Pet Sitting & Drop In Visits in Sheffield, MA

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

1. Betsy

Bonus: I'm a wildlife biologist!

Millerton, NY, 12546

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Fantastic! Reliable, trustworthy, strong integrity. Will invite to be Sadie's sitter again for sure. Came home after a long day away, and she had been we... (more)"

Confirmed Holiday Availability
2. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

5 repeat clients

"Kelsey was so sweet to our pets and she was very responsive. Would definitely hire again! (more)"

Confirmed New Years Availability
3. Stephanie

friendly, charismatic, and caring

waterbury, CT, 06704

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ever since I met Stephanie I knew she was a dog walker and a Pet sitter for a few people. She did it on the side to make extra money to pay for school. She's... (more)"

4. Bria

**10% OFF New Clients + Grooming**

Millbrook, NY, 12545

House Sitting, Drop-In Visits, Dog Walking

About: Does your pooch need a play date? Are they bored all day by themselves? Are you going away and don't want to stick them in a kennel for a week at ... (more)

Confirmed Holiday Availability
5. Kelci

An experienced sitter for 11 years!

Pawling, NY, 12564

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Great dog walker! (more)"

Confirmed Holiday Availability
6. Sarah

Dog lover and Caretaker

Riverton, CT, 06065

House Sitting, Drop-In Visits, Dog Walking

"Sarah house sat and took care of our dog and two cats while we were traveling out of the country for 14 days. Our pets seemed to enjoy being with Sarah. She... (more)"

7. Laura

I have a Dob myself

Mt. Tremper, NY, 12457

House Sitting, Drop-In Visits, Dog Walking

"Laura is one of the sweetest, kindest and most trustworthy people I know. She's great with animals and I'd trust her with my own anytime. In fact I have. She... (more)"

8. Kelly

love spending time with dogs!

Great barrington, MA, 01230

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

1 repeat client

About: My history would be that I've grown up with dogs my whole life. There has never not been a dog in my household and if i could spend all of my time ... (more)

9. Kathryn

Mature, loving, compassionate care

Canaan , CT, 06018

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Kathryn Fisher has grown up in a dog loving household. She has had a dog at home every year of her life, most years 2 at a time. Kathryn has shown responsibi... (more)"

Confirmed Holiday Availability
10. Danielle

Large Property- Loving Family

Hillsdale, NY, 12529

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

About: Over 20 years experience. From House sitting pet families, daily walks to at home care, I have done it all. Dogs warm up to me immediately. I can ... (more)

11. Brianna

I will run and take your dog hiking

Stormville, NY, 12582

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

2 repeat clients

"Brianna has been a dream come true for my family and our furry family member. Brianna started with us when we were losing our first dog to old age. Our sweet... (more)"

Confirmed Holiday Availability
12. Heidi

2 for 1 Fur baby Lovers ❤️

Port Ewen, NY, 12466

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

"We are so thankful that we found Heidi. As someone who treats their dogs like their children we were so relaxed and at ease from the moment we met Heidi. W... (more)"

13. Iris

I am a dog whisperer and magnet.

Norfolk, CT, 06058

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Iris always develops a personal relationships with the dogs she takes care of. She treats every dog as she would her own. She is responsible, trust worthy, a... (more)"

14. Amber

Veterinary Trained Dog Lover!

Delaware Avenue, Albany, NY, 12209

House Sitting, Drop-In Visits, Dog Walking

About: I grew up with lots of animals. Before and during college, I worked as a veterinary assistant. After college, I volunteered at the humane society. ... (more)

Confirmed Christmas Availability
15. Sarah

my dog <3's your dog

Downtown, Hartford, CT, 06103

Dog Boarding, Drop-In Visits, Dog Walking

"I have known Sarah since a young age. She has a big heart for animals but dogs especially. I have trusted her on more than one occasion to watch my dog Luna.... (more)"

16. Melissa

Absolutely LOVES dogs!!

New Hartford, CT, 06057

House Sitting, Drop-In Visits, Dog Walking

"Melissa is an amazing dog sitter and "Dog Aunt" as we call her to my puppy, Guille. She has been watching Guille for me while I was on vacation since he was ... (more)"

Confirmed Holiday Availability
17. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

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

17 repeat clients

About: ****Send your pup on vacation while you travel :)*** I offer dog sitting in your home as well as mine and I have discounted doggie walks **** Hell... (more)

Confirmed Holiday Availability
18. Taylor

The animals always come first.

Granville, MA, 01034

Drop-In Visits, Dog Walking

"Taylor is a very smart and caring woman who loves caring for all types of pets. She has a sweet disposition and has a lot of experience that allows her to ca... (more)"

Confirmed Holiday Availability
19. Marcea

48 years Loving Other People's Pets

West Hartford, CT, 06110

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Marcea is a warm, wonderful person; great with both our senior dog and spunky pup! Highly recommend! (more)"


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 Sheffield 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 Sheffield, 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 Sheffield pet sitters and avoid the kennel.