House Sitting Chester

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

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Over 14
pet parents in Chester have booked house sitting

Chester, 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.

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Sitter Profile Image: Joseph G.
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Joseph G.
from
$65
per night
5.0 out of 5 stars
• 51 reviews
17 repeat clients
2 years of experience
Chester, NY, 10918

“Joseph was spectacular while staying at our home and taking care of our dog. He was very nice and conscientious and he took great care of the house and Luna. I definitely recommend him!”

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Benny H.
Sitter Profile Image: Shannon & Justin M.
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Shannon & Justin M.
from
$75
per night
5.0 out of 5 stars
• 12 reviews
8 repeat clients
20 years of experience
Warwick, NY, 10990

“My two Jack Russell’s had a great time with Shannon while she did a 5 day house sit with them. Shannon regularly kept us up to date on their wellbeing with pictures and texts. She also was able to help us out for an extra day when our flight was delayed returning home and ensured the dogs were still taken care of while we were delayed getting home. The house looked great when we got back and we had two happy pups. Thanks again Shannon!”

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Stephanie O.
Sitter Profile Image: Chantal C.
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Chantal C.
Star Sitter
from
$80
per night
4.9 out of 5 stars
• 40 reviews
17 repeat clients
15 years of experience
Harriman, NY, 10926

“Chantal did a wonderful job watching Luna while I was away! She was very responsive, provided me plenty of updates, and left my apartment in great condition. I would definitely recommend her!!”

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Ellie H.
Sitter Profile Image: Lauren L.
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Lauren L.
from
$35
per night
10 years of experience
Chester, NY, 10918

About: Pets are family, so when I’m taking care of your child/home, I’ll keep it tidy, keep you updated, and keep in touch! I’m currently attending school full time, so I will be most available early mornings and later nights during the week. I am available all weekend Friday-Sunday. I have a big yard with a lot of land to work with. I have 2 friendly dogs of my own. I can leave a crate safely in my home as well.

Sitter Profile Image: Rachel K.
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Rachel K.
from
$50
per night
5.0 out of 5 stars
• 32 reviews
10 repeat clients
10 years of experience
New Windsor, NY, 12553

About: Hi, I’m Rachel! I’ll care for your loved one as if they were my own—whether that means long walks, playtime, or just extra cuddles. You can count on me to provide a safe, loving, and reliable environment where your dog feels like part of the family. I have a fully fenced 1-acre yard where dogs can play safely and freely, and as an athletic caretaker I’m happy to take them on long walks or runs to burn off extra energy. Whether it’s playtime in the yard or outdoor adventures, I’ll make sure your dog gets the exercise and attention they need. Please let me know of any special considerations during the visit. I will ensure and guarantee that your loved one is comfortable and has unlimited pets and snuggles while you are away.

Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$130
per night
5.0 out of 5 stars
• 55 reviews
10 repeat clients
15 years of experience
Warwick, NY, 10990

“Nicole was great with my three dogs. She is very responsive and helped when I asked her to set up a couple of things in preparation for our return as we were surprising my stepson with a few little treats!”

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Laura N.
Sitter Profile Image: Pheobe P.
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Pheobe P.
from
$55
per night
16 years of experience
Goshen, NY, 10924

About: I've grown up taking care of both cats and dogs. I love animals and look forward to helping you care your your precious pets. In the past I have worked as a pet and house sitter for a couple families. I always enjoy any time spent with animals. I have flexible schedule making me available to care for your fur babies! I live in Guerneville, but frequently go to Sebastopol throughout the week. So mainly looking to work for ones in these areas. But open to adventuring in to further surrounding areas if its a good fit for us both! Currently I am not able to board pets in my home because I am renting. But I would be happy to stop by and spend time with your pets whenever is needed!

Sitter Profile Image: Yeni A.
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Yeni A.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 32 reviews
8 repeat clients
15 years of experience
Middletown, NY, 10940

“Yeni was amazing with my dog. She was able to meet and watch him under short notice, was very professional and friendly. She followed his daily routine perfectly and sent me pics and updates during her time with him. I would totally recommend her!”

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Marie W.
Sitter Profile Image: Natalie M.
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Natalie M.
from
$95
per night
5.0 out of 5 stars
• 32 reviews
11 repeat clients
13 years of experience
Middletown, NY, 10940

About: I usually work with shy, aggressive or fearful dogs or cats. It can take weeks, months or years to befriend them but when you do it's extremely rewarding, especially when an animal someone deems "dangerous" comes out to be the biggest sweetheart. I have tons of patience and I believe every species of animal deserves love and respect. As humans, it's our duty to be the voices and guardians of the animals in our care. They look to us for comfort, guidance, love and peace. That's why I do anything in my power to donate or volunteer at animal shelters because every animal should know that there's humans out there that actually care about their well being. Working with animals is a great career for me. Update; 8/2020 I’ve been volunteering and working with pets as a professional pet care provider for five years now. Through my journey I’ve learned pet CPR and gained dog training knowledge through Poochpals llc as well as worked as a dog handler at walterspetstyles. I’m currently working on becoming a certified dog trainer and furthering my knowledge on Pet care. At Poochpals we believe in being a friend for life so I’m definitely bringing our motto into the field and looking to become a furever friend for your pets. If you’re ever in need of an actual PROFESSIONAL pet care provider, look no further! I also have basic training knowledge so don’t be surprised if your pup or cat comes back knowing a few new tricks 😂 I have open availability Monday-Sunday. I look forward to meeting you and your pups! My dog, Odin, loves to make new friends of all species. Updates:4/7/2026 Hello friends! I would not be at 29 Hanford anymore due to instability, so I’m moving my business down to NYC before heading to PA. We have multiple fences in house and around the property. Pups are also supervised 24/7 and we have a designated dog room just for them. Back porch is also secured with gates. Dogs aren’t allowed on the lawn without human supervision and a 20ft leash. Lawn is fenced. We have strict safety procedures when it comes down to pets and children.

Sitter Profile Image: Michael C.
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Michael C.
from
$30
per night
4.9 out of 5 stars
• 9 reviews
1 repeat client
10 years of experience
Florida, NY, 10921

“Michael is a wonderful dog sitter! He stayed at our home for 3 nights, and took great care of our 3 pups. We received multiple updates with photos daily. We will absolutely ask Michael to dog sit for us again.”

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Michelle S.
Sitter Profile Image: Jillian S.
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Jillian S.
from
$72
per night
5.0 out of 5 stars
• 4 reviews
16 years of experience
Greenwood Lake, NY, 10925

“Jillian was great! Very communicative and reliable. She took great care of my pup and my home. Jillian has great energy and kept my pup happy, safe and loved. I’d definitely book again!”

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Lauren P.
Sitter Profile Image: Oona S.
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Oona S.
from
$98
per night
5.0 out of 5 stars
• 8 reviews
25 years of experience
Otisville, NY, 10963

“I cannot say enough good things about Oona. She is so lovely. I came home to a very happy & healthy cat AND a clean house! She is very responsible, very engaged, very responsive and communicate - just perfect. We will be using her again and again!”

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Kristine G.
Sitter Profile Image: Madelyn M.
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Madelyn M.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 49 reviews
18 repeat clients
15 years of experience
Montague, NJ, 07827

“Madelyn took care of my 14-year old Siberian Husky, Kodiak, who has arthritis. She house-sat him while we were away on vacation for 12 days. She was wonderful with him, taking him on frequent short walks during the day. When we got home, we found a very neat house and a very happy (and tired!) dog. I would absolutely hire her again.”

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Robert Z.
Sitter Profile Image: maryanna t.
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maryanna t.
from
$35
per night
5.0 out of 5 stars
• 35 reviews
4 repeat clients
10 years of experience
New Windsor, NY, 12553

About: I’ve been working with dogs for the past ten years, up to this date. Currently work at a boarding resort, and pet sit on the side. I can confidently administer any medications, including insulin. Very skilled in dog behavior. Willing to work with skittish/fearful/“difficult” dogs. Willing to bike alongside pups who need to run if interested. I currently work for a boarding and daycare facility; our lunch breaks are usually around 12-3. Looking to help walk pups in between then and again after 6:30pm if needed. I am great at following instructions, and safety is my biggest priority. I take my time gaining a dogs trust, and strive for maximum comfort in an already stressful situation.

Sitter Profile Image: Miranda C.
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Miranda C.
from
$35
per night
4 years of experience
Monroe, NY, 10950

About: I’ve taken care of my family’s animals and neighborhood pets for neighbors for a few years now. I love taking your furry friends on walks or hikes to get all their energy out! Ive cat sit as well for people. And have experience working with puppies and taking care of senior animals I work a part time schedual that changes and has flexibility! Message me and we can talk times and details! I am almost always available for walks/drop ins in the morning before work and after I have 2 friendly dogs, and 2 quiet cats. I have a little less than an acre for them to run around, be advised no fence.

Sitter Profile Image: Thu T.
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Thu T.
from
$75
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Newburgh, NY, 12550

“Thu was amazing. I had another sitter booked who canceled on me on Thanksgiving morning! Thu saved the day! She spent lots of time loving my babies and sent me pictures. I would highly recommend her.”

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Michelle M.
Sitter Profile Image: Erica G.
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Erica G.
from
$45
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
16 years of experience
Walden, NY, 12586

“Erica came through in a pinch and provided outstanding service for our pets when we were in need. She is very friendly, understanding and flexible with her schedule and both of our pets felt at ease with her. During her stay she was excellent with communication and provided photos and texts that assured us that everything was going great!”

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Pam V.
Sitter Profile Image: Katarzyna R.
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Katarzyna R.
from
$55
per night
4.9 out of 5 stars
• 71 reviews
15 repeat clients
24 years of experience
Bloomingburg, NY, 12721

“My family and I had to be away from home over night so we decided to look on Rover to find the perfect person who would accommodate us last minute.. and after reading only three reviews we found Katarzyna and we Brought our 2 yrs pit mix Kash to her.. we were nervous because Kash exposure to other were at the dog park.. he immediately take to Katarzyna.. see send me pictures of Kash and we were comfortable knowing he will be cared for.. will definitely ask Katarzyna to watch him again.,Thank you so much.”

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Opal W.
Sitter Profile Image: Nicole T.
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Nicole T.
from
$60
per night
4.3 out of 5 stars
• 6 reviews
1 repeat client
3 years of experience
Buchanan, NY, 10511

“Nicole provided exceptional care for our dog during our week out of town. She was our first Rover hire, and we have no complaints, just appreciation! Our dog Lucy has a lot of anxiety about new experiences and people, but she loved Nicole! We definitely will book Nicole again in the future.”

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Julia H.
Sitter Profile Image: Vincenzo C.
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Vincenzo C.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
7 years of experience
Garrison, NY, 10524

“Vinny did an excellent job taking care of our pets and house while we were away on an international trip! He left the house better than he found it - I was very impressed by his thorough cleaning and obvious caretaking of our pets. I don’t think our fur babies even realized we were gone! I would absolutely recommend Vinny for anyone interested in house+petsitting.”

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Ally F.
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The median cost per night for house sitting in Chester is $65

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 - Chester

Select a filter and find qualifying sitters offering house sitting.

Sitters in Chester average 3
repeat house sitting clients

FAQs for House Sitting - Chester

Frequently asked questions about Rover

The average cost of House Sitting in Chester is $87 per night as of November 2026. Most bookings cost between $58 and $107 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 1,470 sitters on Rover offering House Sitting across Chester. 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 Chester 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 Chester 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 Chester 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 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 Meet & Greet.

sitters on Rover set their own cancellation policy, 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 Chester. On Rover:

  • 88% of sitters can help with special care needs
  • 93% 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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