Dog Walking in Winchester

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

1. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

8 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)"

Available this weekend
2. Andrew

Compassionate Animal Lover!

Reading, MA, 01867

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Andrew is a kind, gentle and responsible person. His love of all living things is evident in his dealings with animals and their humans. He loved taking my d... (more)"

3. Joselyn

I'll ♡ your animal(s) like my own

Somerville, MA, 02143

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Joselyn is great with our dog. She is very warm and understanding. She is happy to accommodate our routine and requests. She is very communicative, asking an... (more)"

4. Sophie

I spoil your dog like my own!

Reading , MA, 01867

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

43 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)"

5. Nikki

Dog's Bestfriend!

Medford , MA, 02155

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

"Nikki was enthusiastic. Was on time and took Charlie for a good solid walk. I would absolutely have Nikki walk my dog again. Ask good questions about her and... (more)"

6. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

7. 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)"

8. Cheryl

Lets Doggie Party!

Burlington, MA, 01803

Dog Boarding, Doggy Day Care, Dog Walking

26 repeat clients

"Cheryl is exceptionally qualified to be a dog sitter. Very caring, detailed and reliable. She has had many dogs, assisted with ours and many other friends. S... (more)"

9. Jessica

I'm trustworthy and passionate

Malden, MA, 02148

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

1 repeat client

"Jessica is a wonderful caregiver for pets. She is loving and attentive. I would highly recommend her for anyone's companion. Jessica is spectacular at tak... (more)"

10. Gretchen

Woof, Woof, Woof!

North Cambridge, Cambridge, MA, 02140

House Sitting, Drop-In Visits, Dog Walking

4 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)"

11. 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)"

12. 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)"

13. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

6 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)"

14. 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)"

15. Lawrence

Energetic & Responsible

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hello Lawrence loves dogs. He helped raise our Border Collie/ Mix from a 4 month old pup until we lost him at age 15. His sister adopted a puppy shortly... (more)"

16. Luciana

Join the pack

Medford , MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Luciana has known my dog, Elsa, since she was a puppy. Luciana's dog Xiina and Elsa often have play dates. Luciana seems to have a special connection with t... (more)"

17. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

15 repeat clients

"Great experience with Sarah, she was prompt in her response booking a dog walking and was willing to travel a little further than usual to accommodate us in ... (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. Jennifer

Dog Walking Done Right

malden, MA, 02148

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

1 repeat client

About: I went to school for law enforcement and graduated in 2012 with my Associates Degree. I always wanted to work with animals, and most importantly do... (more)

20. Megan

Must Love Dogs

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Megan would be an ideal choice for your pet sitting needs. She has two dogs of her own and her care and attentiveness for them and every other animal that sh... (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.