Dog Sitting in Winchendon
Book a Winchendon dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Winchendon dog sitters

“Nikki was able to come by and entertain Quinn while I enjoyed a routine colonoscopy. I was glad to find him happy and exercised, as I need to rest for part of the day.”


About: I have cared for my coworker’s small dog and 2 cats over a long weekend (2 nights and three days). Pixie and I went for walks, and I made sure her food and water bowls were refilled and fresh and clean daily. I also kept the yard clean after her potty breaks! I am available for evening visits during the week and weekend, when you are in a pinch and need someone to take your dog for a walk and have a potty break. I am typically available weekday evenings after 5. I am available to travel to your home and care for your sweet pup where they feel most safe and comfortable! I can make sure your small dog is well-fed, walked, played with, and feels comfortable while you're away. I'm attentive, gentle, and always follow specific routines or instructions to help your pet feel safe, cared for, and loved.

“Fawn is amazing and very communicative, and took great care of my cats. I felt very safe leaving them in Fawn’s care and will definitely use them again.”


“Angelita was a great sitter for my 3 cats! She was timely and followed all instructions to a T. I received great updates and photos with each visit.”


“This was my first time using Rover for my 3 cats. 2 cats need medication. Yadi was responsible for 2 automatic litter boxes and 1 regular litter box, food, meds, and 2 water fountains. I was very pleased with her communication for every visit. I’ve already asked to rebook her!”


About: I have been caring for pets for nearly all my life. From cats and dogs to rodents and eveything in-between, I feel comfortable taking care of all animals at any age. I work full time Monday through Friday from 7am-3pm but I am available after 3pm and overnight on weekdays. Weekends I'm entirely available during the day and overnight. I am unable to care for pets in my home but I can take care of your pets in your home. I love playing with pets in a backyard or taking dogs for walks.

About: I have been pet sitting for many years now. Started out as helping out family and friends in high school and college and has evolved to much more over the years. I also have 8 years of experience owning my own dogs. I have cared for dogs of all ages and sizes, cats, lizards, and turtles. I am comfortable with transporting pets to vet or grooming appointments, bathing, brushing, and brushing teeth for dogs, feeding, giving topical and oral medication, walking, playing, picking up after, cleaning litter boxes. I am genuinely happiest when I am with animals so getting to spend time with your fur babies would be my absolute pleasure! I will treat your pets as my own while they are in my care and I will always make sure they are kept happy and safe. I work a 9-5 Monday - Friday with a hybrid schedule. I typically work from home Wednesday and Fridays. I am available for daycare bookings on my WFH days, overnight bookings any time and walks/drop-ins in the evenings & weekends. For overnight bookings during the week, on my in-office days, my brother is available to check in on the pups at home and give them mid-day bathroom breaks and some company. I have a new fence being put in for the yard at the moment and in the meantime, I have extra long leashes so the pups can still safely explore and get some exercise in the yard. I have 2 pups of my own to keep your pet(s) company and have lots of playtime with. I have plenty of space throughout the house to keep dogs separated while I am not home and have pet cameras to keep my eye on them! I also have 2 large crates and 1 small crate if needed. I prefer to sit for dogs that are crate trained to ensure extra safety but this can be discussed during the meet and greet! My 65lb male dog does not always enjoy other males that are larger than himself in the house but we can still have a meet and greet to check, with this in mind! I always suggest sending your dog for an overnight stay with their doggy bed/favorite blanket and a favorite toy to make them the most comfortable!

“We reached out to Dayana on short notice and she jumped right in to help! She took wonderful care of our big guy and sent pictures of him on every visit! We arrived home to happy pup and a tidy space. Dayana’s communication was always fast and friendly. We had a great time on vacation knowing Sam was being well taken care of :))))”


“Thank you for looking after our pet even with short notice on a holiday weekend!”



About: I have walked dogs of all different sizes, ages & breeds. I have also administered medications ( oral & topical ), changed bandages. I've loved animals my entire life & my client's pups/pets become "my" pets..in other words, I love them like they were my own. * I prefer to do "Meet & Greets" with potential clients and their pets prior to taking the "job", so not only do I and the pets get to meet, but the pet parent(s) & I can also meet & discuss any schedules, routines, etc. as well as go over any questions. I want to not only be comfortable with them, but I want the pet parent(s) & of course, the pets, to be comfortable with me as well. P.S. I’ve worked in many horse barns in my 20’s, so don’t hesitate to reach out for help ( even if it’s a one time thing :) I’m pretty available due to being on Social Security ( due to a major car accident in 2009), so I do this to not only supplement my income but because I love animals & it also helps me in multiple ways ( mentally, physically, etc.) I treat your home like my home in the sense that I become protective of the space ( & pets of course), I don’t like random people showing up/trying to enter the home without my hearing Directly from the homeowner. After I’m familiar w/ the way things typically are ( ex. what vehicle(s) are routinely there/not there then a “random” vehicle is suddenly there, I will be suspicious & notify the pet parent/home owner right away to make sure it’s ok to be there).

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: Hello my name is Becky I am a special education teacher who finds joy in spending my free time with all kinds of animals. There is nothing better than the look of love from an animal when you’re spending time together. As a pet owner I understand the importance of spending quality time with my animals and making sure they feel loved. I love being outdoors hiking, kayaking and getting exercise. I am patient and kind and have experience with many different kinds of dogs. I love the outdoors and would love to have some fun with your pet. I am high energy and excited to have fun with your pet. As a precious dog owner I understand the importance of quality love and affection for your fur baby I look forward to providing the love and attention they deserve. I am a special education teacher by day and bartend some nights my availability reflects when I am free. I understand life is busy and will help whenever I can. I am very attentive and love spending quality time with animals and I’ll send lots of pictures. This is your baby you tell me what you need!!

“Mccenzy came over to play with our (high maintenance, socially selective) pup before she sits for a week for us while we’re away. They became fast friends and she followed directions perfectly to make sure our pup felt comfortable with someone knew in our home.”


About: Whether it's energetic puppies or mellow senior dogs, I provide dependable, loving care tailored to each pup’s needs. From daily walks to couch cuddles, I treat every dog like they’re my own. What sets me apart? A calm, reliable presence, lots of experience, and a genuine love for all things canine. Pet care fits perfectly into my routine with availability in the mornings, evenings, and often during the day. I work at Franklin Pierce University, but I have flexibility in my daytime schedule—especially outside of game days—so I can accommodate midday visits when needed. Your pup will get plenty of love and attention before and after work, and I’m happy to adjust as my schedule allows! Whether I’m caring for pets in my home or yours, their safety and comfort are always my top priorities. I follow any routines or instructions you provide closely to ensure your dog feels secure and well cared for. I create a calm, pet-friendly environment with plenty of affection, supervision, and playtime. I also respect your space—leaving everything just as I found it—and keep you updated with messages and photos so you can feel at ease while you're away.

“Haley is wonderful! She goes above and beyond and is very communicative. Highly recommend!”


“Nikki did a wonderful job checking in on my two cats while I traveled for a few weeks—she was reliable, prompt, and great with my pets. Would book again and recommend!”


“Kayla did amazing taking care of cat Luna while we were away to El Salvador! Whole week without signal but Kayla kept us updated regardless, thank you again!”


About: I have a plenty of experience with dog sitting and walking and am more then excited to share my experience with your furry friends and provide the best and safest service I can! I’d like to have the pet owners keep in mind that I will need a flexible schedule and that I will let you know if a certain time or day may not work for me that week but I will try my best to make as many appointments as I can! I’m only comfortable with taking care of pets at a clients home but I will assure you that I will follow instructions that the client may leave for me and due my best to keep there fur baby safe and comfortable!

“Lauren arrived on time and was wonderful with Trixie. I highly recommend her.”


About: I have had dogs in my life since I was born and currently have 3 dogs. I’ve owned all different kinds of breeds and taken care of more. I know how to handle multiple dogs at a time and I am an active person who will go above and beyond to take care of your pet. Pets have been a big part of my life since I was born. I am currently working part time as I am currently student so I have a lot of time on my hands this summer. Your pet will feel at home and comfortable. I will make sure their schedule stays the same and they are fed and walked at the time given.
Loving dog sitters in your neighborhood
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Nikki M.Star Sitter

“Nikki was able to come by and entertain Quinn while I enjoyed a routine colonoscopy. I was glad to find him happy and exercised, as I need to rest for part of the day.”


Rebecca S.
“I've seen firsthand how great Rebecca is with animals since she’s cared for her own cat, Lola, with love and attention, and has experience looking after other small cats and animals as well. She's gentle, respectful of each pet’s unique personality, and knows how to balance affection with boundaries. She’s no stranger to Churus or other pet treats and will happily play with your pet if they need some fun or stimulation. Plus, she’s tidy, reliable, and never afraid to get her hands dirty. As a bonus, you might even get a little drawing of your pet (she’s a talented artist too!). Anyone would be lucky to have her as a sitter.”


Fawn W.Star Sitter

“Fawn is amazing and very communicative, and took great care of my cats. I felt very safe leaving them in Fawn’s care and will definitely use them again.”


Angelita T.

“Angelita was a great sitter for my 3 cats! She was timely and followed all instructions to a T. I received great updates and photos with each visit.”


Yadira W.

“This was my first time using Rover for my 3 cats. 2 cats need medication. Yadi was responsible for 2 automatic litter boxes and 1 regular litter box, food, meds, and 2 water fountains. I was very pleased with her communication for every visit. I’ve already asked to rebook her!”


Emily E.
“Emily is great with all sorts of animals. I've seen her bottle feed 1 week old kittens to maturity and health and I know she works with rodents professionally as well. As an animal lover myself I know she loves dogs.”


Danielle D.
“We had danielle watch our 3 year old pitbull/lab mix for three nights when we went away. She was nice enough to send us pictures of Kobe playing outside and snuggling on the couch with her while we were gone, which was a plus so I wasn’t worrying constantly! He came back to us all tired out, she took such great care of him like he was her own dog. I felt so comfortable leaving him with her, I will 100% go back to her for our next trip! Highly recommend!! ?”


Dayana C.Star Sitter

“We reached out to Dayana on short notice and she jumped right in to help! She took wonderful care of our big guy and sent pictures of him on every visit! We arrived home to happy pup and a tidy space. Dayana’s communication was always fast and friendly. We had a great time on vacation knowing Sam was being well taken care of :))))”


Katryna K.

“Thank you for looking after our pet even with short notice on a holiday weekend!”




Nichole S.
“Nichole has been taking care of pets for me for more than a decade. She's very caring, punctual, and my animals have just loved her! She has a gentle touch and the best rapport with animals of any human I've ever known!”


Robin K.
“Hi Robin K would be an awesome sitter or dog walker. I know she has a love of animals & a great sense of responsibility for caregiving. I would hire her in a minute.”


Becky T.
“I have known Becky E for almost two years. She is naturally caring at heart. She is selfless and always helping others both humans and animals. My animals love Becky. My dog wants to hop in her car as soon as she pulls in. Becky and my dog have a natural bond. I also have two cats, one typical and one who is very skittish. Becky took her time and slowly created a relationship with this cat. Becky is trustworthy, reliable, kind, caring and nurturing. Clients will fall in love and might be a little jealous if their pets like her more. My pets would gladly have me go on vacation just so they can be taken care of by Becky.”


Mccenzy M.

“Mccenzy came over to play with our (high maintenance, socially selective) pup before she sits for a week for us while we’re away. They became fast friends and she followed directions perfectly to make sure our pup felt comfortable with someone knew in our home.”


Danielle M.
About: Whether it's energetic puppies or mellow senior dogs, I provide dependable, loving care tailored to each pup’s needs. From daily walks to couch cuddles, I treat every dog like they’re my own. What sets me apart? A calm, reliable presence, lots of experience, and a genuine love for all things canine. Pet care fits perfectly into my routine with availability in the mornings, evenings, and often during the day. I work at Franklin Pierce University, but I have flexibility in my daytime schedule—especially outside of game days—so I can accommodate midday visits when needed. Your pup will get plenty of love and attention before and after work, and I’m happy to adjust as my schedule allows! Whether I’m caring for pets in my home or yours, their safety and comfort are always my top priorities. I follow any routines or instructions you provide closely to ensure your dog feels secure and well cared for. I create a calm, pet-friendly environment with plenty of affection, supervision, and playtime. I also respect your space—leaving everything just as I found it—and keep you updated with messages and photos so you can feel at ease while you're away.


Haley B.

“Haley is wonderful! She goes above and beyond and is very communicative. Highly recommend!”


Nicolina S.

“Nikki did a wonderful job checking in on my two cats while I traveled for a few weeks—she was reliable, prompt, and great with my pets. Would book again and recommend!”


Kayla M.

“Kayla did amazing taking care of cat Luna while we were away to El Salvador! Whole week without signal but Kayla kept us updated regardless, thank you again!”


Leah W.
About: I have a plenty of experience with dog sitting and walking and am more then excited to share my experience with your furry friends and provide the best and safest service I can! I’d like to have the pet owners keep in mind that I will need a flexible schedule and that I will let you know if a certain time or day may not work for me that week but I will try my best to make as many appointments as I can! I’m only comfortable with taking care of pets at a clients home but I will assure you that I will follow instructions that the client may leave for me and due my best to keep there fur baby safe and comfortable!


Lauren B.

“Lauren arrived on time and was wonderful with Trixie. I highly recommend her.”


Paige S.
“Paige has dog sat for me several times. She does over nights and just letting them out going for walks or just coming by to me if I dot. Have time for play time. I know she just graduated with a biology degree and is looking to got to vet school so she is perfect. She is timely and sweet to Our dogs. I love her! She is the best”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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!
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn't happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winchendon.
Rover makes it easy to find Winchendon dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
