Pet Sitting & Drop In Visits in Stockbridge, 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. Sara

Dependable and Active!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits

"Sara came to our resort unit on Sunday before the sitting day we needed which was Thursday. There was some confusion as to the times she would be available.... (more)"

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)"

3. Annemarie

Daragan's walks/expert dog care

Sixteen Acres, Springfield, MA, 01118

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

About: I am a dog breeder and have bread Gold Retrievers for five years. In addition, I have trained aggressive dogs with excerise, trust and by working ... (more)

4. Shane

I'm the guy to help with your dog

dalton, MA, 01226

House Sitting, Drop-In Visits, Dog Walking

About: I have had dogs my whole life: large, medium and currently two small dogs, who I love a lot. I enjoy spending time with dogs: playing, relaxing...... (more)

5. Kristin

Home full time, 4 acres yard space

Goshen, MA, 01032

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

2 repeat clients

About: Have owned dogs for over 20 years, pet sit for friends, family, and neighbors. I am over cautious and protective when it comes to animals, I'm also... (more)

6. Jennifer

happy dogs need hugs

Valatie, NY, 12184

House Sitting, Drop-In Visits, Dog Walking

"Jennifer is a conscientious and loving caregiver. She has a calm and happy demeanor that your pets will pick up on and adore. I can't recommend her highly en... (more)"

7. 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)

Confirmed President's Day Availability
8. 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)"

9. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

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

1 repeat client

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

10. 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)

11. Meredith

Petting, play, or pooping? Got it!

Pittsfield, MA, 01201

Drop-In Visits, Dog Walking

"We love Meredith! And so do our puppies. She was so thoughtful with both our pets and our home while we were away. She is incredibly kind and reliable, an... (more)"

12. Shelby

Dogs are my absolute passion

New Milford, CT, 06776

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

1 repeat client

"Shelby is an absolute gem. I started working two jobs and unfortunately wasn't able to give my little fur baby the full attention she deserved, so I called u... (more)"

13. 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)"

14. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

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

19 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)

15. Ocean

Reiki Practicioner, Peaceful Energy

Hurley, NY, 12443

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

"Ocean is the best ever with pets! He provided services to my Mini Schnauzer Sanford. Sanford was a much older pup of 18 years old when they met. Sanford t... (more)"

16. Mattie

Fun and friendly dog lover

Lee, MA, 01238

Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Mattie is amazing with animals! She can care for all sorts of different reptiles as well as dogs and cats. I would definitely recommend Mattie for pet sittin... (more)"

17. 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)"

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)"

19. 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)

20. Erin

Best Care for Your Best Friend!

West Stockbridge, MA, 01266

House Sitting, Drop-In Visits, Dog Walking

"Erin is fantastic with our dogs. She is very responsible and caring. We have no hesitation leaving our dogs in her care and highly recommend her. (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.