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 Holiday Availability
1. Nicole

Personalized pet pampering

Greenville, NH, 03048

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Nicole is very friendly, reliable, and so good with our dog! She kept us up to date each visit, and we were very happy with our choice to hire her. I am so g... (more)"

Confirmed Holiday Availability
2. Rebecca

Experienced Animal Caretaker

Orange, MA, 01364

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Rebecca was awesome providing drop-in visits for my dog and cat while I was away for a long weekend. She took pictures throughout her visits to give me a sta... (more)"

3. Susan

Dog & Cat sitter

Winchendon, MA, 01475

Drop-In Visits, Doggy Day Care, Dog Walking

2 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)"

4. Suzanne

Active and responsible dog lover

Lunenburg, MA, 01462

House Sitting, Drop-In Visits, Dog Walking

"Suzanne was great with Petey! Suzanne did a meet and greet and went over everything regarding Petey. She did two drop-ins for us. One in the evening for feed... (more)"

Confirmed Holiday Availability
5. Desiree

❤️ dogs, snuggles, and outdoors!

Gardner, MA, 01440

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

1 repeat client

"Desiree has been an all-star dog lover from the beginning. In fact, she's a grade-A lover of all pets and has that special aura about her that every dog I've... (more)"

6. Judith

A home away from home

Leominster, MA, 01453

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

1 repeat client

"Judy has been an amazing care taker for our 5 year old puggle, Ziggy. When he is with Judy I have zero concerns as I know he is happy and safe. Ziggy loves s... (more)"

7. Drew

Fun, animal loving, pack leader

Leominster , MA, 01453

Drop-In Visits, Dog Walking

2 repeat clients

"Drew was able to accommodate a very last minute request, made sure our puppy was well taken care of, and sent us text updates to let us know how things were ... (more)"

8. 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)"

9. Erica

Monadnock Dog Care

Fitzwilliam, NH, 03447

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"Erica was great! It was great to be able to keep our dog at home while we were gone. Erica made sure to send updates which we really appreciated! (more)"

10. 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)

Confirmed New Years Availability
11. Miranda

Pets are family too!

Temple, NH, 03084

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Miranda is a great pet sitter. While gone on vacation for 2 weeks I had absolute peace of mind . She took wonderful care of my pup. Milli loves her and I'm s... (more)"

Confirmed New Years Availability
12. Hillary

Will love and care for your dog

Fitchburg, MA, 01420

House Sitting, Drop-In Visits, Dog Walking

"Hillary was great at watching my service dog Ziva. I am very over-protective of her and almost never let her out of my sight. I can count the number of peopl... (more)"

13. Kristen

Stay-At-Home Mom With Alot of Time!

Ashburnham, MA, 01430

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kristen was extremely caring with our bears (dogs) while we away for 16 days. She worked and coordinated with another pet sitter so that we could have full... (more)"

14. Courtney

I'll exercise with your dog!

Leominster, MA, 01453

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

"Courtney sat and walked my dog this past week, she did great! Chuck was all tired out by the time I got home, must have had a great day! (more)"

15. Theresa

Dogs think I'm one of them

Lunenburg, MA, 01462

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

2 repeat clients

"Theresa has been great. Gordon is not well socialized and very nervous around new people. He warmed right up to Theresa. (more)"

16. Gina

I love them like they are my own!

Fitchburg, MA, 01420

Drop-In Visits, Dog Walking

About: I've been in veterinary medicine since I was a child, volunteering at cat shelters and animal hospitals until I was old enough to work there. I was... (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)

Confirmed Holiday Availability
18. 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)

19. Dakota

Animal lover studying Vet Med!

Baldwinville, MA, 01436

House Sitting, 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)"

20. Sierra

Experienced Pet Caretaker & Healer

Peterborough, NH, 03458

Drop-In Visits, Dog Walking

"Sierra watches and walks my dog ziggy. He is extremely energetic and alittle aggressive at times. Sierra is such a calming presence for him. Her immediate to... (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.