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

15 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. Elaine

Fun, lovable and flexible !

Chelsea, MA, 02150

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Elaine walked Chloe two times a day for 3 days while I was away. She is awesome! She took Chloe on long walks and sent tons of awesome photos. Chloe is a tim... (more)"

3. 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)"

4. Nikki

Dog's Bestfriend!

Medford , MA, 02155

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

3 repeat clients

"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)"

5. Joselyn

I'll ♡ your animal(s) like my own

Somerville, MA, 02143

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)"

6. Keri

Stay at home mom, loves dogs

Belmont, MA, 02478

Dog Boarding, Dog Walking

3 repeat clients

"Keri was great! Abbey had a great walk :) (more)"

7. Sophia

Loving, Responsible Dog Sitter

Somerville, MA, 02144

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

10 repeat clients

"Sophia is great. You can count on her to show up and give your dog a walk. If something does happen, she is very good at contacting you and keeping you up to... (more)"

8. Sofia

City-sleeping and trail-hiking!

Somerville, MA, 02143

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

15 repeat clients

"Sofia has been walking Yankee for the last three months and we can not be more happy with her,she is amazing! Thanks a lot Sofia!! (more)"

9. Sarah

Empathic and flexible dog lover

Somerville , MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah took excellent care of my schnauzer, Turbo. Beyond dogsitting for me, she and I also work together at the same hospital. She is a calm, warm, and respo... (more)"

10. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sara did an outstanding job with Charlie. She was able to walk her on extremely short notice. Dog was happy and in good spirits when we got home. She took ca... (more)"

11. Maxwell

Excited to meet new dogs in my area

Medford, MA, 02155

Drop-In Visits, Dog Walking

"My dog OG loved walking with Max! (more)"

12. Sarah

Experienced pet sitter & runner

medford, MA, 02155

House Sitting, Doggy Day Care, Dog Walking

"Sarah has been sitting for and walking my dog Bailey for many years. She is extremely responsible, caring, trustworthy and committed. I would highly recommen... (more)"

13. Frances

Kind Caring Dog Walker in Melrose

Melrose, MA, 02176

Dog Walking

"Frances has been a pet sitter for our 3 year old corgi. I could not think of a more loving and attentive dog caregiver (other than myself or my husband). F... (more)"

14. Mira

Doggydate:Eat, play, sleep, repeat!

Somerville, MA, 02144

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

"Mira was very kind and helpful! (more)"

15. Shannon

Nursing Student/Dog Lover :)

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Shannon is a dog lover. She's watched and cared for my dogs several times and always does a great job. I have 2 chihuahuas that take a while to warm up to pe... (more)"

Available this weekend
16. Natasha

While you're away your pet can play

Woburn, MA, 01801

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

About: Let me help you and your pet when every day life makes it hard to keep to the schedule. I do work full time but can ultimately provide drop in vi... (more)

17. 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)"

18. Julia

Experienced Professional Dog-lover

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

About: I have 2 dogs of my own, one small 11 year-old dachshund and one giant 3 year-old bull-mastiff. I'm no stranger to dealing with dogs of all sizes, ... (more)

19. Cameron

A life without dogs is not a life

Arlington, MA, 02476

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

1 repeat client

"Cam is truly fantastic with pets. Having lived in a home with three dogs for the past 4 years, his recent addition of a bunny is right at home at Cam's house... (more)"

20. Naomi

Flexible dog walking and sitting!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Naomi is one hundred percent trustworthy and dependable. She is kind and loyal, and will give your pet all the love it would have had if you were there too. ... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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.