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Dog Walkers in Windsor, MA

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

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1. Bryan

Dog lover with big farm

Averill Park, NY, 12018

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

"Bryan did an awesome job taking care of my puppy, Obi. He was very accommodating with my arrival time in the morning and Obi was always ready to go when I go... (more)"

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2. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

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

"I have had a wonderful experience with Heather watching my lovable and high energy golden retriever, Sadie. Heather really cares about animals and cares for ... (more)"

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3. Katie

Need a Furry Friend

Williamsburg, MA, 01096

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)"

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4. Laura

Heart-warming and friendly

Hatfield, MA, 01038

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

"Laura was so sweet and sent updates and pictures of my furbaby all day! I loved seeing how much fun she was having while I was at work. Thank you Laura! (more)"

Confirmed availability
4th of July
5. Ryan

The Doggie Dood - Pet Services!

Florence, MA, 01062

Dog Boarding, Doggy Day Care

"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)"

Confirmed availability
This weekend
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)"

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7. Sara

Dependable and Active!

Pittsfield, MA, 01201

Dog Boarding, Drop-In Visits, Doggy Day Care

"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)"

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8. Emma

Responsible, experienced dog lover!

Lee, MA, 01238

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

"Emma watched my 10 year old cockapoo Darby. She did a great job taking care of him. She took him for walks and was very loving. Darby has to take quite a bit... (more)"

9. Ava

Home full time - Parks nearby!

Williamsburg, MA, 01096

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

About: My name is Ava and I am a college student home for the summer. I’m hoping to buy a car soon and am looking to save up some money. Once I graduate I... (more)

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10. Dave

Experienced / flexible. Fun 4 dogs

Hatfield, MA, 01088

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

"I’ve never met a dog who didn’t love Dave. Dave is fluent in dog, and seems instantly able to calm even the most agitated pup. He’s also a clear communicator... (more)"

Confirmed availability
4th of July
11. Danielle

10 years of excellent dog boarding

Pittsfield, MA, 01201

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

About: My name is Danielle and I have been watching dogs forever. I managed a local dog daycare and boarding facility and spent 7 years managing the city... (more)

12. Mattie

Fun and friendly dog lover

Lee, MA, 01238

Drop-In Visits, Doggy Day Care, Dog Walking

"Mattie is amazing with animals! She can care for all sorts of different reptiles as well as dogs and cats. I would definitely recommend Mattie for pet sittin... (more)"

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13. Abigail

Walks and food makes everyone happy

Florence, MA, 01062

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

"Abigail is the best and most reliant dog walker! She is 100% reliable, conscientious and dependable! Her love of dogs is the icing on the cake! I high... (more)"

14. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

Doggy Day Care

"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)"

15. Kody

Reliable and flexible dog lover!

North Adams, MA, 01247

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

"Where do I begin. Kody is a special kind of person. A truely unique blend of kindness, care, and selflessness that isnt frequently found these days. I own a ... (more)"

16. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Ava-Lena is one of the few people in the world who managed to befriend our nervous little rescue dog--and many have tried! We have a two year old daughter an... (more)"

17. Valerie

Dog lover and home full time

Sunderland, MA, 01375

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

"Valerie is really caring and she has taken care of my sick dog before and she gave him so much love and attention. I feel comfortable leaving my dog with Val... (more)"

18. Nathan

I'll take your dog to the park

Weststockbridge, MA, 01266

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

About: I love animals I'm kind and friendly I am respectful and responsible. I will keep your dog happy and we will become friends. I've had dogs througho... (more)

19. Jeanne

Country setting, lots of hiking

pittsfield, MA, 01201

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

"Jeanne has cared for my dog Millie many times. She loves going there and playing with Stella (Jeanne's dog). There's a lot of room to play inside and outsid... (more)"

Confirmed availability
4th of July
20. Jason

Short fores hikes / village strolls

Williamstown, MA, 01267

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

"Jason is a great friend to animals. I have seen him personally rescue and rehabilitate a number of critters. He has watched my African Gray, cats and dogs wh... (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!