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%.
“Amanda was amazing with our two cats! She dropped in to check on them, feed them, clean the box, and give one of our cats medicine. She always stayed to play with them and she went above and beyond to clean up after them. They loved having her around!”
“Devon has been great! She's gone out of her way to work with us and our dog, between coming out multiple times for meet and greets and different scenarios, and just overall making sure he's comfortable with her. I would highly recommend Devon and am so happy we found her.”
“Absolutely thrilled with the quality of service. I received pictures and updates. My cats were well cared for, and it made being away much more comfortable. I would absolutely recommend.Amanda.”
“Super appreciate the last minute accommodation while we had to step out for a long day, as well as the pics and card update to know how our baby did while Jorden was with him!!”
“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!”
About: Hello my name is Jackson, My main focus & goal is to provide the best possible care and/or training for your dog, I Have experience working with Extra Large/High drive, working dog breeds. I currently own a 3 year old Male South African Mastiff (Boerboel) named Ivar weighing in at 180 Lbs, who I have spent countless hours of obedience training with, as well as socialization. I have owned & raised Ivar since he was an 8 week old puppy, giving me experience with juvenile puppy’s as well. Ivar recently underwent two surgical operations for torn CCL’s (Cranial Cruciate Ligament), with long recovery processes consisting of large amounts of Physical Therapy, specific exercises, walking, Running, and Swimming. I worked one on one with Ivar for many months Making him stronger and healthier than before. Thus giving me experience caring for dogs recovering from injuries/surgeries as well. I grew up, & lived in the New England region (New Hampshire specifically) the entirety of my life. I grew up on local and family owned farms, working with Cows, Draft Horse Teams, Sheep, & many more animals. I also have experience working with teams of Border Collies for sheep herding, as well as livestock guardian breeds (Shepherds, Mastiffs, Ect.) You can feel %100 comfortable knowing your furry family member is safe, well taken care of, as well as being fed & watered, & getting plenty of exercise & play time/interaction for healthy brain stimulation, & life longevity. As a Large Dog breed owner, I understand the fundamentals of patience, consistency, & devotion that comes with owning & training these amazing dogs, and I love every second of interaction with each dog I meet. If you have any questions, please feel free to reach out, & I will happily answer!! I am available in the morning 6 A.M.- 2 P.M. as well as any time during the weekends, please reach out any time, and I’ll be happy to make plans. Proper Care for your Pet is the upmost importance to me, I will treat your pet with respect and kindness. I can spend as much time needed for walks, playing & interaction, physical therapy, exercise, & any specific care requests you may have. Your pets well being, & needs will be met fully. & I will provide proper communication & updates of your pet so you can feel comfortable knowing your family member is ok and well taken care of.
“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.”
“Leo has been cared for by Danielle twice now and she has gone above and beyond !!! She had gotten him food the first time I went away on short notice. This time she was willing to go check on him when our flight got delayed !!! Honestly does a great job and I will keep her on the top of my list in the future.”
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.
“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 have spent my entire life around animals so caring for them has always come naturally to me. I grew up in a household with over 40 animals, including dogs, cats, and exotic pets. I have spent years working in a small locally owned pet store in my home town taking care of exotics, before moving into kennel work at a vet’s office. I have experience in giving medications to dogs and cats in different methods, and monitoring their health afterwards. My primary role was offering our boarding pets the comfort of a home away from home. I’m a reptile dad every day, taking care of my own snake and bearded dragon babies. I’m currently home every day with time and love to give to other pets and their people who need an extra hand. I have a big room with a comfy bed that they can lay on in a nice couch that we can sit and watch shows on. I also have a fenced in yard outback that I can take them in to play, but I have a spacious cemetery up and across the street that is great for leash walks as well. I also have various toys and litter boxes as well.
“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 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’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: 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!
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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Winchendon
Select a filter and find qualifying sitters offering pet sitting.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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