Pet Sitting & Drop In Visits in Windsor, MA

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

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1. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

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

2 repeat clients

"We couldn’t be more pleased! Heather does drop-in visits for us to care for our German Shepherd when we’re away and there’s nothing like being able to leave ... (more)"

2. Carolyn

IT'S ALL ABOUT THE SNUGGLE

Jacksonville, VT, 05363

House Sitting, Drop-In Visits, Dog Walking

"I have known Carolyn for over 40 years. She is one of the most compassionate, attentive animal lovers I have ever met. She genuinely loves all animals and tr... (more)"

Confirmed availability
Memorial day
3. Ashley

Comes with love

Montgomery, MA, 01085

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ashley came back for another drop-in visit while we were out of town for the day. She came right on schedule and even sent us a selfie of her with our dog. T... (more)"

Confirmed availability
Memorial day
4. Alyson

Flexible schedule, love walking

Dalton, MA, 01226

Drop-In Visits, Dog Walking

"Alyson LOVES dogs and loves to hike/walk, she is beyond reliable & trustworthy and I highly recommend her to take care of your beloved pet! (more)"

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5. Sara

Dogs think I'm one of them.

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"I have known Sara for 35 years. She is an extremely reliable and compassionate caregiver to animals. Recently she met my dog, and Garnet (who is usually shy ... (more)"

Confirmed availability
Memorial day
6. Meagan

Difficult Dog? You can trust me!

Turners Falls, MA, 01376

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

2 repeat clients

"Meagan has taken care of our 5 dogs and 2 cats on two separate occasions and I can;t think of anyone better qualified of more trustworthy. Meagan has a a wo... (more)"

Confirmed availability
Memorial day
7. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

7 repeat clients

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

Confirmed availability
Memorial day
8. Angela

Large Yard for Big Play Times!

Shelburne falls, MA, 01370

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

"Our family has know Angela for years. We travel several times a year for at least a week and always ask her to take care of our animals. We have a dog, two ... (more)"

Confirmed availability
Memorial day
9. Bree

Experienced Animal Enthusiast!!!

S Deerfield, MA, 01373

House Sitting, Drop-In Visits, Dog Walking

"I’ve know Bree for over ten years and since then ive found out how much love she has for dogs and other pets as well. Not only does she own dogs and cats but... (more)"

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10. Laura

Service dog trainer & doggo lover

Sunderland, MA, 01375

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I know Laura because she is is a close friend of my daughter. Laura has been to our home on many occasions. Some of the visits included her beloved dog Merli... (more)"

11. Emily

Intuitive Care for High Energy Dogs

Greenfield, MA, 01301

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

4 repeat clients

"Emily came and watched my dog and two cats while I was on a trip and did a wonderful job! She was very flexible, sent me some pictures and updates, and Blue ... (more)"

Confirmed availability
This weekend
12. Kelly

Family of dogs love them like mine

Stephentown, NY, 12168

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

About: Worked fostering dogs for over 20 years and my mom was a vet tech we have always loved our animals like family they bring so much joy to our lives.... (more)

Confirmed availability
Memorial day
13. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Our girl has a home <3 away from home! She is very loved and cared for by Samantha! :) Thank you again for taking her short notice! 5 star & beyond <3 (more)"

Confirmed availability
This weekend
14. Nathan

I'll take your dog to the park

Weststockbridge, MA, 01266

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

About: I love animals I'm kind and friendly I am respectful and responsible. I will keep your dog happy and we will become friends. I've had dogs througho... (more)

15. Emma

A dog depraved college student!

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Emma is a very companionate and fun loving girl. She has a deep love for dogs and is a very great owner of her own dog. She constantly makes sure her dog has... (more)"

16. Taylor

Dog lover with big heart!

Hinsdale, MA, 01235

Drop-In Visits, Dog Walking

"Taylor is a fun and hardworking ray of sunshine. Who better to help you with your family pet than someone who would do anything to make her puppers smile ? R... (more)"

17. 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)"

18. Lauren

Training and care experience!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

"Lauren was prompt and professional, she is an excellent sitter. (more)"

19. Michael

Friendly guy, to both people & dogs

Florence, MA, 01062

House Sitting, Drop-In Visits, Dog Walking

"Such is Michael's love for pups that that is what I call him - Pup! Pup speaks often and lovingly of the pup of his youth, Kasha, a handsome Samoyed with reg... (more)"

20. Brandon

Loving care for your pet

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

About: I have had dogs in my house for the last 15 Year’s. I currently take care of two of my own. I enjoy taking my dogs on hikes on various trails aroun... (more)

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Windsor pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Windsor, MA who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.