Dog Walking Winchendon

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pet parents in Winchendon have booked dog walking

Winchendon, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Jorden A.
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Jorden A.
Star Sitter
$25
total per walk
5.0 out of 5 stars
• 98 reviews
19 repeat clients
17 years of experience
Rindge, NH, 03461

“Jorden is great with our dog Winston. Jordaen really takes the time to work with Winston on things he is still learning and Jorden let's us know Winston's growth. I would recommend Jorden. ☺️🐶”

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Amy P.
Sitter Profile Image: Amanda H.
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Amanda H.
Star Sitter
$39
total per walk
5.0 out of 5 stars
• 76 reviews
23 repeat clients
15 years of experience
Winchendon, MA, 01475

About: 🐶Insured through The Hartford 🐶IAP Certificate-Dog Daycare Ownership 🐶Fear Free certified 🐶Red Cross Pet CPR + First Aid certified 🐶Daily updates with photos and videos of your fur babies playing and having fun 🐶Off-site hikes and pup adventures with pet parent's approval 🐶Cage free unless specifically requested 🐶Fenced in Dog area off the back deck 🐶Enrolled in grooming classes (in progress) 🐶Experienced in administering both oral and injectable medications 🐶Comfortable handling animals with special needs or following special requests 🐶Small limits of 4 boards at a time and only with pets I already know well that will get along with new pets visiting. I want all pets to be safe and receive all the attention they deserve. Open to discussing individual situations if you aren't comfortable with groups! I am a stay at home mother and pet care is a huge aspect of my daily routine. Where I am home basically all day every day, your pet will always have a watchful eye on them and plenty of love and attention. My two corgis will be out and about and are dog friendly. If I should need to step out I have a Furbo pet camera and crating is an option if that is the owner’s preference. Dog daycare days though I will prioritize being in the home for the day outside of my child drop off and pickups just downtown from me. We have a partially fenced in property so dogs can run free in the gated fenced in area or can be strictly walked and played with on leash- owner preference.

Sitter Profile Image: Danielle K.
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Danielle K.
$30
total per walk
4.8 out of 5 stars
• 35 reviews
9 repeat clients
20 years of experience
Templeton, MA, 01468

“Dani is AWSOME. She was very patient with my mini schnauzer Toby.He likes to sniff everything and gets upset with other dog walkers when they rush him. She brought her dog Greyhound Zeke who is well behaved and adorable.”

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Jason V.
Sitter Profile Image: Kae L.
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Kae L.
$23
total per walk
1 repeat client
15 years of experience
Fitchburg, MA, 01420

About: Let me bring your dog on an adventure - my dog walks start at $20 but I do hikes on a sliding scale. I have group play experience, I can bring your dog to a dog park without any fear that your dog will get into any sort of trouble. I'm a quiet, clean, petsitter, I will likely leave your house cleaner than it was when you let me in. "I have worked with Kae, of Little Lyons, for about a year. He is contentious, dedicated, and loving to all the people and pets he comes into contact with. I highly recommend his services and happily look forward to working with him again in the future." - Nicole E. "Kae dogsits for me when I go away on business trips or go into Boston for the weekend, and I could not recommend him more highly! He is caring and attentive to my dog; my dog gets so excited to see him. My dog is medium to high energy and Kae always tires her out. He is extremely knowledgable about dogs and dog behavior and has given me several tools to help keep my dog more mentally engaged and less stressed. Kae is punctual, he remembers all sorts of details about every dog, and he is my go-to whenever I need someone. Best dog sitter/walker in the Providence area!" - Kate R. I have worked with a doggy daycare, where I learnt dog behavior, and positive reinforcement training. I have worked in home pet sitting for dogs, cats, rabbits, snakes, tortoises, geckos, bearded lizards, salt and fresh water fish, for over a decade. Schedule a meet and greet with your pets! LGBTQIA+ friendly, Disability and Sensory Friendly I have kept strange hours for a very long time. I can fit your furry (or scaly or feathered) family into my schedule without issue. As a pet service professional, I like to make sure your pet is well attended to, and you feel as safe and comfortable as they do. I enjoy waking up to walk a client's dog, or making sure your cat feels safe before it's time to turn the lights off. You can rest assured while I am with your pets that they will be well attended to. A typical visit includes 15-20 minutes of play with your pet depending on energy levels, lots of positive attention and love, feeding and making sure they have access to water and making sure any business is done. As an overnight visitor, often for pets with anxiety or special needs/senior pets, I am with your pet in your home from 10pm-8am, plus visits during any of their usual scheduled feedings. As a dog walker, you can expect me to arrive and provide a full 30 minute walk to your pet. If you book through rover, you can also get a map of the walk we did, how long it took, and I provide pictures along the way. When it's time to go home, I make sure they and your home are safe and secure.

Sitter Profile Image: Colin P.
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Colin P.
Star Sitter
$34
total per walk
5.0 out of 5 stars
• 100 reviews
21 repeat clients
15 years of experience
Fitchburg, MA, 01420

“We love Colin! He takes such amazing care of my puppy Vincent and my dad said he is always so impressed at how patient and kind he is even when the puppy attitude comes out. Thank you Colin!”

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Stephanie G.
Sitter Profile Image: Apple R.
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Apple R.
$27
total per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
6 years of experience
Leominster, MA, 01453

About: I have had pets since I was 3 years old. I really started to get involved with pet care when I was a preteen. I have done pet sitting with my friends as well. I am going to college to study veterinary technology and am looking to get more hands on experience with dogs and cats! :) ⚠️PLEASE READ BEFORE REQUESTING⚠️:I am currently working part time, so I have plenty of time to watch your pets during the week. However, I may have to leave a few hours a day to go to work! I am able to stay overnight any time. I have a fenced in back yard and I can crate the dogs if needed. I have leashes and harnesses in my home. Everything in my home is pet proofed.

Sitter Profile Image: Patricia H.
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Patricia H.
$28
total per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
40 years of experience
Princeton, MA, 01541

“Pat was fantastic with my 7 month old puppy who is full of beans! She always came as planned and I could tell that he'd had the company and exercise!”

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Jennifer G.
Sitter Profile Image: Kyle G.
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Kyle G.
$17
total per walk
10 years of experience
Westford, MA, 01886

About: I have been pet sitting for 10 years, I board and do in home visits, I sit for dogs, cats, small mammals, reptiles and even fish! I prioritize animals safety while also providing proper enrichment, walks, hikes, playdates, and play sessions. I am also a Certified veterinary technician. I currently work at a doggy daycare, on days off i'm with pets all day walking and playing. During work days I walk dogs before work and then get a 3 hour break in the middle of the day where I hike with dogs and cats. I have a fenced yard and a friendly cat and a friendly dog at home to keep your pets company. I find hiking trails and safe walking routes to take pets on fun adventures!

Sitter Profile Image: Majdoline B.
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Majdoline B.
$17
total per walk
5.0 out of 5 stars
• 43 reviews
20 repeat clients
20 years of experience
Concord, MA, 01742

“Majdoline has been awesome from the moment I reached out! Super responsive, always on time, and my pup loves her. My dog can be a bit quirky, but Majdoline handles him really well. Would highly recommend booking her!”

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Daniel M.
Sitter Profile Image: Erinn O.
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Erinn O.
Star Sitter
$56
total per walk
5.0 out of 5 stars
• 12 reviews
3 repeat clients
20 years of experience
Holden, MA, 01520

About: With more than 20 years of experience in veterinary medicine and professional pet care, I bring a unique level of expertise, reliability, and compassion to every pet I serve. Throughout my career, I have worked closely with veterinarians and veterinary technicians, providing trusted pet sitting services for colleagues and clients alike. My extensive background ensures that your pets are in knowledgeable and capable hands at all times. I have successfully completed multiple background checks, reflecting my commitment to professionalism, integrity, and trustworthiness. I am also Fear Free Certified, which means i have advanced training in recognizing and reducing fear, anxiety, and stress in pets – allowing me to provide care that prioritizes both their physical and emotional well-being. Safety is always my top priority. I am certified in CPR fo humans, cats, and dogs, and I am highly experienced in administering a wide range of medications, including oral, injectable, transdermal, and subcutaneous treatments. Whether your pet requires routine care or more specialized medical attention, I am fully equipped to meet their needs with confidence and precision. Beyond medical care, I am dedicated to enriching your pet’s daily life. I prioritize meaningful interaction, socialization, and appropriate physical activity to ensure your pet remains happy, healthy, and engaged while you are away. Above all, I take great pride in being dependable, detail-orientated, and deeply respectful of the trust my clients place in me. I care for every pet as if they were my own, providing peace of mind and exceptional care you can rely on. I work full time at a veterinary hospital so if I'm pet-sitting your dog(s), I'll usually bring them with me to work with my dog. They have a fenced in yard where they can play during the day. If they are not social, they will just go out by themselves. If I'm watching your cat at your house, I will spend time with them around my work schedule, I will not subject them to daily trips in the car :) I have a fenced in yard and take frequent leash walks around my quiet and safe suburban neighborhood. We also love to hike if your pet is into that. Otherwise, your pet's needs dictate what I offer to them. If I'm watching them at your home, I try to stay to their schedule as much as possible.

Sitter Profile Image: Hillary L.
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Hillary L.
$23
total per walk
5.0 out of 5 stars
• 3 reviews
7 years of experience
Marlborough, MA, 01752

About: I have been taking care of our bull dogs for seven years now. We adopt and had three before our oldest recently passed away. Bull dogs provide quite a bit of high maintenance care such as cleaning all folds multiple times a day, tail pockets, monitoring skin for yeast or allergies and of course… wiping butts after potty time. At least two walks or forms of exercise a day to keep them in shape for their health and breathing issues; if you see my babies photos, they are in super shape! So caring for three I feel shows my love, responsibility, managing skills and understanding of how to properly and lovingly care for pets. For many years now, I have also cared for a variety of my family members dogs and cats, whether that involves feeding, walking/ exercise, over nights, and loving attention. I am Corporate Life Coach & Counselor so I have a flexible schedule that I make myself, in a variety of towns in Massachusetts ( which is why my radius is so big) I also have a rental house in Dennisport MA, so providing pet care in the Cape is an option too! I love my fur-babies and providing love, exercise and quality time is what your pet deserves too! I will be providing services at your household, so any and all safety protocol will be provided that suits you and your pet to the fullest!

Sitter Profile Image: Kim K.
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Kim K.
$34
total per walk
5.0 out of 5 stars
• 8 reviews
2 repeat clients
1 year of experience
Marlborough, MA, 01752

About: I just left my job after many many years. I worked in the addiction recovery sector. I have found myself still having so much in my heart to give I am retired and home so while I am babysitting your fur baby I will be sure to schedule things remotely. That way he or she will get the attention they need while you are away I take dogs on a walk regularly on a leash. Also, there is lots and lots of love to go around here for your fur baby while yo are away.

Sitter Profile Image: Jill K.
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Jill K.
$34
total per walk
5.0 out of 5 stars
• 8 reviews
5 repeat clients
40 years of experience
Upton, MA, 01568

About: My very friendly little dog and I would love to host your dog here with us, up to 40 pounds only though...Or if your pal would benefit from a playmate, we would love to come sit for you! Well first off, I've been trusted with the care of many precious pets for years now...And enjoy it very much...I am fun, caring, and engaging, as well as all ble's, reliable, dependable, and responsible! And I took a CPR pet course, and human one as well. I have had cats mostly all my life, and now own a small dog of my own, who as I stated earlier, could, or doesn't have to if need be, come with me, as some love to have a playmate for their pet...And I know my friendly little guy very much enjoys the visit. But with anyone coming to my home, my guy will be there too, and they must all be friendly, and then we have nothing but a good time. Which brings me to, I can watch any animal, esp in the animals home and of any size...It is my home that, as also mentioned above, I would only be able to take in a small or medium sized dog, cat, or caged pet. And my home, that I live in with just my little guy, is pretty open and spacious for dogs to move around, and I have fenced in my backyard just off the back door porch for even more run around fun. And now onto my prices, I had to do additions a certian way on here...As to plus a cat if I'm also coming to care for your dog...But I can always modify and give a discount if say you have many plus one cats in your home so it doesn't keep plus one'ing a fee...Or if you have wonderfully easy small dogs, I would not keep plus one'ing for those and would find a nice set fee, and especially if my little guy could also come enjoy them, or they could come spend the time with us...It's the large ones that can be more of a handful and take a bit more doing often times, that I have to have it set that way for. And I did just recently up my prices some as I've noticed that Rover charges per night and I am not loving that, I always on my own charge per day, so I up'd my prices some to reflect that. But have noticed that I am still under many, esp when it comes to multiple pets, and so that is good. So you can always send me a msg and we can discuss any and all options. I can often work staying elsewhere into my routine, even if many miles away...And I put a certain radius, which is more so for popins...But I have stayed in homes miles and miles away, out of state even, just ask if it's doable, it very well may be! But for pop ins and walks, I would prefer to travel within 10 miles or so from my home only. So I did just update this for a 45 miles out, but obviously I cannot be doing a pop in or daily walk so far away. I care for pets in my home or their home the same way I care for my pet in his home...With the added, well, additions that your pet may need. My home is often more foolproof safe...Such as I have an indoor fenced area around my front door...And I do sometimes bring something similar with me to others homes...I prefer to be (overly) safe than sorry.

Sitter Profile Image: TJ R.
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TJ R.
$36
total per walk
5.0 out of 5 stars
• 15 reviews
8 repeat clients
3 years of experience
Lawrence, MA, 01843

About: I’ve had furries since I was 4, dogs, cats, fishes! I believe all dogs and cats deserve to be treated with love compassion and attention no matter the size, breed, or species. I will love your pet like it’s mine and make them feel as comfortable as possible so you and your furry can have calm, fun and comfortable getaway! I work a part-time job so I’ll have plenty of time for the weekend all day long and doggy care/drop in visits/house sittings after 2pm I am available to take care of your furry at your home and provide them with the best care as well as attention and exercise!

Sitter Profile Image: Emily H.
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Emily H.
$55
total per walk
5.0 out of 5 stars
• 1 review
15 years of experience
Windham, NH, 03087

About: I personally have 2 dogs, the oldest is 15 years old this year and still healthy! I’m highly communicative, detail-oriented, and genuinely treat every dog like my own. I pay close attention to routines, energy levels, and comfort, and I always keep owners updated with photos and notes so you never have to wonder how your dog is doing. I’m currently working on app development for my own business, which gives me a very flexible schedule. This allows me to plan my days around pet care and be available whenever your pet needs attention, walks, or check-ins. I treat every pet like my own. I stick to their normal routine for feeding, walks, playtime, and rest so they feel safe and comfortable. I’m attentive to their behavior and needs, keep spaces clean and secure, and always keep owners updated with photos and messages.

Sitter Profile Image: Confesora B.
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Confesora B.
$78
total per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Whitinsville, MA, 01588

About: Hi my name is Connie short for Confesora! I love animals because they’re always there for us, they are highly misunderstood and much smarter and deserving of this life than Most humans believe! They deserve the best care even our little "not so easy" ones! If you have a not so easy one let me know ahead of time please!! Immediately inform me if your pets cannot control their bladder or rectum thank you. I have been working and volunteering in pet care And Grooming for 20 years! I am getting back into rover after two years away because A lot of life changes like becoming a cleaning company business owner happened! Regardless of whether they have fur or scales I treat my pets, and other’s pets as family members who need just as much love and emotional care as they do physical! I am also licensed and insured! We have a few dog parks available for play days! ! As a Furbaby owner you need someone who will treat your Babies as if they are their own family and that is one of the most important things people need! I have plenty of time to play with your pups and kitties!! I'm available for boarding on weekends and days of the week within limits! We have a fun friendly Cat Named Beau and an Old man named Ollie and a new young man named Rocky! Keeping your pets happy and satisfied and full of play time!

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The median cost per walk for dog walking in Winchendon is $25

Dog parents share their Rover experiences - Winchendon

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5.0 out of 5 stars

Jorden is always reliable, and has finally been accepted by my cat, who accepts no one! This is a true testament to Jorden's connection with animals!

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Chris A.
Dog Walking
5.0 out of 5 stars

Jorden is great with our dog Winston. Jordaen really takes the time to work with Winston on things he is still learning and Jorden let's us know Winston's growth. I would recommend Jorden. ☺️🐶

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Amy P.
Dog Walking
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How to book dog walking

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Popular requests for dog walking - Winchendon

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Sitters in Winchendon average 4
repeat dog walking clients

FAQs for Dog Walking - Winchendon

Frequently asked questions about Rover

The average cost of Dog Walking in Winchendon is $16 per walk as of October 2026. Most bookings cost between $16 and $42 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,132 sitters on Rover offering Dog Walking across Winchendon. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winchendon. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Winchendon after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .

Yes, you can find walkers who have experience with handling special pet needs in Winchendon. On Rover:

  • 89% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .

walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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