Pet Sitting in Winchester

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

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1. Cheryl Verified Background Check

Experienced and compassionate.

Woburn, MA, 01801

Drop-In Visits, Dog Walking

"Cheryl has been terrific - so communicative and friendly! We love getting updates from her whenever she visits and our little fluff ball loves playing with her… (more)"

Confirmed availability
 Easter weekend
2. Amber Verified Enhanced Background Check

Former Vet Student & Shelter Worker

Arlington, MA, 02476

Drop-In Visits, Dog Walking

"Amber was amazing with our two cats while we were away for an extended trip! One of our cats requires twice a day medication and we were completely at ease kno… (more)"

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3. Anabelle Verified Background Check

Fun-Loving Dog Walker

Medford, MA, 02155

Drop-In Visits, Dog Walking

"In the time that I’ve known her, Anabelle has always exemplified the characteristics of someone who is thoughtful, caring, and attentive. I’ve seen these trai… (more)"

Confirmed availability
 Easter weekend
4. Sally Ann H Verified Enhanced Background Check

I'm honored to care for your bestie

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Sally has saved family vacations for me! I used to worry so much about my elderly, disabled cats that it would ruin the fun of going out of town. Sally took su… (more)"

Confirmed availability
 Easter weekend
5. Callie Verified Background Check

Friendly and responsible student

Somerville, MA, 02144

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Callie had a dog growing up and she still loves to cuddle and take care of her two family dogs Marty & Milo. She loves taking them for walks, throwing balls f… (more)"

Confirmed availability
 Easter weekend
6. Angela Verified Background Check

Active, friendly neighbor!

Belmont, MA, 02478

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

"Angela is a great sitter - very responsive with great communication and always happy to send photos. I've used a number of sitters for my dog in the past but w… (more)"

7. Kiki Verified Background Check

Fun and active animal Lover!!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Kiki was excellent at handling and listening to instructions for my dog. When my dog sees Kiki, he instantly knew he was going for a walk or getting a treat fr… (more)"

Confirmed availability
 Easter weekend
8. Kimm & Kenn Verified Background Check

Love dogs, love to walk!

Woburn, MA, 01801

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"As we just moved to a new place and did not find a cat sitter yet. After reading the positive reviews we decided to reach out to Kimm & Kenn S. Kimm has been s… (more)"

9. Hallye Verified Background Check

Every weather walker, rain or snow!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Incredibly respectful and reliable. My skittish kitten took to her. Highly recommend Hallye. (more)"

Confirmed availability
 Easter weekend
10. Olivia Verified Enhanced Background Check

Active, dog lover!

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Olivia is one of the most responsible and organized people I know, and she's also such a dog-lover! Would trust her with my dog anyday. She's more than capable… (more)"

Confirmed availability
 Easter weekend
11. Christina Verified Background Check

Lover of all things dog.

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: Dogs are my favorite kind of people, what can I say. I have years of experience both as a dog owner and dog sitter. I do not have any pets or childre… (more)

Confirmed availability
 Easter weekend
12. Susan Verified Background Check

Specializing in keeping pets happy!

Winchester, MA, 01890

Dog Boarding, House Sitting, Drop-In Visits

"I highly recommend Susan to care for your pets. She has been taking care of my two red Australian labradoodles for eight years when we are away. Sometimes my d… (more)"

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13. Jackie Verified Background CheckRover 101

Active couple, love the outdoors!

Melrose, MA, 02176

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I have seldom met anyone with as much love in her heart for dogs, as Jackie. She owns an Irish Terrier, which she cherishes, and treats like a child. Her conce… (more)"

Confirmed availability
 Easter weekend
14. Angela Verified Enhanced Background CheckRover 101

Happy pets make for happy owners!

Medford, MA, 02155

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Angela made me feel comfortable right away with our older dogs. She is a knowledgable, kind-hearted dog lover. She is very reliable and I know my dogs are alwa… (more)"

Confirmed availability
 Easter weekend
15. Carlena Verified Enhanced Background Check

Loving, Hard Working Student

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Carlena did an amazing job taking care of Louie! Very courteous, respectful, and friendly. Louie was well taken care of and knowing that kept my mind at ease d… (more)"

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16. Erin Verified Background Check

I have a love for all animals!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Erin is a great sitter! I always love seeing her messages and photos, it makes us miss the pets but also feel good knowing they’re safe and had a fun play date… (more)"

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17. Sarah Verified Background CheckRover 101

Fido’s friend while you’re away!

Arlington, MA, 02474

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Sarah was fantastic to work with! She left great updates and made me feel totally comfortable that my dog was in great hands while I was away. Will definitely … (more)"

18. Rebecca Verified Background Check

Dog and animal lover extrodinaire

Woburn, MA, 01801

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Rebecca was fantastic! She was on time for every drop in so my dogs were never in danger of having an accident and more importantly she gave them plenty of lov… (more)"

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19. Stephanie Verified Background Check

Winchester🙋🏻‍♀I'm a resident too

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

About: My name is Stephanie R. I most recently was the supervisor at a local dog kennel. I live in Winchester and am only accepting local pets. I am trai… (more)

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20. Madison M. & Allison Verified Background Check

Double the Love

Winchester, MA, 01890

Drop-In Visits, Dog Walking

"Great dog sitter! Love knowing my fur baby was in good hands while I was at work. Came to my apartment to do a few visits, fed my pup and played with her. Will… (more)"

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.