Dog Sitting Winchendon
Book a Winchendon dog sitter to watch your dog in your sitter’s home or yours.
Over 51 pet parents in Winchendon have booked dog sitting
Winchendon, Find top rated dog sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: Lifelong dog owner, active dog walker, and aspiring dog trainer. I have experience with dogs of all ages, temperaments, and energy levels and am passionate about canine behavior and enrichment. With over 10 years of animal welfare volunteering and experience caring for horses and farm animals, I understand the importance of patience, consistency, and building trust with animals. Every walk is an opportunity to provide exercise, mental stimulation, and positive experiences for your dog. Pet care fits naturally into my daily routine. I am active and enjoy spending time outdoors, so regular walks are already a part of my day. I have a flexible schedule and can provide dependable walks, drop-in visits, feeding, playtime, and companionship. I understand that consistency is important for dogs, and I strive to be reliable, punctual, and communicative with every client. Your pet’s safety and well-being are always my top priorities. As a lifelong dog owner with experience caring for cats, horses, and farm animals, I understand the importance of reading animal body language and respecting each pet’s individual needs. I always follow owner instructions carefully, use secure leash handling practices, and provide plenty of positive attention during walks and visits. I’m currently working toward becoming a dog trainer, which has strengthened my understanding of canine behavior and safe handling techniques. You can trust that your pet will be treated with patience, kindness, and the same level of care I would give my own animals.
“Liz handled Daisy exceptionally well, even cleaning up after her when she had an accident. We can now leave Daisy with Liz next time, confident that she's in good hands. Despite Daisy not being well-socialized, Liz managed her wonderfully.”
About: I have had dogs my entire life and currently own three. I have experience with a wide variety of breeds and have cared for many dogs beyond my own. I am currently a veterinary student at Midwestern University and have a strong passion for animal care. I am confident handling multiple dogs at once and lead an active lifestyle, ensuring pets receive plenty of exercise, attention, and high quality care. I am committed to going above and beyond to meet each pet’s individual needs. Pets have been a big part of my life since I was born and I am taking the passion I have for animal care into my career. I am currently a vet student at Midwestern. Your pet will feel at home and comfortable. I will make sure their schedule stays the same and they are fed and walked at the time given.
About: Pet Care Experience: I’ve been caring for animals my whole life! 🐾 From my time in 4H, where I competed with my own animals, to looking after pets of all kinds, I bring experience, dedication, and a deep love for animals. Whether it’s caring for energetic puppies, providing companionship for senior dogs, or making sure your pet gets the right amount of playtime and love, I’m here for it! ❤️🐶 I specialize in: ✔️ Puppy care & basic training 🍼🐕 ✔️ Senior pet support 🦴🐾 ✔️ Administering medications (oral & topical) 💊 ✔️ Walks, playtime & belly rubs! 🏃♀️🎾 Your pet will be treated like family while you’re away! 🏡💖 Schedule: 🐾 Pet care is my #1 priority! 🐾 I have a flexible schedule since I’m currently in school, which allows me to accommodate morning, afternoon, and evening visits. Whether your pet needs a quick potty break, a midday walk, or overnight care, I can work with your schedule! 📅🐕 Safety, Trust & Environment: I believe pets are happiest in their familiar environment, which is why all care is provided in your home. 🏡💙 Here’s what I offer: 🐾 Regular check-ins for food, water & potty breaks 🐾 Daily walks tailored to your pet’s needs 🦮🚶♀️ 🐾 Playtime to keep tails wagging 🎾🐕 🐾 Overnight stays for extra comfort & security 🌙🐾 I always ensure pets feel safe, loved, and comfortable while you’re away. 🐾💖
About: I have had dogs and cats, and also a horse for most of my life! My current dog is a 10 year old rescue from Tennessee, and he’s the love of my life. I’ve worked very hard with a trainer with my pup, so I have some experience there. I volunteered at the humane society and ASPCA for many years off and on, and I also fostered dogs throughout college. Safe to say I have plenty of hands on experience with all sorts of pets :). I am working full time, but I have a somewhat flexible schedule! I have plenty of time throughout the day to spend some time with whatever pet needs the attention! In my home, my dog is pretty spoiled :). He is my main priority, as it is just him and myself, and it’s been that way for years! As far as other people’s pets in their home, I will follow any instructions in detail that are provided, but above all I will make sure the pet is happy and healthy and comfortable!
About: I’ve been working for a company based out of Sudbury Ma for 5 years and I’m just looking for extra work :) I’ve worked with dogs of all sizes, ages etc. I have worked with dogs of all temperaments as well. Would love to get to know your pet :) I work full time walking/ pet sitting for a company Monday - Friday and weekends for sitting. I’m looking to expand to some new clients! I could even bring your dog with me for the day on walks with other dogs if I’m sitting them and they would be up for it I can stay in someone’s home or have someone’s dog/ dogs stay in my home if they are friendly with other dogs as I do have my own dog
About: I grew up with labs, mastiffs, collies, and shepherds. I treat my dogs better than my family at times! Play, comfort, and love are staples. I work full-time during the week, but am home most weekends with my 11 month old socialized lab. My dog receives daily exercise and active play and yours will too! I will ensure your dog’s safety and your peace of mind by taking them out on leash for walks and bathroom breaks. I value active play time and also work in rest times.
About: Hello, my name is Melanie! I recently quit my job to focus on school and am looking to get back into pet care! I've grown up with a bunch of pets from dogs, and cats to more exotic animals like reptiles, ferrets, and birds. I've also worked at a pet store for 5 years, as well as my fair share of family and friends pet sitter. I currently go to school full time, and spend the rest of the time studying with my pets! In our house we have a schedule and take turns when it comes to feedings, bathroom needs, and everything in between! Personally, I own one dog myself, Kira and she likes to spend all of her time outdoors, and is a snuggle bug. Kira also eats a very specific diet as she has allergies and takes supplements. I live in a house everyone is extremely welcoming to all pets and offers a vast fenced space for playing, although I prefer to not host, pets myself. I also have training experience and focus on positive reinforcement and leash training! I'm currently in school, so I'll have plenty of time to care for your pups. I'm available weekdays. Weekends are usually open. Mondays- Anytime Tuesdays- Before 10am and After 5pm Wednesdays- Before 1:30pm and After 5pm Thursdays- before 10am and After 2pm Fridays- Before 10am and After 5pm (This will change middle of May 2026) I'm very good at following instructions and asking for clarification if needed. I always use single ingredient treats that are usually allergy friendly (lamb liver). I pride myself on being safe and respectful to everyone!
“Can I give Amadie 10 stars??? We had recently lost one of our kitties and had a 10 day vacation scheduled plus we had moved so needed a pet sitter for our senior, very shy kitty. Amadie was the perfect fit! Our senior kitty warmed up to her and she actually let Amadie pet her a few times. This was a first for anyone besides me or my husband! The patience, love and care she showed to Luna was beyond anything we ever expected. She also was so caring for our home and reached out with questions. Amadie communicated with us daily, pictures and updates. We will definitely ask Amadie to care for Luna again.”
“I highly recommend Kayla G. My dogs are very spoiled and do not really like people who do not live in our house, but they love her. I have asked Kayla back a few times so I could go away on vacation and she was very communicative and took great care of them.”
About: I’ve always owned dogs and cats! Right now I have a male German shepherd! Previously I had a female German shepherd. I would love to help anyone who’s in need of care/play for their dog/s and or cat/s! I currently work 3, 12hr overnights. I will be available for mornings and later afternoons/evenings! Let me know what the needs are to take care of your pets! I will not be able to board at my house. I will only do drop in visits for care needs and let outside to do their business.
“This was my first time using a pet sitting service so I was pretty nervous. Bradleigh is super friendly and outgoing and made this experience stress free! I highly recommend Bradleigh and wouldn't hesitate to choose her again in the future.”
About: I used to babysit for my friends, family membersand & neighbors. As well as I've had many pets of my own; cats, dogs guinea pigs, hamsters, you name it. I'm very good at handling bigger dogs. I'm very flexible when it comes to time and will work around your schedule. I'm currently home from college for spring break and my time is very open for both weekends and weekdays. My working hours start at 7am and go till 11pm. (But I can fluctuate with your schedule) I have a fenced backyard. And one very friendly small/medium dog, he's a little shy, but he gets along with everyone. I believe that our pet should be treated like family members. Walks, treats, attention and lots of love.
About: I have had a passion for taking care of animals since a young age. I have experience with all types of animals. I worked as a doggy daycare attendant and a veterinary assistant. I currently work at an animal shelter. I'm currently working 2 part time jobs. Wednesdays, Saturdays and Sundays availability with the possibility of Mondays. I'm available for dog walking, trips to the dog park and pet sitting. We do have a backyard which is not fenced in and a porch that I usually block off to let my dogs get outside for some fresh air.
About: I’ve owned pets since my daughter was young and brought her first kitten home. I’ve been helping her to walk dogs for a couple years now. I’m retired so my schedule is fairly open. It gets me walking and outside, two things I enjoy. It helps my health and makes me feel good. Happy to walk your dog! Cannot have pets stay at my house as I have a kitty cat of my own. His name is Toby and he’s a real pain in the butt! 😂
“Nadine did an amazing job with our cat. Lots of playtime and pets when she stopped by for an evening drop-in. She kindly sent videos and pictures too! We hope to use Nadine again in the future!”
About: I love dogs. I have a rescue her name is Snickers and shes 7 months old. I've had dogs all my life. How anyone can hurt man's best friend is beyond me. She is like my child and makes me smile, keeps me company and I dont know what I would do without her. I love her with all my heart and wouldnt trade her for the world. I would treat anyone's dog like I would my own. They are all special in their own way. I would be honored to take care of your dog, I look forward to meeting you very soon. Thank you, Robin K I work full time at home and I'm able to walk my dog and take her out anytime! I'm available all day. My Snickers would love a play mate. I dont have crate but if yours needs one you'll have to bring it. I'm very diligent in taking my pup out all day long.
About: I’ve taking care of different kinds of dogs even puppies that family and friends had me help it with a few years ago till now. so I am available to help during the week and some weekends as well I will start be available for weekends in November it. Ask me any questions you may have. I am here Hi! I’m a dependable and loving pet sitter who enjoys spending time with animals of all personalities. I’m patient, attentive, and committed to keeping your pet safe, happy, and well cared for. You can trust me to treat your pet like family.
The median cost per visit for dog sitting in Winchendon is $25
Dog parents share their Rover experiences - Winchendon
Devon is awesome!! She came to spend some time with our 5 month old puppy while he was home for the day. She was very capable of handling his puppy behavior, she came on time & played with him until he was exhausted. We would definitely hire Devon again and appreciate her taking such great care of our baby!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
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Select a filter and find qualifying Winchendon sitters!Sitters in Winchendon average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Winchendon
Frequently asked questions about Rover
The average cost for Dog Sitting in Winchendon on Rover is $27.75 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 1,228 sitters on Rover offering Dog Sitting across Winchendon. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchendon stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winchendon choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter 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 Rover's Trust & Safety page .
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 Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winchendon with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winchendon. On Rover:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 94% 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.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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