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Pet Sitting & Drop In Visits in Chester, NY

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

Confirmed availability
4th of July
1. Lisa

Home full time!

Florida, NY, 10921

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

"Lisa was wonderful and friendly. We were able to have a night away for our anniversary without worrying. Lisa followed directions, sent updates and was all a... (more)"

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2. Jennifer

Ready to walk your dog

Chester, NY, 10918

Drop-In Visits, Dog Walking

"Jennifer is a very dedicated woman.. she has been around many animals and they seem to be drawn to her. Jennifer always has a great personality and so frie... (more)"

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3. Suzanne

Caring, dependable, Licensed Tech!

Monroe, NY, 10950

Drop-In Visits, Dog Walking

"Suzanne took great care of our cats. She sent us a lot of pictures, kept us up-to-date on how they were doing, and was very responsive to all our questions a... (more)"

4. Jessica

Home away from home!

Monroe, NY, 10950

Drop-In Visits, Doggy Day Care, Dog Walking

"Jessica is an experienced dog owner. She not only takes excellent care of her dog, but she also helps with an animal rescue organization by fostering and tra... (more)"

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5. Julia

Will meet the needs of your pets!

Chester, NY, 10918

Dog Boarding, Drop-In Visits, Dog Walking

"Julia was great she was punctual and very patient with Daisy and Daisy is not the easiest dog to get to know. She is a 13 year old doberman and set in her wa... (more)"

Confirmed availability
This weekend
6. Liz

Loving Care when you're not there

Chester, NY, 10918

Drop-In Visits, Dog Walking

"Liz is a great sitter. She is great with Bella, very punctual and sent me text updates with pictures each visit. Definitely recommend her! (more)"

7. Caitlyn

Home-full time

Monroe, NY, 10950

Drop-In Visits, Dog Walking

About: I have been a dog owner for 10+ years. I have my own dog and am training him to be a service animal. I love animals and playing with them. I love s... (more)

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8. Jackie

I’d love to hang out with your dog!

Washingtonville, NY, 10992

Drop-In Visits

About: My parents got their first dog, a boxer, 12 years ago and I’ve cared for him on and off all of that time. He is a senior dog now who has trouble wa... (more)

Confirmed availability
4th of July
9. Jane

Waggles Home Away from Home

Chester, NY, 10918

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

About: We can't wait to take care of your dog! We are an active couple with flexible schedules and one of us will be around most of the time to keep your... (more)

10. Matthew

Home full time from college

Chester, NY, 10918

House Sitting, Drop-In Visits, Dog Walking

About: I am a college kid home from school for winter break, I have had, and been around dogs since I could crawl. Have never had a problem with any dogs ... (more)

Confirmed availability
4th of July
11. Claudette

Young & Energetic Animal Lover

Monroe, NY, 10950

House Sitting, Drop-In Visits, Dog Walking

"Claudette is one of the most trustworthy people I've ever met and she's had dogs her whole life so she knows what she's doing! She is kind and responsible an... (more)"

Confirmed availability
4th of July
12. James

/Homemade treats/run/play/snuggles/

Washingtonville, NY, 10992

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

"James has cared for my pup (Colby) multiple times over the last two years. For a few hours during the day, sometimes for a quick walk and other times for ex... (more)"

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13. Tom

I've always been a dog-person! :)

Monroe, NY, 10950

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

"Tom is such an amazing and responsible caregiver. Our husky, Jack, really took to him right away. He is very loving and hands-on. He played with Jack and was... (more)"

14. Randi

Dog buddy right here :)

Goshen, NY, 10924

House Sitting, Drop-In Visits, Dog Walking

About: I have been the owner of 2 great dogs since May 2015, a lab hound and a chihuahua mix. Love going outside and playing, walking, enjoying the fresh... (more)

Confirmed availability
4th of July
15. Andrew

I'll care for your dog like my own!

Goshen, NY, 10924

House Sitting, Drop-In Visits, Dog Walking

"Andrew has a passion for animals and has considerable experience walking and caring for dogs. He has worked for a rescue for several years, in particular the... (more)"

16. Kelly

Your dog nose best. (:

Goshen, NY, 10924

House Sitting, Drop-In Visits, Dog Walking

"Kelly has taken care of my two big fluffy Samoyeds for years. She had the most bubbly, warm personality and does everything she can to take care of absolutel... (more)"

17. Mikayla

Large Yard, walk, run and play

Goshen, NY, 10924

Dog Boarding, Drop-In Visits, Dog Walking

"Mikayla watched my dog Oliver last summer for 10 days and she did a great job. Walking, feeding and playing outdoors with him. She is used to cats and dog... (more)"

18. Marilyn

Professional & Loving Care

monroe, NY, 10950

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

"Great service thank you for everything you did for Spot and Brownie they loved you and their nice long walk. Your patience was great with how hyper the two d... (more)"

19. Nicole

I’ll love your dog!

Chester, NY, 10918

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

"Nicole is the sweetest ! As soon as I met her I felt comfortable leaving my little dog, Hercules, with her. She not only had scheduled walks with him but als... (more)"

Confirmed availability
4th of July
20. Sarah

I want my career to do with dogs

Florida, NY, 10921

House Sitting, Drop-In Visits

About: When I was in high school I took the animal science class at Boces CTech and owners would drop off their dogs and we would have to walk them, train... (more)


Rover.com is the simple, savvy way to find and book Chester 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 Chester. 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.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.