Pet Sitting in Winchendon
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winchendon pet sitters

“Devon was an excellent sitter for our cat Moose. She fed him and played with him while we were away for a week. Devon was responsible, quick to respond, sent photos of Moose everyday, and wrote about each visit. Good communication and clearly loves what she does! Cats don’t always warm up to people right away, but Moose did when they first met. Devon even came to meet us and Moose before booking which was very helpful! I will definitely be using Devon again!!”


“Danielle was great! She was easy to communicate with and provided thorough updates with plenty of pictures while we were away. This made me feel comfortable that our cats were in good hands and well taken care of. I’ll be reaching out again when needing a pet sitter. Thanks Danielle!”


“Katrina was the best with my dog and cat. She kept me updated every visit and they seem comfortable with her. She fed them and kept the space clean for them! I would definitely book her again.”


“Amanda came through for us last minute when we had a schedule change! She’s great with both our dogs and always shares updates on how the visit went. Having one anxious pup, we always appreciate hearing about their time together, and it’s been awesome to work with Amanda as our young rescue opens up and gets more confident. She’s also great at recognizing when our two dogs have different needs, and letting them do what’s best for them - today our young dog wanted to play outside and our senior dog wanted to snuggle on the couch after going potty because it’s cold and gross. Highly recommend working with Amanda!”


About: Proficient in providing dogs with stimulating and safe walks. Meticulous in following schedules with feeding. Comfortable and experienced in administering oral and topical medications. Knowledgable in basic dog first aid and safety protocols. As an owner of a 5 year old Golden Retriever since puppy age, and dog sitter, I have taken the responsibility of taking care of any dog! I strictly follow eating schedules and/or medication schedules. I pay as much attention as possible, as an owner of a golden this is a must! I make sure I leave a safe environment for my doggies. I attend to their needs whether it is to be by themselves, or get all the playing time they need!

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 care for dogs of all sizes and ages for 6+ years. I'm patient, loving, and experienced Wirth senior dogs, medications, and gentle outdoor routines. I'm currently work part-time, which gives me plenty of flexibility to care for pets, I'm available for boarding on weekends and during weekdays after 6 pm. Your pup will get plenty of attention, walks, and playtime. I have a fenced yard and one small dog who prefers her own space. To ensure safety, I separate visiting dogs when needed and always supervise interactions closely. I create a peaceful, clean environment where your pet will feel secure and cared for.

“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 have had a dog since I was born. My dog and I grew up together, learning together. Saying that I’ve had my fair share of experience being with pets. I have always had the responsibility to learn how to take care of them and their needs and we can’t forget having fun with toys and walks. Recently my dog sadly passed away and I would love nothing more being pets again. I currently work night shift during the week. So I’ll be available during the day after 7 am for playtime and walks and making sure they are fed and whatever they may need. I also have the weekends off Unfortunately I do not have a fenced in yard but I do have lots of grass for them to run around in and live in a quiet neighborhood perfect for walks. Since I’m used to having two dogs in the home, I can accommodate most specific needs.

“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 loved and been taking care of dogs for as long as I can remember. Dogs are my life and I hope to be able to share my experiences with dogs with others. I am certified in Veterinary Technician Assistance and am working on my dog training certification and will be working toward a career in canine behavior. I have experience with all kinds of dogs with all kinds of personalities. I can't wait to meet and help care for your fur babies. I am currently a stay at home wife and mother looking to work with dogs. I am familiar with the daily care of a variety of animals. I trust all dogs as if they were my own. As an avid dog lover they are my life and I strive to provide each dog with the proper care and love they deserve. I have some basic training in canine first aid and a basic knowledge of canine CPR.

About: I am a proud dog mom of 3 dogs and we use to have a cat. As you can imagine, I am a huge animal lover of all shapes and sizes! We have two pitbulls and a Chihuahua. Happy to do last minute drop ins to feed and love your pups if you are having a late day at work or weekends! Wednesdays, Fridays and weekends are the easiest days for me to care for your pets but I am flexible and can make anything work that you need. I will always care for your pup like it’s my own and make sure they are happy, safe, and loved. All dogs deserve that ❤️

About: I worked in an exotic vet hospital for 7 years which is also a wildlife rehab facility. Prior to that I have raised and cared for animals of all species of my own my whole life. Whether fury, feather, scales, or more I love just about every living being & critter. I will care for your pets like they were my own. *Making a note that poisonous/venomous or illegal animals are not acceptable or allowed. I have experience with reptiles like geckos, bearded dragons like my own, iguanas, turtles, birds of all shapes, color, and sizes, some farm animals, ferrets, guinea pigs, hamsters, rabbits, and things of the like. Animals that are venomous or harmful are excluded.* I care for and hang out with my fur babies, but there's plenty of room and time for more friendly faces. I work hard so my pets can have a good life. 😂 I frequently walk my dogs and can take yours around the neighborhood as well, lots of dog toys, pats and belly rubs, and can crate your pup if needed. Im also willing to help with some trainings and house breaking if requested.

About: I have been dog sitting and housesitting for the past five years. I have a lot of experience in senior animals as well as animals with special needs. I am very reliable, respectful, and understanding when it comes to housesitting and pet sitting. I have a lot of experience and will always try to accommodate you and your animals the best that I possibly can! I am currently looking for colleges as a graduate of a dual enrollment program! I graduated in 2022 with a high school diploma along with an associate’s degree in undecided! I have a total open schedule when it comes to pet sitting! I will always make it my number one priority to make sure your animals feel safe and comfortable with me. Being away from owners can be stressful enough, that’s why I always make sure they are happy and comfortable while missing you! Any rules you ask of me to follow, will be followed! I am very understanding and very open to just about anything. :)
Loving pet sitters in your neighborhood
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Aurore L.

“Awww, I think Goose likes you! Lol”


Devon P.Star Sitter

“Devon was an excellent sitter for our cat Moose. She fed him and played with him while we were away for a week. Devon was responsible, quick to respond, sent photos of Moose everyday, and wrote about each visit. Good communication and clearly loves what she does! Cats don’t always warm up to people right away, but Moose did when they first met. Devon even came to meet us and Moose before booking which was very helpful! I will definitely be using Devon again!!”


Danielle K.

“Danielle was great! She was easy to communicate with and provided thorough updates with plenty of pictures while we were away. This made me feel comfortable that our cats were in good hands and well taken care of. I’ll be reaching out again when needing a pet sitter. Thanks Danielle!”


Jorden A.Star Sitter

“Jorden did a great job caring for my fur baby. Now I know when I travel she will be in good hands and well taken care of. Thank you Jorden.”


Colin P.Star Sitter

“Colin was prompt, very responsive and leaves the best post visit notes. Thank you, Colin. I will be sure to reach out the next time we need a sitter.”


Katrina R.Star Sitter

“Katrina was the best with my dog and cat. She kept me updated every visit and they seem comfortable with her. She fed them and kept the space clean for them! I would definitely book her again.”


Amanda S.

“Amanda came through for us last minute when we had a schedule change! She’s great with both our dogs and always shares updates on how the visit went. Having one anxious pup, we always appreciate hearing about their time together, and it’s been awesome to work with Amanda as our young rescue opens up and gets more confident. She’s also great at recognizing when our two dogs have different needs, and letting them do what’s best for them - today our young dog wanted to play outside and our senior dog wanted to snuggle on the couch after going potty because it’s cold and gross. Highly recommend working with Amanda!”


Tatiana V.
“Tatiana has been a pet owner for five years now. She takes really good care of our golden retriever named Grace. She shows compassion and affection all the time. She does well at walking her and picking up her feces.”


Kristen M.
“I can’t recommend Kristen enough! They have a natural gift with animals and treat every pet like their own. I’ve seen firsthand how gentle, patient, and attentive they are — whether it’s walking, feeding, playing, or just giving cuddles. Pets instantly feel safe and happy around them. They’re incredibly responsible, always on time, and follow instructions to a T. If you’re looking for someone trustworthy who will care for your pet with genuine love and attention, [Your Friend’s Name] is the one. Your furry family member couldn’t be in better hands!”


Miriam G.
About: I've care for dogs of all sizes and ages for 6+ years. I'm patient, loving, and experienced Wirth senior dogs, medications, and gentle outdoor routines. I'm currently work part-time, which gives me plenty of flexibility to care for pets, I'm available for boarding on weekends and during weekdays after 6 pm. Your pup will get plenty of attention, walks, and playtime. I have a fenced yard and one small dog who prefers her own space. To ensure safety, I separate visiting dogs when needed and always supervise interactions closely. I create a peaceful, clean environment where your pet will feel secure and cared for.


Kellee P.

“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.”


Daniel P.Star Sitter

“As always! Attentive, responsive and great with Baxter!”


Magdalena P.

“Maggie is great cat whisperer who easily relaxed a timid cat.”


Tatyana G.
About: I have had a dog since I was born. My dog and I grew up together, learning together. Saying that I’ve had my fair share of experience being with pets. I have always had the responsibility to learn how to take care of them and their needs and we can’t forget having fun with toys and walks. Recently my dog sadly passed away and I would love nothing more being pets again. I currently work night shift during the week. So I’ll be available during the day after 7 am for playtime and walks and making sure they are fed and whatever they may need. I also have the weekends off Unfortunately I do not have a fenced in yard but I do have lots of grass for them to run around in and live in a quiet neighborhood perfect for walks. Since I’m used to having two dogs in the home, I can accommodate most specific needs.


Melissa M.

“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.”


Alicia H.
About: I have loved and been taking care of dogs for as long as I can remember. Dogs are my life and I hope to be able to share my experiences with dogs with others. I am certified in Veterinary Technician Assistance and am working on my dog training certification and will be working toward a career in canine behavior. I have experience with all kinds of dogs with all kinds of personalities. I can't wait to meet and help care for your fur babies. I am currently a stay at home wife and mother looking to work with dogs. I am familiar with the daily care of a variety of animals. I trust all dogs as if they were my own. As an avid dog lover they are my life and I strive to provide each dog with the proper care and love they deserve. I have some basic training in canine first aid and a basic knowledge of canine CPR.


Joan F.

“Joan is an amazing petsitter who provides great updates and photos. Our kitty clearly enjoys these visits and is calm and not freaked out when we return. Highly recommended!”


Jennifer R.
About: I am a proud dog mom of 3 dogs and we use to have a cat. As you can imagine, I am a huge animal lover of all shapes and sizes! We have two pitbulls and a Chihuahua. Happy to do last minute drop ins to feed and love your pups if you are having a late day at work or weekends! Wednesdays, Fridays and weekends are the easiest days for me to care for your pets but I am flexible and can make anything work that you need. I will always care for your pup like it’s my own and make sure they are happy, safe, and loved. All dogs deserve that ❤️


Amanda E.
“Amanda was very good with watching my 1 and 1/2-year-old mix Hunter! She made sure that he got plenty of playtime and on any late shifts that I had at work she made sure to feed him the appropriate amount of food needed.”
Over 43 pet parents in Winchendon have booked pet sitting
Winchendon pet parents share their Rover experiences
Popular requests near you
Select a filter and find qualifying Winchendon sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for pet sitting in Winchendon is $25
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 pet 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.
Sitters in Winchendon average 7 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchendon on Rover as of Aug 2025 was about $25 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 79 pet sitters in Winchendon. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 97% of Winchendon pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winchendon.
Rover makes it easy to find Winchendon pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 79 pet sitters in Winchendon on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
