Pet Sitting in Winchendon

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Sitter Profile Image: Allegra  M.
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Sitter Profile Image: Allegra  M.
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1. Allegra M.

Stress Free Dog Care
Leominster, MA, 01453
17.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
14 repeat clients
from
$20
per visit
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Allegra did an awesome job taking care of Luna. Would highly recommend her

Confirmed availability: Juneteenth
Sitter Profile Image: Nikki M.
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Sitter Profile Image: Nikki M.
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2. Nikki M.

Follow Me on IG: TheDogMama603
Peterborough, NH, 03458
18.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
123 reviews
44 repeat clients
from
$18
per visit
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Nikki was an absolute dream come true. She took excellent care of our dogs while we were away. Consistent updates with pictures showed how happy our fur babies were! I highly recommend Nikki!

Sitter Profile Image: Devon P.
Sitter Profile Image: Devon P.

3. Devon P.

Would love to care for your pets!
Winchendon, MA, 01475
0.2 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
39 reviews
16 repeat clients
from
$25
per visit
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Devon is kind and patient, and very reliable. It feels great to know my dog is being well taken care of while we are at work. I would recommend her!

Confirmed availability: Juneteenth
Sitter Profile Image: Mariah J.
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Sitter Profile Image: Mariah J.
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4. Mariah J.

I enjoy long walks with your pets🐾
Fitchburg, MA, 01420
13.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
99 reviews
47 repeat clients
from
$20
per visit
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Mariah is absolutely amazing! I was in a bind with work and my dog being heat I didn’t have many options but when I reached out to Mariah she immediately got back to me and did multiple drop ins. I felt at ease knowing my Piper was taken care of! I’ll be using her again for sure!

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Sitter Profile Image: Jillian D.
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Sitter Profile Image: Jillian D.
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5. Jillian D.

Animals of all kinds welcome!
Winchendon, MA, 01468
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
237 reviews
105 repeat clients
from
$17
per visit
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Jillian was very responsive from the moment we requested a sitter and with every visit. Our super shy black cat even came out to say hi with her visits and she doesn’t like strangers at all! She did things to benefit our babies - it was like we weren’t even gone. Would highly recommend!

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Sitter Profile Image: Katrina A.
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Sitter Profile Image: Katrina A.
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6. Katrina A.

Chizer Mom
Gardner, MA, 01440
8.3 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$20
per visit

About: Hello, my name is Katrina and Gizmo Binx is my 8 month old minischnauzer/ chihuahua mix. I have had dogs and cats my entire life. I have cared for elderly dogs and cats and also special needs pets. We would love to care for your dog and keep them company. Gizmo and I like to take walks in our neighborhood and occasionally visit the dog park in town. Gizmo is an active little man that loves to play fetch and wrestle with his kitty brother but also enjoys snuggle time. He would love to make some new friends. We are working hard on manners and it is paying off. Socialization is key. So please consider us for your next outing or vacation. Please let us know if we can help you out. We have an open schedule so drop us a line! Thank you My schedule is extremely flexible. I can work when I have availability to. Feel free to request most any hours. I would rather spend my time with the animals. I also have flexibility when it comes to how you have trained your pup. Your house your rules. This goes for house sitting, walks and drop ins.

Sitter Profile Image: Danielle D.
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Sitter Profile Image: Danielle D.
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7. Danielle D.

Your pets are safe with me!
Gardner, MA, 01440
7.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$20
per visit
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Danielle did an excellent job highly recommend very personable and professional

Confirmed availability: Juneteenth
Sitter Profile Image: Leeha H.
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Sitter Profile Image: Leeha H.
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8. Leeha H.

Rover 101
Tender love and care is my game ❤️
Gardner, MA, 34746
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
8 repeat clients
from
$28
per visit
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Lucy adores her. Patient and caring with pets

Confirmed availability: Juneteenth
Sitter Profile Image: Amanda H.
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Sitter Profile Image: Amanda H.
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9. Amanda H.

Your pet’s home away from home
Winchendon, MA, 01475
2.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
5 reviews
from
$22
per visit

Amanda has taken care of my cats, she not only feed them but took time to play with them. We have also see her with her own animals and she takes very good care of them.

Confirmed availability: Juneteenth
Sitter Profile Image: Amanda S.
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Sitter Profile Image: Amanda S.
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10. Amanda S.

8yrs experience as Vet Tech - WFH
Rindge, NH, 03461
3.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
10 repeat clients
from
$25
per visit
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Amanda continues to do an amazing job getting our nervous young rescue dog to trust her (and taking care of our sweet senior dog, too). I cannot recommend her enough!

Confirmed availability: Juneteenth
Sitter Profile Image: Megan L.
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Sitter Profile Image: Megan L.
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11. Megan L.

All dogs are good dogs!
Ashburnham, MA
6.0 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$17
per visit

Megan has taken care of my dog Zoey on multiple occasions. Zoey absolutely loves her! With Megan, I know that my dog is going to be well taken care of and have a great time with her. She absolutely loves dogs and is a very responsible and trustworthy person to have looking after your pets. She’s my first choice whenever I’m away! Bonus points: She has a background in animal behavior so she knows how to interact with your dog.

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Sitter Profile Image: Kiley R.
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Sitter Profile Image: Kiley R.
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12. Kiley R.

Vet tech that loves pets
Ashburnham, MA, 01430
8.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$15
per visit
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Kiley is an angel! She saved the day for and I am so unbelievably grateful! 10/10!

Sitter Profile Image: Ellie M.
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Sitter Profile Image: Ellie M.
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13. Ellie M.

Pet Care Extraordinaire
Templeton, MA, 01468
9.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
3 repeat clients
from
$22
per visit
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Thank you Ellie! You are truly a Christmas miracle! Ellie was patient and kind with Kenzie and Tucker. She understood their hesitation and took her time to make them comfortable. We will definitely be using Ellie again. 🙂

Confirmed availability: Juneteenth
Sitter Profile Image: Haley B.
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Sitter Profile Image: Haley B.
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14. Haley B.

Wag More, Worry Less 🐶 🐱
Ashburnham, MA, 01430
7.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$35
per visit
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Haley is wonderful! She goes above and beyond and is very communicative. Highly recommend!

Confirmed availability: Juneteenth
Sitter Profile Image: Samuel L.
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Sitter Profile Image: Samuel L.
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15. Samuel L.

dog physical activity specialist
New Ipswich, NH, 03071
8.9 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$15
per visit

Sam Larareo is by far my first choice whenever we need drop in visits and walks for our little pup! We have used his service on several occasions, especially if we need to go out of town for a short period and can’t take our Jackie. He is great with our dog and he communicates on a regular basis when we have to leave for a short time. Above all, Sam is trustworthy, and our pup loves his visits. would be happy to provide personal references upon request.

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Sitter Profile Image: Adrianna L.
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Sitter Profile Image: Adrianna L.
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16. Adrianna L.

No dog too big or small!
Winchendon, MA, 01475
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$20
per visit

Wouldn’t trust my dog with anyone other than Adrianna! She treats my dog like one of her own pups and keeps me updated whenever she has her. My dog always comes home exhausted after a stay with Adrianna due to all their adventures and exercise she gives them!

Sitter Profile Image: Ashley H.
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Sitter Profile Image: Ashley H.
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17. Ashley H.

🐾Expert Pet Care in Your Home!
Winchendon, MA, 01368
1.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
11 repeat clients
from
$23
per visit
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I’m so happy to have found Ashley for regular visits for my two senior kitties! She is very caring, respectful, and gave great reports and pictures from the first visits. She has a calming energy - one of my cats always hides from strangers and even people he has seen before, but he didn’t run away at the meet and great or visits. I would definitely recommend Ashley to anyone who needs a responsible and dedicated sitter.

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Sitter Profile Image: Luiz B.
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Sitter Profile Image: Luiz B.
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18. Luiz B.

Rover 101
we love animals, they're family too
Gardner, MA, 01440
8.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
136 reviews
26 repeat clients
from
$35
per visit

You could not find a better place to leave your dog. Not only the place is great, but also the family! Definately recommend it!!! Very happy!!!

Sitter Profile Image: Jordan H.
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Sitter Profile Image: Jordan H.
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19. Jordan H.

All fur babies lives matter!
Ashburnham, MA, 01430
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$30
per visit

Jordan has cared for my two dogs, (a Chihuahua mix and a Pit Bull mix), many times. He is clearly an animal lover. My dogs are always happy to see him. He has a super calm energy which seems to put animals at ease. Plus my dogs really listen to him - better than they listen to me! I also appreciate that Jordan is consistently reliable and professional. I highly recommend him as a pet sitter and/or walker.

Sitter Profile Image: Casey D.
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Sitter Profile Image: Casey D.
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20. Casey D.

Reliable care on short notice.
Winchendon, MA, 01475
1.8 mi. away
House Sitting, Drop-In Visits
1 review
from
$20
per visit

I highly recommend Casey as a pet and house sitter. Our two terriers and two cats adore him, and it seems the feeling is mutual. Beyond his genuine care for our pets, Casey treated our home respectfully and kept everything tidy upon our return. Knowing our animals and home were under Casey's watch provided unparalleled peace of mind during our vacation. His blend of responsibility and compassion makes him my first choice for a sitter any time we travel. Seriously can't recommend him enough!

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Winchendon Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winchendon are rated on average 5 out of 5 stars based on 32 reviews.

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Winchendon:


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Winchendon pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Winchendon, MA, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Winchendon pet sitters and avoid the kennel.

Drop-In Visits