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.

1. 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)"

2. Tyler

Flexible schedule for your pets!

Brattleboro, VT, 05301

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

2 repeat clients

"I was delighted to arrive home after my trip and find Lady playing happily outside with Tyler. Tyler took very good care of Lady and my home while I was awa... (more)"

3. Olivia

Dogs are not pets there family

worcester, MA, 01609

House Sitting, Drop-In Visits, Dog Walking

"Olivia has a passion and a huge heart for animals! She's super knowledgeable on many breeds, she's patient with my dogs, and understands my dogs are differen... (more)"

4. Joanna

Long term dog mom!

Auburn, MA, 01501

House Sitting, Drop-In Visits, Dog Walking

"Joanna took care of our house and two pets (including managing medications) for us while we were away for a week. She's super responsible, and we were able t... (more)"

5. 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)"

6. Emily

Fun, friendly, fur loving!

South Newfane, VT, 05351

House Sitting, Drop-In Visits

1 repeat client

"Emily has watched our high maintenance, 16 year old Miniature Pinscher for quite a few years now. We have absolutely no worries when Emily is staying at our... (more)"

Confirmed Holiday Availability
7. Jane

Large, fenced FARM for pets!

WINCHESTER, NH, 03470

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

About: Hubby and I are very experienced pet owners. We are in our 50's, semi-retired and have a small farm with sheep, chickens, a 5 y/o male choc lab (P... (more)

8. 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)"

9. Molley

Exercise and Fun from your Own Home

Townshend, VT, 05353

House Sitting, Drop-In Visits, Dog Walking

About: Hello there! My name is Molley :) Growing up here in Southern, VT I have always been around dogs, grew up with them and have been in the pet sitti... (more)

10. Greer

Dog lover born and raised in VT

Putney, VT, 05346

Drop-In Visits

1 repeat client

"Greer has been around dogs since she was born. She is a very responsible young woman who would provide loving care to any beloved pet. (more)"

11. Indigo

Sweet, Down to earth, doggy lover!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Indigo is the most caring person you'll ever meet. Her love for animals is inspirational and should be shared. I would trust not only with my dog but with my... (more)"

12. Tim

Reliable Animal Lover Ready To Help!

Keene, NH, 03431

House Sitting, Drop-In Visits

3 repeat clients

"Tim is the best dog/pet sitter & house sitter. He even cleans! Takes super great care of our pets and even posted pictures for us on Facebook while we were ... (more)"

13. Jennifer

Reliable,trustworthy,in-home sitter

Walpole, NH, 03608

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

1 repeat client

"I recommend Jennifer for pet sitting. She did a wonderful job with my Sammy Dawgs (more)"

14. Heather

Home full-time - Ready to play

Lake Pleasant, MA, 01347

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

About: I love dogs and taking care of them no matter the size. I am available 7 days a week any time of day and will be available to come to your home and... (more)

Confirmed Holiday Availability
15. Kathleen

Experienced dog sitter + hiker :)

Chester, VT, 05143

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

4 repeat clients

About: ​Hello! My name is Kathleen. I believe all dogs are angels. They mean the world to me, all animals truly do. I have been house/pet sitting for 6 ye... (more)

16. Georgia

College Student-Flexible Schedule

Keene, NH, 03431

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

"Ever since Georgia was a little girl, she has had an amazing way with animals. Her sweet, calm demeanor makes pets instantly relaxed and at ease. She is so p... (more)"

17. Mandy

Vet Tech of 10 years, dog lover

Bolton, MA, 01740

Drop-In Visits, Dog Walking

2 repeat clients

"Amanda has had a passion for pets from a very young age. With extensive training from animal hospitals, veterinary clinics and pet adoption organizations whe... (more)"

18. 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)"

19. 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)

20. Jennifer

Dog trainer w/customizable options

Woodford, VT, 05201

House Sitting, Drop-In Visits, Dog Walking

About: I've worked in several kennels over the past 7 years and worked behind the scenes at a veterinary hospital. For the past 3 1/2 years I worked as a ... (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.