Dog Sitting Winchendon
Book a Winchendon dog sitter to watch your dog in your sitter’s home or yours.
Over 48 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%.
“Amie was a rockstar! She was very thorough and asked appropriate questions to ensure the best possible care for my cat. She is knowledgeable, has excellent communication, and provided detailed updates. She was incredibly kind and patient with my anxious kitty, and I am so grateful to her!”
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: My name is Molly, I live in Gardner MA, I work from home so my schedule is flexible. I also have weekends off. I love cats and dogs!! I have experience in walking dogs, doing over nights at homes, and doing drop in visits with cats and dogs. I could help with any other animals you may have also. I have 2 cats of my own and a almost 2 year old dog. I have helped a lot of people that I know personally with their animals And I am looking to branch out! I can help with older animals or new kittens/puppies. Please feel free to reach out to me I would love to help! I work from home so I have time to attend to your animals needs. I get off around normal business hours so I can attend to them any time after work also. I have a lead in my yard- my dog loves playing with other dogs. I have a crate in home already. I can also separate my dog if you prefer!
“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!”
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.
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
“Nadine did an amazing job with our cat. Lots of playtime and pets when she stopped by for an evening drop-in. She kindly sent videos and pictures too! We hope to use Nadine again in the future!”
“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: 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! 😂
“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 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: 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.
“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!”
“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.”
“We live in Hardwick.Mandy took excellent care of both of my cats. One of my cats has a chronic illness which required that Mandy give him an injection. She has previous vet tech experience so that was no problem at all. Mandy sent me an update with pictures of both cats. She even came to our house before our trip to meet the cats. We would highly recommend her.”
“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: I’m the go-to person for anyone needing pet care on short notice. I have a big yard and I live on a dead end street so it’s a very safe place with lots of mobility for your pet! I’ve learned to be an excellent care taker since I was young and I enjoy doing so now as a result. I’m a nanny so being patient and caring comes naturally. Lmk if you have any questions/ concerns. :) I can accommodate to anyone’s schedule as they may need. I work as needed (on call) so accommodating won’t be a problem. I’d prefer a 2-3 day notice but I can always make an exception if I have the time. I have a big open yard and long leashes to let them roam around as they’d like without feeling restricted. I like to spend time outside so that will be majority of the time we spend together if you hire me! I can accommodate to however you like your pet to be cared for. I’m all ears for instructions/ schedules.
The median cost per visit for dog sitting in Winchendon is $25
Dog parents share their Rover experiences - Winchendon
Jorden was great asset to us by agreeing to drop in on our dogs at the very last minute of a holiday weekend. Our dogs are mixed rescues and very odd - but Jorden showed up and even stayed a bit longer than requested to see if the dogs would potty, even though they decided not to- Jorden tried and that speaks volumes to us. We were already comfortable with Jorden around our pets and home from all the previous feedback on Rover. Jorden gets accurate reviews and with our experience would say never hesitate to book Jorden as your sitter.
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 Dog Sitting - Winchendon
Frequently asked questions about Rover
The average cost for Dog 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 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 September 2026, there are 1,150 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:
- 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.
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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