Dog Walking in Winchester

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

1. Beth

Full-Time Dog Lover!

Arlington, MA, 02476

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

5 repeat clients

"Beth is great. We did a meet and greet and showed her how our puppy reacts. We do have special walk instructions for one pup and she was so nice about it (d... (more)"

2. Casey

Experienced Veterinary Technician

Malden, MA, 02148

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

About: My name is Casey, I am 24 years old. I had been working as a veterinary technician in New Hampshire for 4 years and had been a volunteer at my loca... (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. Nina

Responsible student loves dogs!

Medford, MA, 02115

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

1 repeat client

"Nina is a stellar dog sitter and walker! She has so much love and tenderness for all the dogs she works with. She is punctual, responsible, and trustworthy -... (more)"

5. Meagan

Former groomer and dog enthusiast!

Medford, MA, 02155

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

4 repeat clients

"She's great! We have a new puppy and love having her stop by for a walk mid-day (more)"

6. Andrea

Loving Pre-Vet Student

Medford, MA, 02155

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

7 repeat clients

"Andrea is very friendly and comfort with Simon. Simon after only 3 visits is excited to see Andrea and go for a walk. (more)"

7. Sophie

It's a Ruff Life!

Reading , MA, 01867

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

38 repeat clients

"Sophie is amazing! We just started with Sophie recently, and we are planning to use her long term for my dog Hunter. Hunter seems to love her so far, and i... (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

3 repeat clients

"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. 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)"

10. 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)"

11. 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)

12. 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)"

13. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Sarah did an excellent job giving our energetic pup exercise during a few days. She arrived as agreed each day, and sent clear pictures from their walk. Hap... (more)"

14. Christine

Teacher & Dog Sitter/Walker

Somerville, MA, 02144

Drop-In Visits, Dog Walking

3 repeat clients

"Christine was great! It was a last minute booking (normally dog comes to work and couldnt) and Christine was super accommodating. I loved getting a pic of my... (more)"

15. 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)"

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. 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)

18. Ali

<3 Cats & Dogs!

Medford, MA, 02155

Drop-In Visits, Doggy Day Care, Dog Walking

"Ali and I are coworkers and last year I unintentionally ended up with two puppies (who I love and wouldn't trade for the world, but was not prepared for). On... (more)"

19. Andrew

I Know How Dogs Think :)

Somerville, MA, 02144

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

"Andrew has been nothing but spectacular in the care of his dog Luna. Luna is a well trained pooch who benefits from Andrew's love and affection. Andrew has a... (more)"

20. 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)"

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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.