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House Sitting in Southold

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability
 Christmas and New Year
1. Kaitlyn Verified Enhanced Background CheckRover 101

Never a dull moment with me around!

Clinton, CT, 06413

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

"Kaitlyn is wonderful. She took the time to come over a few times before we left to meet and get to know Moxie (who is wary of strangers), and Moxie loves her! … (more)"

2. Kylie Verified Background Check

Pet lover house/pet sitter

Clinton, CT, 06413

House Sitting, Drop-In Visits, Dog Walking

"Kylie has been watching my two dogs for forever and they get so excited every time they see her. She is very responsible and always follows through with her co… (more)"

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3. Shannon Verified Enhanced Background Check

Active and doting pet lover!

Guilford, CT, 06437

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

"We were very unsure of what we were going to do with our fur-baby CHARLIE (feline) during our travels, after my Uncle moved to Florida. Charlie has some health… (more)"

Confirmed availability
 Christmas and New Year
4. Maria Verified Background Check

Maria's Happy Tails boarding

Sag Harbor, NY, 11963

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

"maria was great. professional, personable and took great care of our pup. i’d definitely hire her again. (more)"

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5. Sarah Verified Background Check

Dog lover - love to go on walks!

Cutchogue, NY, 11935

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

"Sarah has been taking excellent care of our dog Yogi for a number of years, and I enthusiastically recommend her pet sitting and walking services! Leaving our … (more)"

Confirmed availability
 Christmas and New Year
6. Sarah Verified Enhanced Background CheckRover 101

Belly rubs and head scratches!

East hampton, NY, 11937

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

"We were in a bind, had already left the island for a trip and our sitter fell through. I had to select a sitter Rover from my phone app! I messaged 2 or 3 and … (more)"

7. Brittney Verified Background Check

Give your dog a workout!

Quogue, NY, 11942

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

About: Hello my name is Brittney! I am a grad student and currently available most weekday and all day on weekends. I love being a dog walker because it giv… (more)

8. Lisa Verified Background CheckRover 101

Three Leashes, LLC

Greenport, NY, 11944

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

"Talulah and Gretta, our two Great Danes, absolutely love Lisa! She walks them daily and they are always happy and exercised when we get home from work. Lisa ha… (more)"

9. Brian Verified Background Check

I can be your dog walker baby!

East Hampton, NY, 11937

House Sitting, Drop-In Visits, Dog Walking

"I met Brian back in 2008 when he began attending my yoga classes in St. Thomas, USVI. We became acquainted and then later, friends. He often took care of my Da… (more)"

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10. Jesse Verified Background Check

I have a Friendly 3 year old dog

Riverhead, NY, 11901

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

"Jesse is very responsible young man. This is the first time I have ever left my dogs with a sitter. We cruised for a week and I have 2 King Charles spaniels. … (more)"

Confirmed availability
 Christmas and New Year
11. Roger Verified Background Check

Because Pets are FAMILY TOO

Westbrook, CT, 06498

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

About: I Have taken care of pets all my life starting around age 11. I walked neighbors dogs and fed their cats when on vacation. I cared for my own cats an… (more)

12. Phurlamu Verified Background Check

I will treat your pet like my own

Cutchogue, NY, 11935

House Sitting, Dog Walking

About: I am recent college graduate at University at Buffalo. I love animals and this is a perfect way for me to balance my school work and have a job. It r… (more)

13. Andi Verified Background Check

Great hands that you can trust

Baiting Hollow, NY, 11933

House Sitting, Drop-In Visits, Dog Walking

"Andi was a great house/pet sitter. When we did the meet & greet for our trip next month, she was so kind with the dog and cat that we cancelled the other appoi… (more)"

14. Rachel Verified Background Check

animal loving college student

Old Saybrook, CT, 06475

House Sitting, Drop-In Visits, Dog Walking

About: I’ve cared for dogs my whole life personal and professionally from walks to curling up on the couch I am open to helping however I can. I can provide… (more)

15. Alexandra Verified Background Check

Lifelong animal lover and RN

East Hampton, NY, 11937

House Sitting, Drop-In Visits, Dog Walking

"I have never seen my dog fall in love with a human being faster than he did with Alex. She took care of our pup for one and a half week this June and I could n… (more)"

16. Elizabeth Verified Background Check

Dog Mom 30+ years, Give Lots of TLC

Southold, NY, 11971

House Sitting, Drop-In Visits, Dog Walking

"Elizabeth is just wonderful! Your furry friend will be walked, played with, treated to home made biscuits and most importantly loved. You will be updated wi… (more)"

17. Edwina Verified Background Check

PETS ARE LIKE CHILDREN,CHERISH THEM

Riverhead, NY, 11901

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

About: I have 35 years of experience with ALL kinds of pets. They are the innocence of life. Over the years I have had cats, dogs, an iguana, birds, hamst… (more)

Confirmed availability
 Christmas and New Year
18. Jessica Verified Enhanced Background Check

Professional & Trustworthy Pet Care

Hampton Bays, NY, 11946

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

About: I am a conscientious, non-smoking, animal loving, and trustworthy professional. From September to June, I am a Middle School Teacher. During the summ… (more)

19. Liz Verified Background Check

Caring. Reliable. Fun.

Hampton Bays, NY, 11946

House Sitting, Drop-In Visits, Dog Walking

About: I have personal history caring for midsize/large dogs, rabbits, hamsters, fish and cats. With 7 years of customer service experience with humans, my … (more)

Confirmed availability
 Christmas and New Year
20. Ella Verified Background Check

Hikes, adventures and more

Sag harbor, NY, 11963

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

"Ella and I have known each other for four years. She is responsible, reliable and smart. If she makes a commitment she will keep it. She absolutely loves dogs,… (more)"


Rover.com is the simple, savvy way to find and book Southold house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Southold on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Southold house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.