Pet Sitting in Winchester

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

1. Celia Verified Background Check

Lots of love, care, and play time

Swanzey, NH, 03446

House Sitting, Drop-In Visits, Dog Walking

"Celia was great in last minute scheduling for walking my dog. She did a great job, followed all my directions, and I came home to very happy and contented an... (more)"

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2. Becca Verified Background CheckRover 101

Experienced Animal Caretaker

Orange, MA, 01364

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

"We have a total of four dogs, three of which are under a year old, and Becca proved herself more than capable of dealing with all of them. In addition, two o... (more)"

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3. Tyler Verified Background Check

Flexible schedule for your pets!

Brattleboro, VT, 05301

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

"I was delighted to arrive home after my trip and find Lady playing happily outside with Tyler. Tyler took very good care of Lady and my home while I was awa... (more)"

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4. Samara Verified Background Check

Dogs are my #1 favorite

Guilford, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

"Samara was wonderful! We had a friend cancel on watching our pets just a day before we left for our 10 day trip, but luckily we were able to find Samara who ... (more)"

5. Cassie Verified Background Check

A house is not a home without a dog

Keene, NH, 03431

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

"Cassie was reliable and on time taking care of my pups! Took great care of them! I’d highly recommend her! (more)"

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6. Nichole Verified Background Check

I love animals!

Orange, MA, 01364

House Sitting, Drop-In Visits, Dog Walking

"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 a... (more)"

7. Jennifer Verified Background Check

Reliable, Responsible & Experienced

Erving, MA, 01344

House Sitting, Drop-In Visits, Dog Walking

"I’m so glad I could rely on Jennifer all week to come give my dog some playtime and water/pee breaks! She will definitely be added to my list of dependable a... (more)"

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8. Rosemary Verified Background Check

Responsible, fun, and active!

Brattleboro, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

"Rose is an amazing dog sitter!! She goes above and beyond to ensure that Sophie (my dog) is taken care of and get the exercise that she needs. Sophie loves her. (more)"

9. Courtney Verified Background Check

Adventurer ISO hairy friends

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

"courtney was amazing!! she dropped in to check on my dog and cat while i was visiting family out of state. i was so grateful bc she noticed my cat got out on... (more)"

10. Taylor Verified Background Check

Professional Pet Care

Vernon, VT, 05354

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

About: I have experience with a wide range of animals, pretty much everything from horses to mice! I have worked at my local humane society for about a ye... (more)

Confirmed availability
Memorial day
11. Dave Verified Background CheckRover 101

caring dog walker and cat sitter

Keene, NH, 03431

Drop-In Visits, Dog Walking

About: I am an animal lover and life long pet owner of cats and dogs. I am looking to walk dogs and cat sit at owners home. I have volunteered at several ... (more)

12. Glen Verified Background CheckRover 101

Reliable, Friendly, Honest

Winchester, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

"Glen loves dogs, he has been around dogs for many years, he also knows how they act when they are hungry, need to go out, interacts with them, plays with the... (more)"

13. Rachel Verified Background Check

I’ll hike and love your dog!

Athol, MA, 01331

Drop-In Visits, Doggy Day Care, Dog Walking

"I have known Rachel personally for the better part of my life. Not only has she been an avid animal lover, in particular she has always been fond of dogs. Th... (more)"

14. Noelle Verified Background Check

guaranteed two paws up

Keene, NH, 03431

Drop-In Visits, Dog Walking

About: Animals have always been a passion of mine. I have two dogs of my own as well as two cats. I have serveral years of experience fostering rescue pup... (more)

15. Kayla Verified Background Check

I'll take your dog on a run!

Athol, MA, 01331

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I am a college student! I go to college around Newton, Mass. I have been around dogs my whole life and I love them so much! I am good with all diff... (more)

16. Amanda Verified Background Check

Responsible and Reliable

Swanzey, NH, 03446

Drop-In Visits, Dog Walking

"Amanda would make a great pet sitter. She has years of experience caring for many dogs and cats. She has two dogs of her own, one who is advanced in age, the... (more)"

Confirmed availability
Memorial day
17. Jane Verified Background Check

Very experience pet-sitter!

WINCHESTER, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

"I'm so happy I was able to relax on my vacation and not feel worried about my dog! Jane was so wonderful. Very friendly, professional, accommodating, and com... (more)"

18. Anna Verified Background Check

Just your average animal lover

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

About: Hello my name is Anna, I have been working with dogs since a young age and have always taken an interest in the tranning. I have attended a great d... (more)

19. Kara Verified Background Check

Dedicated to tiring out your pup!

Vernon, VT, 05354

House Sitting, Drop-In Visits, Dog Walking

About: I am dedicated to making sure your dogs get the attention, playtime, and exercise they need while you're away at work! I know that dogs can become ... (more)

20. Taylor Verified Background Check

Will exercise dog frequently

Keene, NH, 03431

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

About: I am an animal lover to my core. Ever since I was a little kid, dogs have been a part of my life. I have had several golden retrievers in my life... (more)


Rover.com is the simple, savvy way to find and book Winchester drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Winchester. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.