Dog Walkers in Windsor, MA

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

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Confirmed availability
Christmas and New Year
1. Bethany

Friendly experience pet lover

Cheshire, MA, 01220

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

"Bethany has watched my dog several times. She always gives Luna the full attention that she needs which is tough because Luna is a high energy husky. Bethany... (more)"

Confirmed availability
Christmas and New Year
2. Jeanne

Country setting, lots of hiking

pittsfield, MA, 01201

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

"5 stars is not enough to describe how wonderful Jeanne is. She gave great care to Romeo and was a fantastc dog sitter. My dog really loved her. I would highl... (more)"

3. Heather

Large Fenced Yard - Flexible Hours

Pittsfield, MA, 01201

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

"Heather was kind and accommodating. We got several pictures of our pup throughout the day. (more)"

Confirmed availability
Christmas and New Year
4. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

"Kelsey watched our pup for the day while we were in Lenox and they had a great time :) Thanks so much Kelsey - will definitely reach out again next time we’r... (more)"

5. Jennifer

I’m Happy keeping your dog happy

Pittsfield, MA, 01201

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

"Jenni has bin helping me with my 8 year old dexter a Doberman for five years now and I wouldn’t change her for anyone. I can trust that in her care he will r... (more)"

Confirmed availability
Christmas and New Year
6. Erin

Let's go for a walk

Florence, MA, 01062

Drop-In Visits, Doggy Day Care, Dog Walking

"I highly recommend Erin for any job having to do with caring for dogs. She is AMAZING, reponsible, loving to dogs, and simply an absolute pleasure to work wi... (more)"

Calendar Recently Updated
7. Katie

Endless love and affection!

Goshen, MA, 01032

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

"I highly recommend Katie as a dog sitter for she is one of the most mature, responsible, hardworking individuals I know, with a commitment and drive for exce... (more)"

8. Sara

Dependable and Active!

Pittsfield, MA, 01201

Drop-In Visits, Doggy Day Care, Dog Walking

"Sara is a very caring and kind person and Madge loved spending time with her. You can feel the positive energy when you meet Sara and that flows straight to... (more)"

9. Melani

Vet Student for Your Furry Friend

Williamstown, MA, 01267

Dog Boarding, Doggy Day Care, Dog Walking

"Melani was terrific. She was super accommodating on drop-offs and pick-ups, and our pup, River, took to her immediately. You can tell that she's an experienc... (more)"

Confirmed availability
Christmas and New Year
10. Sarah

Doggy Lover thats home full time

Pittsfield, MA, 01201

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

"Awesome! (more)"

Confirmed availability
Christmas and New Year
11. Ryan

The Doggie Dood - Pet Services

Florence, MA, 01062

Dog Boarding, Doggy Day Care

"This was our first stay with Ryan and it went very well. I could tell Bean got plenty of exercise playing with all the other dogs and was well cared for. ... (more)"

Calendar Recently Updated
12. Missie

I'll run with your dog!

Leeds, MA, 01053

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

"Missie is great with dogs! She's completely up for running and playing around and has a lot of energy. I've had her walk my own dog a handful of times and sh... (more)"

Confirmed availability
Christmas and New Year
13. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Samantha is a very dependable, friendly, and caring person, who really took great care of our 3 dogs when we went on vacation. Whether it was just for the we... (more)"

14. Barbara

I have had dogs for the past 25 yea

Lee, MA, 01238

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

About: I am also a professional dog groomer for the past 20 years. Can give your dog a bath or a grooming if you'd like. Love walking with dogs and also c... (more)

15. Catherine

Doggy Trails is where we like to Go

New Lebanon, NY, 12125

Dog Boarding, Drop-In Visits, Doggy Day Care

"Catherine is great with all animals but most importantly with dogs!!! I have 6 dogs and it's always been a challenge to find a pet sitter that is trustworthy... (more)"

Confirmed availability
Christmas and New Year
16. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

"Our puppy had so much fun with Kristin and her family, including her dog. Playing all day and spending lots of time outside was great for our dog. Kristin wa... (more)"

Confirmed availability
Christmas and New Year
17. Kathleen

Experienced pet sitter and hiker!

Conway, MA, 01341

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

"Kathleen is excellent - knowledgeable, friendly, caring, and I love how active she is with our puppy! She sends great updates throughout the day, and is eas... (more)"

18. Matt

Home all hours of the day most days

STEPHENTOWN, NY, 12168

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: I have had dogs all my life and also have been a dog showman in my younger days participating in dog shows both with the local 4-H program and othe... (more)

19. Caroline

I’ll run, walk, skip, w/ your dog!

Ashfield, MA, 01330

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

About: I am a very attentive pet-sitter with a love for dogs of all shapes, personalities, sizes, and breeds. While I’m a very active person that enjoys l... (more)

20. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Ava is not just a good pet-sitter but an EXTRAORDINARY one. I've know her for 20+ years and when she was still in high school my husband and I entrusted her... (more)"


When you need dog walking services, we doubt you'll find a better experience than through Rover. Thanks to our wide selection of dog walkers in Windsor, MA, you'll find that you're able to work with a dog walker who fits in with you, your dog, and your needs. With our start-to-finish approach, your walker can supply you with real-time dog walking updates with start and stop times, a GPS map of their walk, info about any bathroom, food, and water breaks, and pictures of what your dog's been up to. And on top of that, each Rover dog walking booking includes premium pet insurance, 24/7 support, and a reservation guarantee.

Looking for a quick solution to your dog walking needs when you're short on time? Then you'll love the Rover dog walking app. The Rover app features hundreds of highly rated, trusted dog walkers, and you can scroll through the options or simply rebook your regular dog walker in seconds. Your dog walker can share real-time photo updates via the Rover dog walking app, and with the app's cashless payment feature you'll be able to compensate your dog walker quickly and safely - no need for cash, checks or tips.

Speaking of payment, the cost of dog walking in Windsor, MA may surprise you - in a good way. That's because there's a dog walker on Rover for nearly every price range and lifestyle. Curious about how much you can expect to pay for dog walking on Rover? Check out our average dog walking rates to get an idea before you start a conversation with an individual dog walker.

When you need dog walking services in Windsor, MA, you'll be amazed at how easy it is to find the ideal dog walker with Rover.com. We take the guesswork out of selecting the perfect Windsor dog walking services for your needs. The dog walkers listed on Rover have been reviewed and approved, and - most importantly - they love dogs. In fact, 95% of reviewed stays and walks have a perfect five-star rating. When a dog walker in Windsor, MA joins our site, they complete a background check. You'll be able to see that they've passed the background check when you view their individual dog walker profile. No matter what level of support you're looking for, you're sure to find a great fit for all your dog walking needs in Windsor, MA with Rover's dog walking services, whether it's a one-time emergency or a daily appointment.

In short, when you use Rover to find a dog walker in Windsor, you can rest easy knowing that your dog is having a great time.

Do you think you have what it takes to become a dog walker for Rover? We're always looking for people with a passion for dogs to join us as a dog walker! If you've been thinking about starting up your own dog walking business, or even if you've been doing it on your own for a while, you'll want to check out our easy sign-up process and consider joining the hundreds of awesome dog lovers who use the Rover dog walking platform. When you become a Rover dog walker, you get access to great support, including premium pet insurance, cashless payment (no more worrying about whether you'll get paid on time), and a third party background check to demonstrate your trustworthiness to prospective clients. Join our pack today!