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 67 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%.
“Jorden was amazing with our large lad for this drop in! This was our first time leaving Whiskey for an extended time and I think Jorden was the perfect person to check in on him. Will definitely be rebooking in the future!”
“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!”
“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.”
“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.”
“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!”
“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!”
“Colin is always amazing with our crazy boy! He is reliable and always works with Remi on treats and walks as well as feeding him lunch. Colin has helped us out on a couple last minute changes too and that is so nice to have someone reliable and who loves our boy like we do! Will continue to have Colin as our go to person on Rover for our Remi!”
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: 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.
About: I’ve had dogs all my life and my philosophy is “the bigger, the better!” I have experience caring for big, medium and small dogs, cats, turtles, and other pets. And I give every animal I meet a personalized nickname! I’m currently working 40 hours a week. I leave around 7:30AM for work and get back around 4PM. With my current schedule, I could do weekend pet care or pet care for those who don’t need as much attention during the day (ie. don’t need to go outside to use the bathroom). To keep your pets safe in your home, I will follow all instructions regarding feeding, medication and routines to the letter! I also have a dog at my family home and a cat in my own apartment, so I am very vigilant about keeping doors closed and locked so no pets escape. I am also down to send update photos and messages if wanted!!
About: Having spent my entire around dogs and now a proud dog mom to a 3 year old Australian Shepherd named Willow, I am well acquainted with the responsibility of pet ownership. I can offer security for families and dog parents when traveling away from home. I offer home boarding with a large back yard for play and doggy adventures. As an active person who loves being outside with an active dog partner I provide exercise for your doggy friend while your away. I can supplement daily cares of caring for a pet including basic grooming and medication suspension if necessary. Not afraid of large breed dogs or those with anxiety I welcome dogs of all sizes and temperaments into my life. When we travel we should travel with confidence knowing our furry friends are well taken care of, let me help you travel with confidence.
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!
“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 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
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.
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 September 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 September 2026, there are 1,201 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:
- 90% 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.
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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