Pet Sitting & Drop In Visits in Winchendon, MA

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
Memorial day
1. Krissy

The Best Care For Your Best Friend!

Ashburnham, MA, 01430

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Krissy is an awesome compassionate pet person who made me feel comfortable instantly with my Frankie! (more)"

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2. Brittney

Available weekends, love hikes!

Winchendon, MA, 01475

Dog Boarding, Drop-In Visits, Dog Walking

"I met Brittney a year ago when we ran into each other bringing our sweet pups outside. Since then, Brittney and I have stayed in touch and on multiple occasi... (more)"

3. Heather

The Mary Poppins of Pooches

Ashburnham, MA, 01430

House Sitting, Drop-In Visits, Dog Walking

"I have used Heather in the past to watch my 5 pugs! She was extremely attentive to what we wanted and what our crew needed. She has a loving passion for pets... (more)"

4. Susan

Dog & Cat sitter

Winchendon, MA, 01475

Drop-In Visits, Dog Walking

3 repeat clients

"Thank you so much Susie for a great job!! She was very timely and commutation was excellent!! Tucker enjoyed his two drop-in visits. Will definitely hire aga... (more)"

5. Kim

Experienced Pet Care Professional

Winchendon, MA, 01475

Drop-In Visits, Dog Walking

About: Hi, my name is Kim. I am a "Mom" to 4 boys, 2 dogs, 4 cats, 3 bunnies, and 2 birds. I have experience in caring for a variety of pets for over 20 y... (more)

6. Hailey

Will pamper your lovely pup!

Fitchburg, MA, 01420

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

About: Hi! My name is Hailey and have had experience with dogs (and other animals) almost my whole life. My family got our first dog when I was 7 years ol... (more)

Confirmed availability
Memorial day
7. Meaghan

The best care for your best friend

Phillipston, MA, 01331

House Sitting, Drop-In Visits, Dog Walking

About: Hi, I am currently a vet tech student and I work at a pet store and kennel, which gives me experience and knowledge with a large range of animals ... (more)

8. Celeste

I’ll run with your dog

Fitchburg, MA, 01420

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

About: Hello, l have had animals my whole life. From Boxers to chihuahuas!! lve even had cats and birds. Animals are so easy-going to me and l love worki... (more)

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9. Nancy

Animal lover seeking new clients.

Hubbardston, MA, 01452

Drop-In Visits, Dog Walking

3 repeat clients

"Nancy is a dog whisperer. My dogs lover her the minute they met her. (more)"

10. Alexandra

Flexible hours & can do overnights

Hubbardston, MA, 01452

House Sitting, Drop-In Visits, Dog Walking

"Alexandra is a true lover of animals. She treats each and every one as if it was her own. She is reliable and most important, the animals love her! (more)"

11. Carrie

I ran my own pet are business for 8

athol, MA, 01331

Dog Boarding, House Sitting, Drop-In Visits

About: I have taken care of dogs and other animals for years i am a professional. I love and respect animals and would love tbe opportunity to provide gr... (more)

12. Lana

Will care for your dog like my own

Gardner, MA, 01440

House Sitting, Drop-In Visits, Dog Walking

"Lana is a great sitter, she's very friendly and open to anything. She provides great service and will provide for your dog however necessary! No complaints f... (more)"

13. Thomas

Home full-time, fenced yard

Westminster, MA, 01473

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

About: Dog owner and animal lover - I have always struggled to find people to care for our own dog like family -let me be that person for you. I will be y... (more)

14. David

Flexible hours, love all dog breeds

Gardner, MA, 01440

Drop-In Visits, Dog Walking

About: Much like a dog, I am loyal, energetic, and dependable. I've been lucky enough to have owned and cared for dogs since I was a kid so I have a lot o... (more)

15. Chelsea

Walking, running, hiking, with pups

Ashburnham, MA, 01430

Drop-In Visits, Dog Walking

"Chelsea is one of the most loving dog owners/lovers I’ve known. She’s tender and kind and not afraid to be dirty. She loves running and being active, heaven... (more)"

16. Amber

Home full time, long walks

fitchburg, MA, 01420

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

About: Hello My name is Amber I have many years of experience with animals. Taking care of and being around dogs and all other animals is a strong loving ... (more)

17. Maranda

A dog lover of all breeds!

Fitchburg , NH, 03071

Drop-In Visits, Dog Walking

About: I'm an avid dog lover all all breeds. I have more than ten years of experience with pet sitting, waking, and feeding. I have two dogs of my own tha... (more)

18. Dakota

Animal lover studying Vet Med!

Baldwinville, MA, 01436

Drop-In Visits, Dog Walking

"We could not have been happier with the care my dogs got while we went camping! Dakota was great and even tidied up while we were gone! Definitely will be co... (more)"

19. Ashley

Ashley.21. 5 years experience :)

Templeton, MA, 01468

House Sitting, Drop-In Visits, Dog Walking

About: I currently work at a kennel in Orange, Ma. I have five years experience boarding, babysitting, walking, and administering medication to dogs as we... (more)

20. Samantha

Special educator - love animals!

Gardner, MA, 01440

House Sitting, Drop-In Visits, Dog Walking

About: I am a full time special education teacher that loves spending time with my dog and two cats! I have experience with dog training and puppy care as... (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 Winchendon 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 Winchendon, 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 Winchendon pet sitters and avoid the kennel.