Dog Walking in Winchester

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

Confirmed available next weekend (Sep 29 - Oct 02)
1. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

11 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)"

2. Christopher

Active, Dog-Loving, Handyman

Cambridgeport, Cambridge, MA, 02139

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

1 repeat client

"Chris is punctual responsible and did a great job planning, executing and even followed up to see how Chaos was doing. I'll use him whenever we are in Boston... (more)"

3. 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)"

4. Maddie

Dog-loving graduate student

Watertown, MA, 02472

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Easy to work with and took amazing care of our puppy! (more)"

5. Claire

If I weren't a person, I'd be a dog

Riverside, Cambridge, MA, 02139

House Sitting, Drop-In Visits, Dog Walking

"Claire is a courteous and responsible person and a great dog-sitter! I always refer jobs to her when I can't take them because of her natural aptitude with a... (more)"

6. Kara-Jane

Reliable&Experienced Grad Student!

Allston-Brighton, Brighton, MA, 02135

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

6 repeat clients

"Kara-Jane is absolutely wonderful! From the second my puppy met her he fell in love. She is reliable, kind and always sends a picture from the walk! I would ... (more)"

7. Candace

Stay at home Dog lover

Woburn , MA, 01801

Dog Boarding, House Sitting, Dog Walking

1 repeat client

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)

8. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

3 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)"

9. Emma

Responsible, compassionate, fun!

Belmont, MA, 02478

House Sitting, Drop-In Visits, Dog Walking

"I , without hesitation, highly recommend Emma as a responsible and loving dog caregiver! My dogs are my beloved family members and have never been left in t... (more)"

10. Nancy

Vet Tech Dog Sitter, Dog Walker

Arlington, MA, 02476

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

2 repeat clients

"Nancy is incredible and I highly recommend her. She took such great care of Louie and even helped with training. She's a great communicator, is very thoughtf... (more)"

11. Allie

Grad student filling dog-less void

Watertown, MA, 02472

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

1 repeat client

"I have known Allie for eight years, and she is the most caring and compassionate animal lover I've ever met. She is highly responsible and is always looking ... (more)"

12. Sophia

Loving, Responsible Dog Sitter

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Sophie has taken great care of our labradoodle on multiple occasions for various lengths of time. She is super responsible, kind and caring. Our dog looks fo... (more)"

13. Bryna

Kind, Caring, Loves Walks

Malden, MA, 02148

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

1 repeat client

"Bryna adores dogs and they respond immediately to her passion. She's lived with and cared for dogs most of her life, and provides exceptional and skilled ca... (more)"

14. Laura

VET TECH with huge heart!

Somerville, MA, 02145

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"It's possible that my boyfriend and I are slightly obsessed and over-protective dog parents, so when it comes to leaving our pup, Cowie, (a 9 year old, 50lb ... (more)"

15. Shira

Vet Tech, Experienced Pet Caretaker

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Shira is an incredibly responsible and loving pet sitter. She has taken care of my pets repeatedly in the past, sometimes for months at a time, and has alway... (more)"

16. Lawrence

Energetic & Responsible

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Lawrence is a true dog lover! He has one of his own and daily feeds, walks, and plays with his dog Grace. He is constantly loved by many dogs, one of which b... (more)"

17. Casey

I will love your dog like my own

Woburn, MA, 01801

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

"My husband and I have used Casey on a number or occasions for dog walking & pet sitting services. She's fantastic. The dogs are exhausted after her walking a... (more)"

18. Andrea

Loving Pre-Vet Student

Medford, MA, 02155

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

1 repeat client

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)

19. Joann

Loving caring patient and generous

Medford , MA, 02155

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

About: You can ask my best friend how Well I took care of her dog. She was a beagle with some health issues , we all loved her and she loved us. Unfortun... (more)

20. Ashley

I am an active animal lover!

Arlington, MA, 02474

Drop-In Visits, Dog Walking

About: I am an avid runner and teacher who has grown up with dogs her entire life. As a child we bred and raised Jack Russell Terriers. I love all animals... (more)

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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.