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%.
“Emily was amazing with Pepper, my shy hound. Emily showed up promptly for each visit and was very thorough. Even her pre-visit questions were thorough. She is very caring and kept me very informed. I highly recommend Emily.”
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!
“Zachary was easy to work with and also very friendly to our dog. He was on time for the check ins, and sent along pictures/updates with how our boy was doing. We highly recommend Zachary, and we will certainly utilize his services again if the need arises!”
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! 😂
“Haley once again did an amazing job taking care of our two cats while we were gone for over a week. They were immediately comfortable with her on the first visit. She sends thorough updates and photos every visit showing them playing and interacting with her. I highly recommend her services. She's very reliable and communicative, and is a great fit even for skittish kitties. It was such a relief to know that she was checking in on our cats while we were gone!”
“Misty has had excellent communication from day 1. My three pups took to her immediately which made us feel at ease. She was able to give us a hand with short notice when we had some last minute changes to our work hours. We received some adorable photos of our babies when she came by to let them out. If you’re looking for someone who loves dogs, can work with a flexible schedule and has excellent communication then Misty is your person.”
About: I grew up with a dog by my side always. I have had experience working at a doggy daycare and doing check ins on dogs throughout the day. I love dogs of all kinds and will treat them as if they are my own I have always enjoyed working with animals especially dogs, and would love to include this in my daily routine. I can do mornings and afternoons! I always treat every dog as if they are my own. I care deeply for animals, and will take good care of yours when you can’t!
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. 🐾💖
“Roxanne came and checked in on my cat everyday for 2 weeks. I got pictures and videos and felt so happy knowing my baby was being well taken care of. Usually my cat has separation anxiety but when I came back she seemed so happy and healthy!”
About: Hi, I am a huge dog lover. Your dog will be safe with me. I’m a kind and trustworthy person. I love to help and I hope to meet your doggo! I am in college so this means I am available throughout the day. Send me a message and I’ll gbe sure to make you and your pup a priority I am working part time. I will have plenty of time to visit and be with your dog! I am flexible and will be working from home. I have a friendly dog named Piper, we live on a dead end road and have plenty of room to run! I am ready to love and take care of your dog!
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
“Sarah-Jane is a respectful and responsible sitter. I had an impromptu engagement and she was very helpful at such short notice. She took the time to meet YaYa first before the sitting and to get a little familiar with the routine. My dog YaYa loves her and looks forward to the next time Sarah-Jane can watch her. Sarah-Jane also left me a very nice thank you card which was very unexpected.”
“This is the second time that I used Amad to care for my cats, he has been great, will stay and play with them, easy to reach and will quickly respond . Overall we highly recommended .”
“Tessa is so wonderful! Our dogs did extremely well with her for her 1st time meeting them. We appreciated her patience with the boys, and that she came from the distance that she did to meet and get to know them.”
About: I love animals and have been around them as long as I can remember. I have extensive experience with dogs and cats, from birth to their last breath. I believe in positive reinforcement training. I am very loving and treat all animals with respect but can be strict when required for safety. With me your babies will feel like they are at home away from home. I work from home and have a very flexible schedule. I am available almost always and your fur babies will have lots of love and company. I have a large grassy yard, and I live near a pond and multiple trails. I also have a Chihuahua mix girl, who is very friendly and loves making new friends.
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?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
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
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog sitting - Winchendon
Select a filter and find qualifying sitters offering dog sitting.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 August 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 August 2026, there are 1,177 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
- 92% 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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