah is a terrific dog sitter,walking and So sweet! She shows so much love to Bella! She also is very punctual. I highly recommend her,if she's free! (more)"

6. 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)"

7. Corinne

Fetch yourself a keeper!

SOMERVILLE, MA, 02144

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

2 repeat clients

"Corinne did a great job with our dog Norman. We will definitely be using her again in the future! (more)"

8. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

1 repeat client

"Nicole, is a fantastic pet sitter. She's very caring and wonderful with animals. I would recommend her and have to multiple friends for their pet sitting nee... (more)"

9. Christine

Teacher & Dog Sitter/Walker

Somerville, MA, 02144

Drop-In Visits, Dog Walking

3 repeat clients

"Christine was fantastic! Super responsive and gave me a full update on Enzo after their walk. I 100% would rebook with her and recommend her to anyone. (more)"

10. Meghan

Tufts University Dog Sitter!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Hello! I am looking to help out some families with dog sitting this summer and into the fall, so I thought this would be a perfect fit! I am very f... (more)

11. 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)"

12. 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)

13. Morgan

and Scup the Pup!

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"Ever since I met Morgan (15 years ago!), she has had a special place in her heart for animals. Since she lived at college and then living in an apartment in ... (more)"

14. Merrill

Rescue Dog Volunteer for Hire

Arlington, MA, 02474

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

1 repeat client

"Merrill was great. She came and met our dog before she started to take him for his walks. She took a few pictures and shared them with us. I would not hes... (more)"

15. 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)"

16. 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)

17. Rebecca

Dog and animal lover extrodinaire

Woburn, MA, 01801

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

About: I have over 30 years experience caring for dogs ands pets of all kinds. As of now I have a 5 year old Yorkshire Terrier. I have been caring for hi... (more)

18. Sam

Mutt owner who appreciates all dogs

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Sam has been taking care of our dog for the past couple of years. He looked after our dog during week-end trips and also over the summer when we went away fo... (more)"

19. 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)

20. 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)"

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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.