House Sitting Head of the Harbor

Find a loving house sitter to watch over your pets and your home.

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Over 26
pet parents in Head of the Harbor have booked house sitting

Head of the Harbor, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Amanda M.
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Amanda M.
Star Sitter
from
$80
per night
5.0 out of 5 stars
22 reviews
8 repeat clients
15 years of experience
Farmingville, NY, 11738

Another wonderful job by Amanda! Our elder dog Chelsea was getting over not feeling well and Amanda cared for her like she was her own. She gave lots of feedback and pics. Showered our Chelsea Girl with attention. Will book again!

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Dawn G.
Sitter Profile Image: Walter B.
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Walter B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
15 reviews
8 repeat clients
7 years of experience
Stony Brook, NY, 01810

About: I’ve grown up taking care of animals with my own pets. Have experience dog sitting and walking with puppy’s through elderly dogs. Always have been passionate about being dogs best friend. I am currently a student at Stony Brook taking 14 credits during the day. Message me for drop in visits or walking to find a time that works for the both of us. My home has a natural fence of a swamp. I take my elderly dog (Esther) out on walks every other day (ussally the beach) and on the off days we stay out in the back yard playing fetch. This seems to be the best schedule for an elderly dog full of life but with fading joints.

Sitter Profile Image: Asher W.
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Asher W.
from
$60
per night
5.0 out of 5 stars
5 reviews
2 years of experience
Stony Brook, NY, 11790

Asher did a great job taking care of our 5 year old lab while we were away for the weekend. We returned to a happy dog and a well cared for house. I highly recommend him and plan on using him again.

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Madeline T.
Sitter Profile Image: Magdalena M.
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Magdalena M.
from
$60
per night
1 repeat client
20 years of experience
Stony Brook, NY, 11790

About: I was raised with dogs from the time I was born, and our home was always full of animals — be it bunnies, turtles, hamsters or parrots! I’m now a proud pet mom to two cats, Tortellini and Simone, and one pup, Frankie. I understand how important it is to find someone trustworthy, patient, and attentive to care for your pets while you’re away. My pup, Frankie, is always happy to make new furry friends, and I love making sure every pet feels safe, comfortable, and loved. Whether your pet needs feeding, walks, playtime, litter box care, medication reminders, or just extra love and companionship, I’ll treat them like part of my own family. Pet care fits very naturally into my routine because I’m a researcher who works from home, so my schedule is flexible throughout the week. I’m available for weekday care, weekends, drop-ins, walks, and overnight stays. Since I spend a lot of time at home, I’m able to give pets plenty of attention, companionship, and consistency. I’m happy to work around your pet’s usual routine so they feel safe, comfortable, and cared for while you’re away. I currently offer care in my client’s home, where pets can stay comfortable in their own familiar environment. I’m very respectful of each home and each pet’s routine, and I’m happy to follow detailed instructions for feeding, walks, litter box care, playtime, medications, and any special needs. I’m also comfortable managing different household setups, including keeping pets separated when needed, handling multi-pet homes, monitoring doors/gates carefully, and making sure each pet feels safe, calm, and cared for.

Sitter Profile Image: Sharon P.
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Sharon P.
from
$100
per night
5.0 out of 5 stars
134 reviews
42 repeat clients
30 years of experience
Stony brook, NY, 11790

Sharon was great and very professional. She followed all instructions to the letter and went above and beyond to leave my home clean and orderly. Mandy and Max love her!

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Diane F.
Sitter Profile Image: Melissa S.
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Melissa S.
from
$50
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
5 years of experience
Port Jefferson Station, NY, 11776

Melissa is simply amazing. We have re-booked her over 10 times for home visits and home sitting our pet, Scott. We all were going on an international trip of ~10 days and we were worried since this was the first time we using someone’s services to stay at home and take care of Scott. Punctuality is Melissa’s virtue and Scott was absolutely comfortable with her. All those 10 days, we were very peaceful and Melissa ensured, with pictures and videos of Scott, that we were always in touch! A very big shout out to Melissa for a fantastic service!

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Prabhu M.
Sitter Profile Image: Jess P.
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Jess P.
from
$100
per night
5.0 out of 5 stars
47 reviews
16 repeat clients
10 years of experience
Smithtown, NY, 11787

Jess was wonderful with our golden retriever! She was prompt, efficient and communicative which eased any worry we had. I would definitely recommend Jess for any dog service you need!

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Melissa L.
Sitter Profile Image: Kimberly B.
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Kimberly B.
Star Sitter
from
$125
per night
5.0 out of 5 stars
151 reviews
26 repeat clients
16 years of experience
Lake Grove, NY, 11755

Kim is awesome! I felt 100% comfortable leaving my pup knowing he was with her. She clearly both loves and understands dogs and is reliable, a good communicator, and lovely to deal with. I came home to a happy and well cared for dog. Thank you!

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Kimberly C.
Sitter Profile Image: Kelly C.
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Kelly C.
Star Sitter
from
$88
per night
5.0 out of 5 stars
23 reviews
13 repeat clients
16 years of experience
Ronkonkoma, NY, 11779

Kelly was such a great caretaker for our babies and our house! She is so patient and loving; she took excellent care of everyone; and she gave us frequent photos and updates while staying at our house. We will absolutely ask her to care for our pets again!

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Jennifer B.
Sitter Profile Image: Ava W.
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Ava W.
Star Sitter
from
$46
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
6 years of experience
kings park, NY, 11754

Ava is very responsible and conscientious. She sent lots of photos and checked in when she had questions, as well as responded to my questions. Max was well taken care of while we were away!

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Star V.
Sitter Profile Image: Staci G.
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Staci G.
Star Sitter
from
$85
per night
5.0 out of 5 stars
46 reviews
10 repeat clients
30 years of experience
Ronkonkoma, NY, 11779

Staci was so great, her communication was prompt and she kept me updated throughout her visit with photos. She was able to help me out in a pinch and my baby was well taken care of. I’m so appreciative of that. I will definitely be working with her again!

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Kendall W.
Sitter Profile Image: Shannon W.
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Shannon W.
from
$65
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Port Jefferson, NY, 11777

Shannon was such a great sitter. The pups took an instant liking to her. She was excellent at communicating and keeping me updated. I certainly will book her again should the opportunity arise. Highly recommend! Thanks Shannon.

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Artie G.
Sitter Profile Image: Tatiana F.
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Tatiana F.
from
$55
per night
5.0 out of 5 stars
11 reviews
1 repeat client
15 years of experience
Smithtown, NY, 11787

Tatiana did a fantastic job watching my puppy Wesley today. She played outside with him and sent me texts and pictures throughout the day. I would highly recommend her and can’t wait to book future events. I felt completely confident leaving my fur baby with her.

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Andria F.
Sitter Profile Image: Nicole F.
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Nicole F.
from
$95
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
10 years of experience
Stony Brook, NY, 11790

We are so happy we met Nicole to watch our 2 pups and cat while we were away. She handled our 2 big pups like a pro - they are not the easiest and are a bit on guard when meeting new people but she quickly put them at ease. She sent daily updates and followed our instructions perfectly. I am very happy that we have Nicole to trust with our animals!

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Sharon K.
Sitter Profile Image: Cynthia A.
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Cynthia A.
from
$70
per night
5.0 out of 5 stars
38 reviews
19 repeat clients
59 years of experience
Farmingville, NY, 11738

Hands down best dog sitter I’ve ever had. I’ve never felt more comfortable leaving my baby with anyone else. I received photos and updates throughout the day and the experience with dogs was unmatched. Thank you! Will definitely use again!!!

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Theryn G.
Sitter Profile Image: Riley F.
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Riley F.
from
$65
per night
1 repeat client
3 years of experience
Stony Brook, NY, 11790

About: I’ve always possessed a deep love for animals and have grown up around pets my entire life. I have several years of hands-on experience working at a grooming salon, where I assisted with bathing, feeding, and caring for dogs of all breeds and temperaments. I’ve also volunteered at local animal shelters, which helped me better understand dog behavior, body language, and each pet’s unique emotional needs. I’m patient, dependable, and committed to making every pet feel safe, comfortable, and loved while you’re away. I would be honored to care for your furry family member like they’re my own! 🐾 I recently graduated and am taking a gap year, pursuing additional courses as an aspiring physician assistant and working part-time in healthcare. My schedule is very flexible throughout the week, which allows me to dedicate plenty of time, attention, and care to your pets. I’m generally available most weekdays and weekends, except Thursdays. Your pet’s safety and comfort are my top priorities. I always take the time to understand each dog’s routine, personality, and needs to help them feel comfortable and cared for while you’re away. I’m attentive to body language, feeding schedules, medications if needed, and making sure pets feel safe, loved, and stress-free in their own environment. I’m also happy to provide regular updates and photos for peace of mind.

Sitter Profile Image: Zachary R.
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Zachary R.
from
$35
per night
20 years of experience
St James, NY, 11780

About: I’ve always had animals in my life and taken care of dogs and cats since I was little. There is nothing quite like having a pet; nurturing it yourself, forming that special bond and learning all those quirks that make each animal special. My own dog Maxie is very social and even at 10 years old is super playful. I wanted to be a pet sitter because I enjoy being around animals and taking care of them. It always makes my day meeting a new dog. I am comfortable with any kind of breed and any age. My hours are flexible and I have over 20 years experience. I am a teacher, I generally work from 7-2 but I available before 7 to make sure they are well fed. I can also come back on my lunch breaks to make sure they get some play time and need to go for walks as well as anytime after 2:30. I am also available on Saturdays and most Sundays. I would bring toys and treats for your fur baby so that they feel comfortable with me. I would ask their owners what their routine is and if they have any medical concerns I should be aware of. I would send them pictures of their pets throughout the day and keep their owners regularly updated on how they are doing. I normally walk my dog 3 times a day and feed him twice a day ( morning and night ) with snacks in the middle of the day with plenty of water and potty breaks. I would be doing the same things too. I usually play with my dog first thing when I get home and before we go to bed. I would do the same things too when I pet sit.

Sitter Profile Image: Nicolas L.
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Nicolas L.
from
$65
per night
6 years of experience
Near East, Port Jefferson, NY, 11777

About: I absolutely love animals!! I had a Schnauzer named Loki years ago. I decided I wouldn’t have another puppy, but I’ve been having a blast watching other people’s dogs. It’s kind of like a fun uncle type of situation I’ve been thriving on lately. I have tons of experience watching and handling animals. Since my youth, I’ve been in love with nature. I even became an Eagle Scout! I’m passionate about animals and all life in general. I even thought about becoming a vegan, but that’s another topic of discussion… I’m a yoga instructor, so my schedule is very flexible. My free time is spent running, exercising, and studying. You can find me either outdoors or at a coffee shop! I am very communicative and attentive, so you can expect multiple text messages with updates on how your puppy is doing. Expect mini photo shoots!

Sitter Profile Image: Tricia P.
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Tricia P.
Star Sitter
from
$63
per night
5.0 out of 5 stars
56 reviews
12 repeat clients
13 years of experience
Patchogue, NY, 11772

Trisha graciously watched my 2 older dogs at the last minute in my home. She was an amazing houseguest, and was incredible with my visually impaired dog who requires various daily medications. My other grumpy dog took to Trisha immediately, which is remarkable as he can be stingy with his affection. Thank you Trisha and we all look forward to seeing you again soon.❤️

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Joanna S.
Sitter Profile Image: Cara B.
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Cara B.
from
$68
per night
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Port Jefferson, NY, 11777

Cara takes great care of my dog, and always makes sure to provide prompt updates and photos. She’s a pro!

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Margaret S.
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The median cost per night for house sitting in Head of the Harbor is $65

Pet parents share their Rover experiences - Head of the Harbor

1 / 1
5.0 out of 5 stars

Tatiana was an amazing dog sitter for our dog, Steely! She kept us updated the entire weekend with messages and photos, which gave us so much peace of mind while we were away. It was very clear that Steely was well cared for, loved, and comfortable the whole time. We truly appreciated her communication, reliability, and kindness. We would absolutely recommend Tatiana to anyone looking for a trustworthy and caring pet sitter!

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Christine H.
House Sitting
5.0 out of 5 stars

Kimberly was so amazing while she watched my dog Rocky. She saw signs of anxiety, but went at his own pace and she’s really experienced. I felt really relieved, knowing that my dog was in good hands. Highly recommend.

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Christine V.
House Sitting
5.0 out of 5 stars

Elisa was amazing! She took great care of our dogs and our home. She sent lots of pictures and gave plenty of updates. It was so nice being able to travel with the peace of mind that everything back at home was in good hands.

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Bob S.
House Sitting
5.0 out of 5 stars

Sharon was wonderful with our Eloise! She sent pictures and kept in constant contact with us. We had peace of mind and were able to enjoy our getaway. Will definitely use her again!

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Carol G.
House Sitting
5.0 out of 5 stars

Asher did a great job taking care of our 5 year old lab while we were away for the weekend. We returned to a happy dog and a well cared for house. I highly recommend him and plan on using him again.

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Madeline T.
House Sitting
5.0 out of 5 stars

Bridget was amazing with our dog Beau and our house. Beau was well taken care of while we were gone and Bridget was so responsive with messages. Our house was spotless when we got back and I would 1000% have Bridget take care of Beau for our next trip!

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Carolyn S.
House Sitting
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

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Select a filter and find qualifying Head of the Harbor sitters!

Sitters in Head of the Harbor average 3
repeat house sitting clients

FAQs for House Sitting - Head of the Harbor

Frequently asked questions about Rover

The average cost for House Sitting in Head of the Harbor on Rover is $86.03 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 3,071 sitters on Rover offering House Sitting across Head of the Harbor. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Head of the Harbor walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Head of the Harbor maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Head of the Harbor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Head of the Harbor. On Rover:

  • 90% of sitters can help with special care needs
  • 91% can help with giving oral medications or injections
  • 97% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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