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 69 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%.
“Emily did an awesome job caring for our two kitties. She was on time each time and they were well cared for. We will definitely reach out to her again when we have another kitty sitting need!”
“Emily did a wonderful job watching our cat! We had a meet and greet a couple of days before our trip which was very helpful, and Emily sent photos and a lovely note every day. She was also extremely flexible and accommodating when we had to deal with an unexpected change of plans mid-trip, and made the schedule change as painless as possible. We would absolutely book Emily again!”
About: Animals are my passion. I've cared for dogs, cats and exotic animals my entire life with a background in Veterinary Medicine and years of education in training/ body language, early socialization and enrichment work. I treat, care for and love all animals as they are my own. I can provided care for pets of all ages with any special needs, medications, grooming needs and more. Reliable, flexible, and trustworthy. Flexible availability! Weekdays, nights and weekends for your pet needs. Available multiple or one drop in(s) for feedings, walks, medications, playtime or general 1:1 time. Can also be available to stay the day. Although I do not board pets at my household or offer overnight stays. I am available for walks and drop in visits ranging from 1-6hrs anytime of the day. I am very respectful of others space and am always very cautious and Intune with your pets well- being.
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, as well as shelter experience. I'm available for drop in visits and dog walking. I do not have a set schedule at work yet so I will have different availability every week. 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: Owned and taken care of dogs and cats since I was young. Can’t remember a time without having pets! Currently own two crazy pups and two pretty kitties, and can’t wait to meet yours. Have experience with senior dogs, puppies, and everything in between. I am a full time firefighter/EMT, so I only work two 24hr shifts a week, and the rest of the time I get to play with yours, and my own animals! Love to hike or be outdoors with as many pets as possible! If they’re happy, I’m happy! I will follow all rules set for your pet, and be sure to keep their safety at the top of the list! As a pet owner, I can’t imagine something happening to my own animals, and I would never want to let anything happen to yours!
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'm a lifelong dog and cat owner who treats every animal like family. I build strong bonds with dogs through communication, patience, and positive reinforcement. I enjoy basic training, teaching tricks, playing, walks, and giving dogs the attention and companionship they deserve. I want every pet in my care to feel safe, comfortable, and loved. I'm looking for side work taking care of people's pets along side my loveable Labrador. I'm available for walks, car rides, pet sitting and pet check-ins. I care for pets with patience, attention, and genuine affection. I follow each pet’s routine and the owner’s instructions closely, including feeding, medications, walks, playtime, and any special needs. I take time to understand each pet’s personality and comfort level rather than treating every dog the same. I provide plenty of companionship, positive reinforcement, exercise, and mental stimulation while making sure they are safe and comfortable in their own home or mine. Most importantly, I want every pet to feel like part of the family while they’re in my care.
“My cats were well cared for while we were gone. Dee had good open communication with us while caring for our cats, she asked questions if something wasn't clear and was very honest with us about everything. Thank you Dee!”
About: early years, my family were training Morgans for the Kentucky Derby. It had been an exhilarating journey, one that beautifully intertwined skill, patience, and a profound bond with these majestic horses. Each horse is unique, deserving of personalized training that not only harnesses their incredible speed and agility but also fosters a deep connection between horse and trainer. As l've grown, my focus has shifted from merely training to cherishing those heartfelt connections, as they truly enrich my life. Alongside my passion for equine training, I find immense joy in the companionship of dogs and cats, nurturing their spirits It’s all I do - besides writing. I chose to step Away from The chaos of the world to care for my own well being by taking care of animals. With respect, kindness and love as I would expect in my own home and with my own pets. Pets bring joy and peace to my life.
“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.”
“I would recommend Elizabeth for all your dog watching and walking needs. She was very professional and my dogs were friendly with her. She has a lot of experience with dogs. Cheers, Kevin G”
About: Who doesn’t love a dog?! They're innocent and give unconditional love. And they love my scratches and pets. Prefer animals over people for sure, honestly I’m searching for my new adventure, enjoying having an easy flexible life currently and enjoy being able to give owners peace of mind when away. I follow the owners preferences and take care of them as if they were my own. I give them all the attention and love I can.
“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.”
“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: I have worked in vet med for going into 3 years I have lots of expertise with anxious and aggressive dogs aswell as being able to administer medications. I have also worked at dog daycares and understand the fundamentals of dog behaviors. Since I am a vet med personnel I really enjoy being around pets where I can spend time with them outside of the vet office and more one on one happy visits. I care for my pets very accurately. I make sure every step is done for them and there is no missed points. I’m happy to do long walks with your pet and any tasks for them to improve their quality of care. I have my own cat in which I spend hours of my time with
“Dina and Jason did a great job with watching our cat over the Thanksgiving holiday! Very thorough updates and it was clear that our boy had a good time while in their care. That's saying something considering he's on the older side and can be picky about who's caring for him. Thanks again!”
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!
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 to book pet sitting
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 Pet Sitting - Winchendon
Frequently asked questions about Rover
The average cost of Pet Sitting in Winchendon is $28 per visit as of October 2026. Most bookings cost between $20 and $39 per visit. On Rover, sitters 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 1,186 sitters on Rover offering Pet Sitting across Winchendon. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 .
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.
Yes, you can find sitters who have experience with handling special pet needs in Winchendon. On Rover:
- 87% of sitters can help with special care needs
- 93% 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 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 sitter 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 sitter 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 sitter for longer stays or first-time bookings. Read our tips for your first .
sitters 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 sitter.
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