Dog Walkers in Chester, MA

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

1. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"My dogs love Charlie-Marie. She has been dogsitting them for 2 years now. I feel bad leaving them during the day while I am at work or when I go on vacation... (more)"

2. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

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

"I have known Amanda for 15 years now, and she is the most compassionate animal lover I know! She is very empathetic towards animals and is very protective o... (more)"

3. Luke

3/5 barn builder, 2/5 dog walker

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: Hey! I'm Luke! I've cared for dogs all my life. My dog now, Chai Chai, is a sassy princess but we all still love her. Honestly, I can't have enough... (more)

4. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

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

"It is my pleasure to recommend Melissa as a caregiver for your furry family member/s. Her care and consideration for an animals individuality and needs is ex... (more)"

5. Molly

Responsible and caring

Granby , CT, 06035

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I am so happy to write a testimonial for Molly H. We have a 14 year old Italian Greyhound who is as dear to us as our 2 legged children. Denali has never b... (more)"

6. Victoria

I go above and beyond, every time.

Westfield, MA, 01085

House Sitting, Drop-In Visits, Dog Walking

About: For over 8 years, I have cared for all ages, sizes, breeds, and temperaments of dogs. Keeping your pet happy, healthy, comfortable, exercised, fed,... (more)

7. Rachael

Full time student part time dog nut

Cheshire, MA, 01225

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

5 repeat clients

"Rachael was very accommodating and willing to take on my Sadie for a few in the middle of the day and evening, fitting my dog into her schedule with very lit... (more)"

8. Kelly

Runner who loves dogs!

holyoke, MA, 01040

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

7 repeat clients

"Kelly and her husband do a great job Bleu always comes home happy and tired out from all the fun he has with them (more)"

9. Ryan

The Doggie Dood - Pet Services!

Florence, MA, 01062

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

4 repeat clients

"Excellent care. Maya really loved her time with Ryan and especially with his dog, Willow! She was quite happy and tired when I got her home. (more)"

10. Steve

I am a retired teacher/dog owner

Enfield, CT, 06082

Dog Boarding, Drop-In Visits, Doggy Day Care

14 repeat clients

"My dog loves going to Steve and Deb's. He gets so excited and runs right in. They take such good care of him and treat them like their own. They also are ver... (more)"

11. Charlie-Marie

Ambitious and active dog sitter

Pittsfield, MA, 01201

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

"In the 7 years I have known Charlie, she always had a strong passion for animals, especially dogs. She can't pass by one at the store or out in public wit... (more)"

12. Tammy

Dog loving family

Westfield, MA, 01085

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

4 repeat clients

"The whole experience was great. Tammy was easy to communicate with and Buddy was happy upon pick up. Next time I am in the area and require a dog sitter I ... (more)"

13. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

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

"Amanda is a very caring person who loves animals . As a child she took care of her horse , dog & her cat . She has been house sitting for us for five years n... (more)"

14. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

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

"Great dog sitter! Melissa cared for our dog in her home for nearly two weeks and we were very pleased with the attention and care that she provided. She has ... (more)"

15. Brittany

Loving, responsible & attentive!

Pittsfield, MA, 01201

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

1 repeat client

"Brittany was super sweet and very accomadating! My puppy was happy and well cared for ? (more)"

16. Desiree

Animals always come first! (;

Easthampton, MA, 01027

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

"Desiree is one of the most passionate person when it comes to animals!! Especially dogs!! She will give them more than 100% attention and keep that tail wagg... (more)"

17. Sandra

looking to love some little doggies

Chicopee, MA, 01020

Dog Boarding, Drop-In Visits, Doggy Day Care

"I am Sandra’s mother and growing up we always had dogs. Sandra was always great with our dogs and even when she moved out on her own she often took care of o... (more)"

18. Lindsay

Past dog trainer, forever dog lover

Enfield, CT, 06082

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

"I have left my dogs in Lindsay's care on several occasions. They were always well cared for. She did a competent and professional job. I have complete confid... (more)"

19. Shawn

1 on 1 care and fun for your pup

AGAWAM, MA, 01001

Dog Boarding, Doggy Day Care

"My dog loves going to Shawn's house! Remy is a difficult dog to handle since he is a 2-year old boxer (a.k.a a 60 lb ball of energy) but Shawn was so welcomi... (more)"

20. Laura

Dog loving family, works from home

Westfield, MA, 01085

Dog Boarding, Doggy Day Care

1 repeat client

"Laura and her family have been AMAZING dogsitters for my 3 dogs over the past 8 years. They truly take care of my dogs as if they were their own. They even... (more)"

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Learn About Premier

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 Chester 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 in Chester 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.