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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Kathleen

Always put your best paw forward!

Chester, VT, 05143

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

1 repeat client

About: I live in beautiful Chester, VT. I have spent time with dogs every day of my life and I couldn't ask for anything better. I have been walking and b... (more)

Confirmed Holiday Availability
2. Jennifer

Let Me Love Your Fur Babies

Swanzey , NH, 03446

House Sitting, Drop-In Visits, Dog Walking

"Jennifer was amazing and our puppy had a great time with her!! She was very courteous, understanding and willing to work with us and our puppy. Thanks Jen!! (more)"

3. 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)"

4. Caitlin

Caring and a lover of furry friends

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

"Caitlin is one of the sweetest, most caring people I know. She has a lot of compassion, especially for animals, and has experience dealing with dogs and walk... (more)"

5. Kally

I'm a very responsible individual.

Keene, NH, 03435

Drop-In Visits, Dog Walking

About: I've had dogs my whole life, and have been around them for a while. I have house sat before, and taken care of animals. I'm very friendly with dogs... (more)

Confirmed Holiday Availability
6. Courtney

Love to make the dogs smile!

Richmond, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

About: I have worked with dogs for three years. One year was spent with a dog breeder. Two years were spent with a boarding and daycare facility. I am pet... (more)

7. Danielle

Loving and caring dog enthusiast

worcester, MA, 01606

House Sitting, Drop-In Visits, Dog Walking

About: I have always had an extreme love for dogs and can get along with any dog, big or small. I have raised my own pups and have watched family dogs whi... (more)

8. Dakota

Animal lover studying Vet Med!

Baldwinville, MA, 01436

House Sitting, Drop-In Visits, Dog Walking

"Dakota was wonderful! I had zero worries. She was prompt with answering and I received updates of how my Cali was. She did a wonderful job and kept everythin... (more)"

9. Caitlin

Caring and a lover of furry friends

Keene, NH, 03431

House Sitting, Drop-In Visits, Dog Walking

"Caitlin really loves animals of all kinds. She has a very big heart, and is very good with dogs. She took a dog training class with my dog, Lucy, and has tak... (more)"

10. Danielle

Loving and caring dog enthusiast

worcester, MA, 01606

House Sitting, Drop-In Visits, Dog Walking

About: I have always had an extreme love for dogs and can get along with any dog, big or small. I have raised my own pups and have watched family dogs whi... (more)

Confirmed Holiday Availability
11. Courtney

Love to make the dogs smile!

Richmond, NH, 03470

House Sitting, Drop-In Visits, Dog Walking

"Courtney was great .. My pups were well looked after and taken care off. Courtney took them for walks and played with them. Also kept us up to date and sent ... (more)"

Confirmed Holiday Availability
12. Kathleen

Always put your best paw forward!

Chester, VT, 05143

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

1 repeat client

"Kathleen was wonderful with my dogs. She is so personable and loves dogs. I didn't worry while I was away and she sent me photos of them. I would definitely ... (more)"

Confirmed Holiday Availability
13. Jennifer

Let Me Love Your Fur Babies

Swanzey , NH, 03446

House Sitting, Drop-In Visits, Dog Walking

"Over the past 11 years, I have trusted very few people with caring for my dog. Jennifer is one of the chosen few! Simply because she is amazing! She cares fo... (more)"

14. Mallory

Experienced Pet Sitter at Your Service!

Amherst, MA, 01003

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Like most pet owners, we were very nervous about leaving our girl, Karma, with a stranger. When our usual vacation options were limited, we considered kenne... (more)"

15. Sarah

A Compassionate Dog Whisperer

Fitchburg, MA, 01420

House Sitting

About: I have experience with dogs of all sizes. Positive reinforcement training is my strong point. Mostly I provide companionship, exercise, training, a... (more)

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Learn About Premier

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 free 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.