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!”
“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’ve always enjoyed being around animals and I know how important it is to have someone you can trust with your pet. I’m patient, responsible, and I’ll make sure your pet gets plenty of attention and feels comfortable while you’re away. I’m comfortable with both dogs and cats, whether they’re energetic and love to play or just want some company and attention. I’m also happy to help with walks, feeding, playtime, and keeping up with their normal routine. I’ll treat your pet like they’re my own and make sure they’re safe, happy, and well taken care of. I have an early routine. I would wake up early and feed the pups or cats. I would take them out for walks through out the day and feed dinner in the evening I have a very calm home, i do have a cat and dog, they are both sweet and loving and would love a new friend.
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! 😂
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.
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
About: Hi! I’m JuJu, a happy-go-lucky animal lover who’s had pets my entire life. I grew up caring for dogs, cats, birds, and even farm animals — I never had to ask Santa for a pony because I actually had one! Being around animals has always come naturally to me, and I treat every pet with the same love and attention I give my own. Whether your pet needs playtime, snuggles, slow-and-steady care, or a fun walking buddy, I’m here to make sure they feel safe, comfortable, and adored while you’re away. I’m reliable, patient, and great at following routines. I’m also happy to send updates and photos so you always know how your furry family member is doing. I can’t wait to meet your pets and make them feel right at home! I’m a mom getting settled here in Massachusetts, and I currently have a very flexible schedule. I’m able to fit drop-ins and walks around my other duties, and I’m happy to help even on holidays. If you need reliable care at a specific time, just let me know—chances are I can make it work! I always make sure your pet feels safe, relaxed, and cared for while staying in their own home. I follow your routines closely so everything feels familiar and comfortable for them. They’ll have fresh water, a clean space, and plenty of attention. I’m very mindful of safety—whether I’m giving them playtime, keeping them company, or taking them for a walk. I also send photos and updates so you always know how your pet is doing. Your pet’s comfort and happiness truly matter to me.
“Zachary helped take care of my kitty Zeus while I was away for an extended period of time. Zachary sent me updates with each visit to keep my mind at ease. He is a dependable sitter and I recommend him for your pet care needs.”
“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 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.
“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!”
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.
“Thank you Haley! My first time with her as we traveled for a bike event today. Great service and quick response to request! Next time in area and need pet sitting will reach out. Stay cool super hot here today”
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!
“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.”
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. I'm available for drop in visits and dog walking. I do not yet 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.
“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: 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 Drop-In Visits - 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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