House Sitting Wainscott

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

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Sitter Profile Image: Brian V.
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Brian V.
from
$125
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
5 years of experience
East Hampton, NY, 11937

“Brian was great with our two pups. One of them is extremely shy, and he was able to make him feel comfortable right away. We trusted that they were being well taken care of while we were gone, so we could enjoy our time away.”

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Lorinda B.
Sitter Profile Image: Lindsey F.
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Lindsey F.
from
$100
per night
18 years of experience
Bridgehampton, NY, 11932

About: I am a loving, responsible, reliable, friendly 38 year old who loves animals, especially dogs! I was born and raised in Southampton, NY. I work full time as a Human Resources manager for a company in NYC (I go into the city 2-3 days a week). I am looking to make some extra money and keep busy on my off days and remote work days, and why not do that by doing something I love! I can do dog walking/visits/feedings before, and I can do overnights (at your home or mine) as long as I am not out of town. I have many years of dog sitting (some cat) experience with dogs of all sizes and breeds. My entire life I have had at least one dog in my family home, I promise your dog will be in safe and loving hands!!! I am genially available as long as I’m not in the city for work. I go into the city 2-3 days per week but otherwise I’m very flexible! My home is safe and pet friendly. I can fit a crate if needed. I have yard space to walk dogs and live in a walkable neighborhood to take longer walks as well.

Sitter Profile Image: Mary M.
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Mary M.
from
$150
per night
1 year of experience
Sag Harbor, NY, 11963

About: Available for boarding or sitting dogs. ♥️ Love dogs and have experience. Must be fully vaccinated please. Here is my dog, Harry! Look forward to helping! Thank you Hello! There is lots of availability. Please let me know your preferred dates and daily schedule for your dog! Thank you and looking forward to comforting your dog! I love dogs and would love to help with boarding or sitting! All dogs must be vaccinated please. Look forward to comforting your dog! Thank you

Sitter Profile Image: Maria E.
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Maria E.
from
$160
per night
4.9 out of 5 stars
• 64 reviews
23 repeat clients
25 years of experience
Sag Harbor, NY, 11963

“maria was great. professional, personable and took great care of our pup. i’d definitely hire her again.”

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Steven H.
Sitter Profile Image: Blythe P.
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Blythe P.
from
$100
per night
40 years of experience
Hampton Bays, NY, 11946

About: I have cared for my own animals for 20+ years and the older I get the more I love my dog. I currently have a dog named Sage she is a mutt and she is the biggest sweety. She also enjoys other dogs and is the best sister to her 3 cat brothers and sister and Bunny She also is very gentle with our 7 chickens that we let free range. We can keep them in their run if your dog isn’t as comfortable with the birds 😹 I love to take my dog to the beach and get our beach walks in and also chilling in the fenced in backyard. If you would rather your furry to stay home I am also very comfortable house staying. I have been a massage therapist for 25 years and feel very comfortable being in others spaces. Whatever the setting know your pup is safe and cared for like my own. I am currently freelance in my massage business so I have plenty of time and flexibility to spend time and walk your pup. And having a spacious backyard allows for play time too. I have a fenced in yard and also live on a very quiet dead end street in a quiet neighborhood where I enjoy walking the dogs. Where ever I am I always am sure to keep the dogs leashed.

Sitter Profile Image: Alexandra R.
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Alexandra R.
from
$35
per night
8 years of experience
East Quogue, NY, 11942

About: I’ve had dogs my whole life, from the day I was born to now! I volunteered at an animal shelter for a year too! I love animals and I love working with them, and hopefully that will become my future career♥️ I take care of my dogs daily and I walk them everyday. I am currently a full time student at a college, so for the summer I will be available every day. But starting late August, I will be starting my 3rd semester so I will be only available on the weekend’s! I wash my dogs, I take them on long walks, I feed them, and they love to cuddle. They are now senior dogs, so they sleep more often, but they are given the love and care that they need!😊

Sitter Profile Image: Lindsay r.
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Lindsay r.
from
$70
per night
4.8 out of 5 stars
• 6 reviews
3 repeat clients
10 years of experience
Westhampton, NY, 11977

About: I have grown up with dogs and various other animals my whole life!! I’m a huge animal lover and will treat your dog like my own :) I currently am a part time student so I have plenty of time to give to your dogs the full attention they need and deserve! I have a very large, isolated, fenced in yard that my old dog loved to play in!! I can crate your dog easily if needed!

Sitter Profile Image: Thomas H.
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Thomas H.
from
$80
per night
35 years of experience
Farmingville, NY, 11738

About: I have over 35 years of experience caring for dogs, having grown up with them and always been around them. I specialize in taking dogs on long walks and engaging them in play, making sure they get the exercise they need. I've cared for dogs belonging to neighbors, friends, family members, and other clients, which has broadened my experience with different breeds and personalities. I work part-time and care for my elderly father, which gives me a flexible schedule for dog walking and weekend pet sitting. I lead an active lifestyle and love taking dogs on long walks and playing with them to keep them happy and healthy. I provide a safe and comfortable environment for pets at their home. I follow their routines and ensure they feel secure and cared for. Keeping pets safe is my top priority, whether I’m walking them or watching them at home.

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The median cost per night for house sitting in Wainscott is $75

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for house sitting - Wainscott

Select a filter and find qualifying sitters offering house sitting.

Sitters in Wainscott average 3
repeat house sitting clients

FAQs for House Sitting - Wainscott

Frequently asked questions about Rover

As of October 2026, there are 317 sitters on Rover offering House Sitting across Wainscott. 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 Wainscott 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 Wainscott 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 Wainscott 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 , 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 .

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

Yes, you can find sitters who have experience with handling special pet needs in Wainscott. On Rover:

  • 91% of sitters can help with special care needs
  • 93% can help with giving oral medications or injections
  • 98% 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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