Pet Sitting & Drop In Visits in Southold, NY

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

1. Sara

I’ll run and hike with your dog!

Old Saybrook, CT, 06475

House Sitting, Drop-In Visits, Dog Walking

About: I have loved dogs ever since I was a kid and my family has had a black lab mix named Rowland for 6 years! Whenever I am home on the weekend or have... (more)

2. Jen

VanaStay Pet Sitting

Cutchogue, NY, 11935

House Sitting, Drop-In Visits

"Jen was amazing from the start. She quickly responded to any message I sent Her passion for her job and the seriousness which she approaches it made us feel... (more)"

3. Meredith

Energetic, fun and dependable

East Hampton, NY, 11937

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

6 repeat clients

"Yes, FINALLY! A sitter I can count on in the hamptons!!! Meredith was amazing. She was very responsive via text, sent lots of pictures and updates and even b... (more)"

4. Kaitlyn

Your dog's newest human friend

Flanders, NY, 11901

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Kaitlyn is the perfect person for Rover! She is a very smart reliable graduate student who loves dogs, of all ages and breeds. She looked after my dog and ca... (more)"

5. Chandler

Lifelong Dog Lover!

Clinton, CT, 06413

House Sitting, Drop-In Visits, Dog Walking

"I met Chandler through our mutual place of work, and she’s become an absolute lifesaver for my husband and I who travel seeing family and friends around the ... (more)"

Confirmed President's Day Availability
6. Maria

Maria's Happy Tails boarding

Sag Harbor, NY, 11963

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

6 repeat clients

About: I'm a long time volunteer with Friends of the Homeless Animals and PAWS (Pioneers for Animal Society) and I have three rescue dogs of my own. I lo... (more)

7. Kelly

Licensed Vet Tech

Mattituck, NY, 11952

Drop-In Visits, Dog Walking

1 repeat client

"Kelly did an excellent job and was great with the cats. (more)"

8. Kelsey

Love long walks on the beach!

Madison, CT, 06443

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

"Kelsey did an amazing job looking after my black lab puppy, Ava. Kelsey came in everyday to walk and play with Ava. I could tell by how tired Ava was when I ... (more)"

9. Elizabeth

Dog Mom 30+ years, Give Lots of TLC

Southold, NY, 11971

House Sitting, Drop-In Visits, Dog Walking

"Elizabeth and Michael are the best. They take such good care of our two dogs. They always give me updates with every visit and give Jasmine and Lola so much ... (more)"

10. Marissa

Gives walks on the beach

Southold, NY, 11971

House Sitting, Drop-In Visits, Dog Walking

About: Hi my name is Marissa! I'm a part time college student and a part time animal enthusiast! As a child, I was lucky to have grown up with pets of all... (more)

11. Ariel

Extremely trustworthy pet sitter!

Old Saybrook, CT, 06475

House Sitting, Drop-In Visits, Dog Walking

About: Hello, my name is Ariel and I am 22 years old. I live in Old Saybrook but stay at my boyfriends house sometimes in Wethersfield, so I am flexible i... (more)

Confirmed President's Day Availability
12. Heather

Loving, trustworthy & reliable

Watermill, NY, 11976

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

1 repeat client

"Heather was responsive and kind to my dog. Her follow up was terrific and I would certainly use her again (more)"

13. Veronica

Animal Lover Available!!!

Riverhead , NY, 11901

Drop-In Visits, Dog Walking

2 repeat clients

"The cats were healthy and happy when I returned. Veronica did an excellent job. (more)"

14. Katrina

Will Love And Care For Your Dog

Sag Harbor, NY, 11963

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

About: I have plenty of years of caring for pets, especially dogs. I used to have a lot of animals in my home growing up, as they provided a sense of resp... (more)

15. Stephanie

Currently a veterinary assistant

OLD SAYBROOK, CT, 06475

House Sitting, Drop-In Visits, Dog Walking

About: Have worked as a veterinary technician for over 3 years, currently working as an assisitant working my way up the scale to be a tech! Worked in Ari... (more)

16. Adelle

Flexible schedule and energetic

Riverhead, NY, 11901

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

About: I am a friendly, warm, dog-loving human who has had dogs all my life. I treat my dogs like family. I am a marine biology PhD student at Stony Brook... (more)

17. roger

Dog Lovers/Fosters & dog portraits

Southampton, NY, 11968

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

3 repeat clients

About: Amy and I work both from home so we have plenty of time to take very good care of dogs, go for walks on the bay beach 5 minutes away. We fostered m... (more)

18. Cassie

Animals are my life

Westbrook, CT, 06498

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

About: Hi, my name is Cassie : ) I live in Westbrook and I currently work at a doggy daycare facility. I am also working on getting my degree as a Veterin... (more)

19. Damaris

Lover of dogs & cats!

Westbrook, CT, 06498

Drop-In Visits, Dog Walking

About: I have had either a dog, cat or both for over 25 years now. My (pets) are Not pets at all, they are my Babies and I treat them as such. I look at a... (more)

20. Alexa

Dog lover. Responsible.

East Hampton, NY, 11937

Drop-In Visits, Dog Walking

About: I really enjoy working with dogs. I took care of a Golden Retriever for about 4 years. I am a hard working person and very responsible. I worked fo... (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 Southold 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 Southold, NY, 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 Southold pet sitters and avoid the kennel.