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.

Available this weekend
1. Becca

Experienced Animal Caretaker

Orange, MA, 01364

House Sitting, Drop-In Visits, Dog Walking

"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)"

2. Tyler

Flexible schedule for your pets!

Brattleboro, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

"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)"

3. Meagan

Difficult Dog? You can trust me!

Turners Falls, MA, 01376

House Sitting, Drop-In Visits, Dog Walking

"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)"

Available this weekend
4. Amanda

Responsible and Reliable

Swanzey, NH, 03446

Drop-In Visits, Dog Walking

"Amanda would make a great pet sitter. She has years of experience caring for many dogs and cats. She has two dogs of her own, one who is advanced in age, the... (more)"

5. Elysse

Dog Lover Excited to Meet Your Pup

01301, Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

"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)"

6. 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)"

7. Simone

Experienced Pre-Veterinary student

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

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)

8. 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)

9. Emily

Intuitive Care for High Energy Dogs

Greenfield, MA, 01301

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

"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)"

Available this weekend
10. Cassie

A house is not a home without a dog

Keene, NH, 03431

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

"Cassie is amazing with my dog Bo! I was very worried about leaving him in someone else’s hands, but has something about her that really clicks. She is calm a... (more)"

11. Jane

Very experience pet-sitter!

WINCHESTER, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

"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)"

12. Samara

Dogs are my #1 favorite

Guilford, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

"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)"

13. 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)

14. 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)

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

"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. Hailey

Great w/ dogs & flexible schedule

West Brattleboro, VT, 05301

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

About: I love all shapes, sizes, and ages of dogs. I grew up with a sweet Australian Shepard rescue and did all of the training for him after we brought h... (more)

18. Grace

Dogs are my best friends!

Keene, NH, 03431

Drop-In Visits, Dog Walking

"Grace has had dogs her entire life and is a true dog lover. She has a good sense for what a dog needs and can connect with dogs to safely give them the care... (more)"

19. Joe

I will do whatever it takes!

Guilford, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

About: I have experienced with dog for 5+ years. I have done overnight shifts at a family farm looking after dogs, cleaning up after them, feeding them ev... (more)

20. Jennifer

Reliable, Responsible & Experienced

Erving, MA, 01344

House Sitting, Drop-In Visits, Dog Walking

"I have known Jennifer for over thirty years. She is a wonderful and caring woman with whom I would fully trust with my own animals. From dogs to cats to fish... (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.