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

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Amadie C.
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Amadie C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
14 reviews
4 repeat clients
2 years of experience
Swanzey, NH, 03446

Can I give Amadie 10 stars??? We had recently lost one of our kitties and had a 10 day vacation scheduled plus we had moved so needed a pet sitter for our senior, very shy kitty. Amadie was the perfect fit! Our senior kitty warmed up to her and she actually let Amadie pet her a few times. This was a first for anyone besides me or my husband! The patience, love and care she showed to Luna was beyond anything we ever expected. She also was so caring for our home and reached out with questions. Amadie communicated with us daily, pictures and updates. We will definitely ask Amadie to care for Luna again.

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Martha S.
Sitter Profile Image: Juliana G.
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Juliana G.
$34
total per visit
5.0 out of 5 stars
3 reviews
1 repeat client
30 years of experience
Westminster, MA, 01473

About: Hi all! I am a stay at home mommy of two adorable and sweet teens . We are a family of animal lovers. I am a pet owner through all my life. I currently have 5 cats.. and one gentle husky/Collie sweetest Puppy ever who craves for companionship <3 I have a nice area for my cats (also a nice fenced cat patio) and a decent size back yard. I live on quiet dead end st. If your dog is boarding with us. At night time, He will have three options. Have its own crate, Or it can be free (as long as it is house trained and won't chase after my other fur-babies -cats- ??) Orrr Sleep in my bed with all my other fur-babies. If you need me to come to your house. I could also do that as well and provide kisses, hugs, playtime, food, water and cleaning. (Special instructions welcome) Oh and please I could also take care of and board Cats or other pets too!!! I love them all and it’s going to be my pleasure! ( I do have a separate area for all my cats and it’s full of fun stuff and catnip ??. But they do have full access of the house at all time) No outdoor cats please. Please come visit me and my fur babies! I am a stay at home mom. And I have plenty of free time in my hands. It would be a pleasure for me and my teens to take care of your pet. It will depend on the client's preference. I could do crating, or free run of the house. (If pet is house trained). Nice decent yard and safe neighborhood.

Sitter Profile Image: Shanna A.
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Shanna A.
$62
total per visit
20 years of experience
Winchendon, MA, 01475

About: I’ve always owned dogs and cats! Right now I have a male German shepherd! Previously I had a female German shepherd. I would love to help anyone who’s in need of care/play for their dog/s and or cat/s! I currently work 3, 12hr overnights. I will be available for mornings and later afternoons/evenings! Let me know what the needs are to take care of your pets! I will not be able to board at my house. I will only do drop in visits for care needs and let outside to do their business.

Sitter Profile Image: Jeffrey W.
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Jeffrey W.
Star Sitter
$23
total per visit
5.0 out of 5 stars
42 reviews
16 repeat clients
12 years of experience
Sterling, MA, 01564

Jeffrey is responsible, loving with dogs, punctual, and careful! I highly recommend him. We will definitely work together again.

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Patricia R.
Sitter Profile Image: Haley C.
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Haley C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
92 reviews
35 repeat clients
17 years of experience
Hinsdale, NH, 03451

Haley was great! She communicated clearly, quickly and took great care of my cat Callie. I have already booked her for my next out of town trip.

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Azariah A.
Sitter Profile Image: Elizabeth N.
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Elizabeth N.
$23
total per visit
4.9 out of 5 stars
50 reviews
27 repeat clients
7 years of experience
Barre, MA, 01005

She is very sweet and great with my furry pups. Very convenient to go online and book with no confusion She is coming again in August for house sitting as well.

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Becky L.
Sitter Profile Image: Patricia H.
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Patricia H.
$28
total per visit
1 repeat client
40 years of experience
Princeton, MA, 01541

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! 😂

Sitter Profile Image: Emily M.
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Emily M.
$29
total per visit
4.8 out of 5 stars
22 reviews
8 repeat clients
8 years of experience
Marlborough, NH, 03455

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.

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Brian B.
Sitter Profile Image: Robin K.
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Robin K.
$34
total per visit
50 years of experience
Athol, MA, 01331

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.

Sitter Profile Image: Mackenzie H.
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Mackenzie H.
$23
total per visit
5 years of experience
Gardner, MA, 01440

About: Pet Care Experience: I’ve been caring for animals my whole life! 🐾 From my time in 4H, where I competed with my own animals, to looking after pets of all kinds, I bring experience, dedication, and a deep love for animals. Whether it’s caring for energetic puppies, providing companionship for senior dogs, or making sure your pet gets the right amount of playtime and love, I’m here for it! ❤️🐶 I specialize in: ✔️ Puppy care & basic training 🍼🐕 ✔️ Senior pet support 🦴🐾 ✔️ Administering medications (oral & topical) 💊 ✔️ Walks, playtime & belly rubs! 🏃‍♀️🎾 Your pet will be treated like family while you’re away! 🏡💖 Schedule: 🐾 Pet care is my #1 priority! 🐾 I have a flexible schedule since I’m currently in school, which allows me to accommodate morning, afternoon, and evening visits. Whether your pet needs a quick potty break, a midday walk, or overnight care, I can work with your schedule! 📅🐕 Safety, Trust & Environment: I believe pets are happiest in their familiar environment, which is why all care is provided in your home. 🏡💙 Here’s what I offer: 🐾 Regular check-ins for food, water & potty breaks 🐾 Daily walks tailored to your pet’s needs 🦮🚶‍♀️ 🐾 Playtime to keep tails wagging 🎾🐕 🐾 Overnight stays for extra comfort & security 🌙🐾 I always ensure pets feel safe, loved, and comfortable while you’re away. 🐾💖

Sitter Profile Image: Dawn L.
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Dawn L.
$34
total per visit
30 years of experience
Phillipston, MA, 01331

About: Extensive, daily, hands-on experience with animals of all different kinds, dogs, cats, horses, goats, sheep, chicken & bunnies. Currently own and care for four dogs, three cats, 16 horses, goats, and sheep, chicken and bunnies. Always Work closely with our vet to provide optimum healthcare for all of our animals. current daily routine includes daily Farm care for our horses , sheep, goats, and chickens +4 dogs & three cats. We have plenty of availability, knowledge, and experience to take care of your four legged family members as well. I am happy to provide daily visits, daily walks and other needed services throughout the week. 30+ years of animal care experience to offer. From farm animal care to house pets to fostering many puppies and dogs over the years. Plenty of experience with senior dogs to puppies and kittens. Experience with special diets and medication’s.

Sitter Profile Image: Maria M.
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Maria M.
$23
total per visit
1 year of experience
Peterborough, NH, 03458

About: I’ve taking care of different kinds of dogs even puppies that family and friends had me help it with a few years ago till now. so I am available to help during the week and some weekends as well I will start be available for weekends in November it. Ask me any questions you may have. I am here Hi! I’m a dependable and loving pet sitter who enjoys spending time with animals of all personalities. I’m patient, attentive, and committed to keeping your pet safe, happy, and well cared for. You can trust me to treat your pet like family.

Sitter Profile Image: Nadine N.
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Nadine N.
Star Sitter
$36
total per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
20 years of experience
Keene, NH, 03431

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!

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Tim H.
Sitter Profile Image: Katie D.
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Katie D.
$23
total per visit
27 years of experience
Westminster, MA, 01473

About: I grew up with labs, mastiffs, collies, and shepherds. I treat my dogs better than my family at times! Play, comfort, and love are staples. I work full-time during the week, but am home most weekends with my 11 month old socialized lab. My dog receives daily exercise and active play and yours will too! I will ensure your dog’s safety and your peace of mind by taking them out on leash for walks and bathroom breaks. I value active play time and also work in rest times.

Sitter Profile Image: Kayla G.
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Kayla G.
$28
total per visit
5.0 out of 5 stars
20 reviews
8 repeat clients
4 years of experience
Fitchburg, MA, 01420

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.

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Jonie L.
Sitter Profile Image: Kayla M.
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Kayla M.
$28
total per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Ashburnham, MA, 01430

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!

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Amy P.
Sitter Profile Image: Bradleigh P.
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Bradleigh P.
$28
total per visit
4.9 out of 5 stars
12 reviews
7 repeat clients
4 years of experience
Fitchburg, MA, 01420

This was my first time using a pet sitting service so I was pretty nervous. Bradleigh is super friendly and outgoing and made this experience stress free! I highly recommend Bradleigh and wouldn't hesitate to choose her again in the future.

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Mary L.
Sitter Profile Image: Chastity N.
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Chastity N.
$18
total per visit
4 years of experience
Gardner, MA, 01440

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 currently work at an animal shelter. I'm currently working 2 part time jobs. Wednesdays, Saturdays and Sundays availability with the possibility of Mondays. I'm available for dog walking, trips to the dog park and pet sitting. 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.

Sitter Profile Image: Olivia B.
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Olivia B.
$32
total per visit
10 years of experience
Phillipston, MA, 01331

About: I have grown up with dogs and when adopting our most recent pup, Jax, I quickly realized he was a pup that required more than just a couple walks a day, so we got into running together daily. I offer dog running or walking and look forward to meeting your fur babe(s)! I am currently available Mondays, Thursdays, Saturdays and Sundays for dog walks, runs and drop-in visits and pet sitting Saturday thru Monday. I currently have limited availability Tuesdays, Wednesdays, and Fridays but would be happy to discuss scheduling with you! I am very reliable and I will provide water and treats as needed. I will show up regardless of snow or inclement weather. We can customize walks or runs based on your preference of on vs off leash.

Sitter Profile Image: Katie C.
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Katie C.
$28
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
2 years of experience
Gardner, MA, 01440

About: I have had dogs and cats, and also a horse for most of my life! My current dog is a 10 year old rescue from Tennessee, and he’s the love of my life. I’ve worked very hard with a trainer with my pup, so I have some experience there. I volunteered at the humane society and ASPCA for many years off and on, and I also fostered dogs throughout college. Safe to say I have plenty of hands on experience with all sorts of pets :). I am working full time, but I have a somewhat flexible schedule! I have plenty of time throughout the day to spend some time with whatever pet needs the attention! In my home, my dog is pretty spoiled :). He is my main priority, as it is just him and myself, and it’s been that way for years! As far as other people’s pets in their home, I will follow any instructions in detail that are provided, but above all I will make sure the pet is happy and healthy and comfortable!

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Winchendon dog parents share their Rover experiences

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5.0 out of 5 stars

Amanda is a thoughtful and capable pet sitter. Also helped with our mail and feeding my wild critters that visit the yard, too. Highly recommend. Very trustworthy in our home.

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Laura B.
Drop-In Visits
5.0 out of 5 stars

Jorden is amazing as always, but this time was extra helpful coming to drop in on less than a day’s notice when something came up for my family!!

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Kellie F.
Drop-In Visits
5.0 out of 5 stars

Devon was great visiting our home with our nervous pups that are never separated from their humans. The pictures and updates were extremely reassuring and gave us peace of mind while away for the weekend! We will absolutely reach out again,

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Amanda H.
Drop-In Visits
5.0 out of 5 stars

Amanda is so patient and so understanding to my badly behaved Delta. She is a pleasure to work with and is an excellent knowledgeable resource as she’s a vet assistant

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Chris S.
Drop-In Visits
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If you’re searching for a Winchendon dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

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.