Pet Sitting Winchendon
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 75 pet parents in Winchendon have booked pet sitting
Winchendon, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Devon was great visiting our home with our nervous pups that are never separated from their humans. The pictures and updates were extremely reassuring and gave us peace of mind while away for the weekend! We will absolutely reach out again,”
“We decided at the last minute to go away for the weekend and had no dog sitter. Emily was available that day to meet our pups and then take care of them for the weekend! We received pictures and updates from every visit and came home to happy healthy pets. Thanks Emily!”
“Danielle was great! I would highly recommend. My boarding place fell through last minute due to a scheduling mix up. I was able to book Danielle only a few days in advance. My dog, Nala, was so happy when I got home. You can tell she had lots of care and love! I always appreciate when people make connections with my animals. It makes the dress of leaving animals during travel a bit easier.”
“Taylor was great with my 2 cats! I have one very shy cat who typically hides under my bed whenever anyone unfamiliar is here but he came out to say hello to her! Would very much recommend!”
“Emily was wonderful! She came over for a meet and greet before taking care of our three cats. I appreciated her taking the time to do that. She was extremely thorough and very communicative which I also appreciate it. She took great care of the cats and my house! She really went above and beyond. I appreciate her and definitely recommend hiring her.”
“Margaret & Dawson were great and took care of our pets like they were their own. Very trustworthy, dependable and communicative. They sent us pictures and videos of the pets with each visit. We recommend booking with them and we will book with them again in the future!”
“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’ve always loved animals and have spent many years helping friends and family take care of their pets. It’s something that brings me a lot of joy. Over the years, I’ve looked after all kinds of pets — from energetic pit bulls and bulldogs to small dogs like Shih Tzus and even cats. Sometimes I’ve stayed in people’s homes for a week or two, and other times I’ve just stopped by for walks or check-ins. I’ve also welcomed pets into my own home when friends needed someone they could trust. I have a calm, friendly personality and get along well with animals, even if we’re meeting for the first time. I’m always careful to notice when a pet might be nervous or needs some space, and I do my best to make sure they feel safe, happy, and cared for. My schedule is very flexible since I work a per diem job and can choose when to take shifts. This gives me plenty of time for pet sitting, walks, or overnight stays. I’m usually available on short notice, too. The only thing I plan ahead for is care for my own cat while I’m away, but that’s easy for me to arrange — so it won’t affect my availability or reliability. When I’m caring for pets in their own home, I do my best to keep their routine as normal and comfortable as possible — feeding, walks, playtime, and cuddles just the way they’re used to. I make sure they feel safe and cared for while their family is away. If a pet stays in my home, I treat them like one of my own. I create a calm, cozy environment with plenty of love, attention, and playtime. I also make sure to follow any specific instructions from the owner so each pet’s needs are met. I’m gentle, patient, and understanding of different personalities — whether a pet is shy and needs space or energetic and ready to play.
About: I’m a very responsible and loving pet owner. Have rescued many pets and now have found myself with some free time and would love to help new pets and people! With notice, I am completely free on Wednesdays, Thursdays, Saturdays & Sundays. (Monday, Tuesday & Friday I can be available for a few hours in the am) I have a fenced in yard with plenty of space to play and a kiddie pool to cool off in! I have three very friendly doggos myself but plenty of space so they can be kept separate if you desire.
“Colin is wonderful! Colin is determined to stick with it and meet my slow to warm up girls where they're at. I got home a couple hours ago to find two intact and wholly themselves dogs. They're now definitely ok with Colin coming into their world. I'm thrilled both that they're definitely making friends with Madeline and that Khloe has started coming out. She does exist! Thank you!”
“Kellee did a fantastic job with our kitties. Followed the feeding instructions. They can be difficult since one of our kitties is 19. She went over and above and brought in our mail. We will hire her again.”
About: I’ve taken care of cats, dogs, snakes, chinchillas, quails, pigs, lizards, Guinea pigs, and bunnies. I am willing to learn how to take care of any animal and have given medicine/received special requests previously I work 4-8 hours a day and one of my jobs is a work from home job. My timing can can be flexible unless I am lifeguarding. I do not offer boarding. I do have pets of my own and would take care of other peoples’ animals according to the owner’s and their vets’ wishes and judgement
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.
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 pet sitting in Winchendon is $25
Pet 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!
Jorden was so patient and wonderful with our shy and spicy cat Lola this week - going above and beyond to make sure her litter box area was tidy when we got back and communicating with us at the same time every day while we were away for a week long trip. We were able to relax knowing Lola was in good hands with someone so responsible and caring!! We highly recommend Jorden!
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
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 near you
Select a filter and find qualifying Winchendon sitters!Sitters in Winchendon average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winchendon
Frequently asked questions about Rover
The average cost for Pet 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 Pet 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 Pet Sitting. For more information on service fees, click here .
As of July 2026, there are 1,282 sitters on Rover offering Pet 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.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
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.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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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