Pet Sitting & Drop In Visits in Winchester, NH

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

Confirmed Memorial day Availability
1. Tyler

Flexible schedule for your pets!

Brattleboro, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Tyler was quick to respond to my inquiry, and scheduled a “Greet and Meet” to learn about our home and meet the cat. When the time came he was prompt with b... (more)"

Confirmed Memorial day Availability
2. Becca

Experienced Animal Caretaker

Orange, MA, 01364

House Sitting, Drop-In Visits, Dog Walking

22 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. 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)

Confirmed Memorial day Availability
4. 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)

5. Glen

Reliable, Friendly, Honest

Winchester, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

"Glen loves dogs, he has been around dogs for many years, he also knows how they act when they are hungry, need to go out, interacts with them, plays with the... (more)"

Confirmed Memorial day Availability
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)"

7. Noelle

guaranteed two paws up

Keene, NH, 03431

Drop-In Visits, Dog Walking

About: Animals have always been a passion of mine. I have two dogs of my own as well as two cats. I have serveral years of experience fostering rescue pup... (more)

8. Elysse

Dog Lover Excited to Meet Your Pup

01301, Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Elysse once again was a great sitter as she dropped in on our two pups, Tevin and Rye, who have quite a level of energy! She was very communicative and we lo... (more)"

9. 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)

10. Lisa

Flexible Dog Lover

Montague, MA, 01351

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

About: I have been working around animals for over 15 years. I grew up on a farm and have had about every domestic animal possible. I have a passion for a... (more)

Confirmed Memorial day Availability
11. Simone

Experienced Pre-Veterinary student

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

About: Hello, my name is Simone and I'm currently a college student and my hope is to go to veterinary school after I graduate. I have a lot of experience... (more)

12. 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 used to take care of our dog, Ellie, when we were away. She is the best dogsitter we've ever had. Each time Emily took care of her, Ellie would come b... (more)"

13. Lia

Experienced Animal Companion

Shelburne Falls, MA, 01370

House Sitting, Drop-In Visits, Dog Walking

About: Hi, my name is Lia. I am a 30 year old artist. I was born and raised in a rural part of northern NJ where we always had a wide variety of animals... (more)

Confirmed Memorial day Availability
14. Jane

Large, fenced FARM for pets!

WINCHESTER, NH, 03470

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

1 repeat client

"I'm so happy I was able to relax on my vacation and not feel worried about my dog! Jane was so wonderful. Very friendly, professional, accommodating, and com... (more)"

Confirmed Memorial day Availability
15. Bridget

Let me love 'em while you're away!

Vernon, VT, 05354

House Sitting, Drop-In Visits, Dog Walking

"Bridget would be an excellent dog walker. She has been our farm sitter now for many years - horses, cows, chickens, dogs and cat. She is responsible, confide... (more)"

16. Indigo

Sweet, Down to earth, doggy lover!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Indigo is the best. She took the time to let Buddy warm up to her and was very thoughtful to him. She also took lots of pictures. I have found a sitter for... (more)"

17. Samara

Dogs are my #1 favorite

Guilford, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Samara is friendly and kind. And she is definitely an animal lover for sure. My dog is is skittish and timid around new people. Samara immediately had a grea... (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. 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)"

20. Rosemary

Responsible, fun, and active!

Brattleboro, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

About: I have experience taking care of dogs from my childhood golden retriever. We had our golden retriever for 9 years. He was my buddy! I have experien... (more)


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