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

8 repeat clients

"Really appreciate Beth taking Baron out for mid day romps. She's been a huge help - super responsive, really great with Bman, and 100% reliable & professio... (more)"

2. Alessandra & Jennifer

WE❤ALL FUR BABIES (PLEASE READ ALL)

Everett , MA, 02149

Dog Boarding, Drop-In Visits, Dog Walking

19 repeat clients

"Jennifer is great! She's reliable, prompt and pleasant to work with. I can see how she has bonded so well with Crimson, my dog. I feel comfortable recommend... (more)"

3. Eva

Enthusiastic/responsible dog lover

Somerville, MA, 02143

Dog Boarding, Doggy Day Care, Dog Walking

3 repeat clients

"Eva is an absolutely fabulous dogwalker -- thoughtful, reliable, and wonderful with our pup. Would highly recommend to anyone! (more)"

4. Noah

Responsible lover of all dogs

Somerville, MA, 02145

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Noah was available last minute to walk my dog when I had a scheduling conflict and saved me a lot of stress! He arrived within the preferred time slots and ... (more)"

5. Chris

Dog lover extraordinaire!

Watertown, MA, 02472

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

3 repeat clients

"Chris is very reliable and took great care of my mini Schnauzer, Lulu. I would absolutely recommend him and will not hesitate to book him again! (more)"

6. Olivia

Responsible, animal adoring vegan.

Allston-Brighton, Allston , MA, 02134

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Olivia is wonderful! Our dogs loved her! She was very dependable! (more)"

7. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

4 repeat clients

"Nicole did an excellent job with Charlie. Sent videos, and a picture. She met Charlie the day before, and she was able to step in on short notice. A huge hel... (more)"

8. Sophie

I spoil your dog like my own!

Reading , MA, 01867

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

39 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)"

9. 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)"

10. Kailey

Life is ruff! I can make it easier

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Dogs really liked Kailey. She is nice young lady who was great with my puppies! (more)"

Available this weekend
11. Gretchen

Woof, Woof, Woof!

North Cambridge, Cambridge, MA, 02140

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Gretchen was wonderful and really flexible! Maggie really enjoyed her walk and I appreciated the detailed description of the walk and Maggie she gave! I wou... (more)"

12. 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)"

13. 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)"

14. 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)

15. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"I just moved to Boston from Ohio and I travel semi-frequently for work. Back in Ohio I have family who would watch my dogs while I was traveling. I have two ... (more)"

16. 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)"

17. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

15 repeat clients

"When I say Sarah's name,that she's coming ,Bella collects all her toys to bring to her! She adores the outings and comes back bouncing or so tired Bella runs... (more)"

18. Christine

Teacher & Dog Sitter/Walker

Somerville, MA, 02144

Drop-In Visits, Dog Walking

4 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)"

19. Andrew

I Know How Dogs Think

Somerville, MA, 02144

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

1 repeat client

"my dog Alfie loves spending time with Andrew! I was always comfortable leaving him with him when I travelled for work. Even though Alfie sometimes has a tem... (more)"

20. Megan

Must Love Dogs

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Meg was a great sitter for my little yorkie, Seamus! I could tell she loves dogs and knew exactly how to make them happy and well cared for. She was easy to ... (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.