Pet Sitting in Stockbridge

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
 Easter weekend
1. Kathleen Verified Background CheckRover 101

Berkshires #1 Trusted Pet Sitter ❤️

Becket, MA, 01223

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

"Kathleen is hands down the best dog sitter! We felt so at ease leaving him with her for the day. Sampson had the BEST day and was the happiest pup when we cam… (more)"

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2. Justina Verified Background Check

I treat your pet like family!

Pittsfield, MA, 01201

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

"Every dog I know loves Justina! I work in an office with her and we sure do wish we could have dogs in the office with us. Justina has gone on multiple dog wa… (more)"

3. Rachel Verified Background Check

Your dog’s future best friend

Valatie, NY, 12184

House Sitting, Drop-In Visits, Dog Walking

"We recently started using Rachel as our drop in dog sitter for 30 minute visits when I am out of town for work and my husband is unable to take her to work wit… (more)"

4. K M Verified Background Check

One with your pet

Stephentown, NY, 12168

Drop-In Visits, Dog Walking

"We were lucky to find her! She was prompt and responsive, and very flexible—we contacted her last minute. Easy to communicate with. Dealt with our three dogs w… (more)"

5. Danielle Verified Background Check

Large Property- Loving Family

Hillsdale, NY, 12529

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

"Excellent! I received daily comments as well as pictures. My dog can be very excitable with new people, so it’s difficult to leave her knowing she’s not an ea… (more)"

6. Julia Verified Background CheckRover 101

Love working with animals!

Ghent, NY, 12075

House Sitting, Drop-In Visits, Dog Walking

"Julia did a wonderful job taking care of our dog. She was attentive, detail oriented, and passionate about the care she provided. We also appreciated the pictu… (more)"

Confirmed availability
 Easter weekend
7. Kelly Verified Background Check

Our Home for Your Best Friend

Otis, MA, 01253

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

"My dogs absolutely adore Nabil and Kelly. When we pull into their driveway they squirm with excitement, and when I open the car door, they leap out and run to … (more)"

8. Jeanne Verified Background Check

Country setting, lots of hiking

pittsfield, MA, 01201

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

"Jeanne has cared for my dog Millie many times. She loves going there and playing with Stella (Jeanne's dog). There's a lot of room to play inside and outside.… (more)"

9. Loren Verified Background Check

Fun loving dog mom!

Lee, MA, 01238

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

"Loren was wonderful! She was a super friendly, always available to answer my messages, and gave me daily updates and photos. I felt total peace of mind knowing… (more)"

10. Jessica Verified Background Check

Fun and caring dog sitter

Canaan, NY, 12029

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

"Jessica is a terrific dog sitter! She has such a gentle and caring nature about her and it shows when she interacts with my dog, Oliver. Jessica has taken care… (more)"

11. Megan Verified Background Check

Super caring, loving, animal lover

Pittsfield, MA, 01201

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

"My dogs love Megan! She is a natural dog lover and they run right to her! (more)"

12. Melissa Verified Background Check

Starlight farm: Home away from home

Otis, MA, 01253

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

About: I am an animal lover of 30+ years and a veterinary technician of 11 years. I have experience in wellness care, surgical and emergency hospitals which… (more)

13. Tara Verified Background Check

Your dogs family when family can't

Lee, MA, 01238

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

About: I am a true dog loving mom and family. We rescue boston terriers. Any dog that comes thru our door becomes family. We love to play ball take long wal… (more)

14. Brittany Verified Background Check

Hiking with dogs is my favorite!

Richmond, MA, 01254

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

"I have never met someone who literally fits the perfect mold of a “dog whisperer” until I met Brittany. She has a distinct gift when it comes to working with d… (more)"

15. Bethany Verified Background Check

Experienced dog & cat sitter

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: I grew up in a family that bred and trained dogs. I had my GSD trained to hold his breath, for fun. I’ve worked at doggie daycare and with cat rescue… (more)

16. Ava-Lena Verified Background Check

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

"Very professional and saved me in the last minute! (more)"

17. Monica Verified Background Check

Hello! Welcome to my page:)

Great Barrington, MA, 01230

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

"Monica has been a huge help to me and my family. To taking out my puppy when I’m stuck at work. Or even just spending some time with her if I can’t. She’s resp… (more)"

18. Sofia Verified Background Check

Friendly and Reliable Pet Lover

Hillsdale, NY, 12529

Drop-In Visits, Dog Walking

About: I've taken care of my pets, my friends and family's pet ever since I was young. My mother was a part-time pet sitter and would take me with her to wa… (more)

19. Michael Verified Background Check

Big Animal Lover!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits

About: 29 years of personal and professional experience caring for rescued cats and dogs. Have owned both on and off my entire adult life. Last rescue was a… (more)

20. Kelsey Verified Background CheckRover 101

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

"Kelsey is terrific! She loves dogs and my dog loved her. She saved me at the last minute and even came over earlier in the day so we could meet her. We hope sh… (more)"


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