House Sitting in Chester

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Top rated Chester house sitters

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: Eryn K.
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Eryn K.
Star Sitter
from
$85
per night
5.0 out of 5 stars
185 reviews
56 repeat clients
5 years of experience
Florida, NY, 10921

Eryn was absolutely amazing with the animals! She sent me pictures throughout the stay and sent me updates to ensure everything went smoothly :)

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Jacquelyn E.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$60
per night
5.0 out of 5 stars
14 reviews
6 repeat clients
15 years of experience
Middletown, NY, 10940

Vicky watch my dog Prince for a week while I was away in that time Print became sick with a cough. Vicky kindly stayed in communication with me as I scheduled a vet visit. Photos were sent daily and Prince had a good time. Her price was slightly lower than other Rover’s which I liked! She did a great job and I would choose her again in the future

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Alexis C.
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$130
per night
5.0 out of 5 stars
47 reviews
5 repeat clients
15 years of experience
Chester, NY, 10918

Nicole was excellent from start to finish. She was prompt, communicative, and caring for our pets and home. She sent us a ton of photos and left the house in a pristine condition. I would absolutely recommend her for all of your pet and house sitting needs.

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Alex E.
Sitter Profile Image: Kristina G.
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Kristina G.
from
$50
per night
4.9 out of 5 stars
12 reviews
4 repeat clients
24 years of experience
Mechanicstown, NY, 10940

Kristina is absolutely wonderful. We booked her kind of last minute as our previous sitter fell through. She was accommodating and made our anxious dog comfortable while she stayed in our home with him. I highly recommend Kristina & will absolutely book her again in the future if she is available.

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Taylor B.
Sitter Profile Image: Jill S.
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Jill S.
from
$75
per night
5.0 out of 5 stars
175 reviews
46 repeat clients
57 years of experience
Washingtonville, NY, 10992

Jill took great care of our doggos! We are very happy we found her and have already booked for a repeat stay later this summer. We booked way in advance and she was great about coming to meet the dogs, not once (early), but twice (the week of our trip). You can tell she loves dogs and was so patient with our shy one. She was very responsive and sent lots of pictures!

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Mollie S.
Sitter Profile Image: Robbie O.
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Robbie O.
from
$70
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
30 years of experience
Campbell Hall, NY, 10916

Robbie was nothing short of heaven sent! When we had to make last minute changes for our dogs’s care Robbie took the time to come over, get acclimated with our two large dogs and learn their routine to keep them comfortable as it was their first time with care from a sitter. When our flight was canceled due to a snow storm, she continued to show up for them and even took them out to play in the snow and sent us pics to keep our minds at ease. She was caring, respectful to our home and really went above and beyond in so many ways. You can tell she’s a real animal lover and we are so grateful she cared for our pups!

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Manny A.
Sitter Profile Image: Linda B.
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Linda B.
Star Sitter
from
$100
per night
5.0 out of 5 stars
29 reviews
14 repeat clients
25 years of experience
Goshen, NY, 10924

About: I am in the Middletown- goshen area of Orange County and can’t board any animals at our new home. I prefer a meet and greet before booking and have excellent references. I can walk, spend time with , and play with your dogs and/or cats. I’m experienced with administering medications to both. I have references from my customers in Sullivan county where I used to live if needed . Recently retired I now have a very open schedule for your vacations or weekend needs. I have been an Eagle nest monitor for the NYDEC from 2011 - 2019 on the Delaware River and on Yankee Lake NY 2013- 2022 and have been involved in animal rescue . *That means I have both domestic animal and wildlife experience. I have been a local volunteer and continue to involved in my community. I am newly retired and can come anytime that fits into your schedule . Hopefully I can be the person you call for your vacation or special occasions. Sadly, I no longer have a place to board any animals. But I do have some great references and would provide them upon request. I do have a medium size pup of my own I can bring if you have a friendly dog.

Sitter Profile Image: Leangie M.
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Leangie M.
from
$35
per night
4 years of experience
Goshen, NY, 10924

About: Our pets are more than just companions. They are family, this makes them so much more precious. Which is why with me I can guarantee that I will do my best to provide the love and care your pet deserves. I have cared for dogs young and old, big and small, calm and energetic, you name it. I have experience feeding, cleaning after them as well as themselves, and giving medications with specific instruction. I am available all night on Monday into the evening on Tuesdays. As well as in the evening on Fridays up until the evening on Sunday. Other days of the week are very negotiable to what you may need! I personally love to encourage as much activity as possible with my dogs to ensure they get healthy amounts of play time. This in turn allows them to get ample rest when they are tired from activity further encouraging a healthy lifestyle for my furry kiddos.

Sitter Profile Image: Tessa D.
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Tessa D.
from
$75
per night
5.0 out of 5 stars
4 reviews
1 repeat client
14 years of experience
Warwick, NY, 10990

About: I’ve been taking care of pets my entire life, and my family and friends look to me if they need me to dog sit (or pet sit) when they’re away or unavailable. I love animals, and so getting to take care of furry friends is an absolute treat!! I’m currently attending college, so monday and wednesday mornings im out of the house from 8-12. any other time, if given enough notice, i can be available for you and your pets! I live in a family home with my dog daisy, who is very friendly and about 14 years old now. She never fails to be entertained, and I love her with all my heart. I will do the same for your pets :)

Sitter Profile Image: Teadie Marie F.
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Teadie Marie F.
from
$95
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
15 years of experience
Harriman, NY, 10926

Thank you, Teadie, for taking such good care of our Imo. Your photos and frequent updates enabled us to really enjoy our vacation. Imo was very content upon our return and, we’re sure, would enjoy your sitting for him again!!! And thank you for taking care of the linen and towels…you didn’t need to do that, but it was very much appreciated!

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Lee K.
Sitter Profile Image: Madison F.
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Madison F.
Star Sitter
from
$35
per night
5.0 out of 5 stars
6 reviews
4 repeat clients
3 years of experience
University, Newburgh, NY, 12550

She was punctual and had great communication. We received nice updates as well as photos throughout the visit. We have already rebooked!

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Erin A.
Sitter Profile Image: Amber C.
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Amber C.
from
$78
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
25 years of experience
Chester, NY, 10918

Amber did a great job petsitting for our 2 dogs and 2 cats! She took care of all their needs and they were so happy to spend time with her.

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Corinne Z.
Sitter Profile Image: Michael C.
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Michael C.
from
$30
per night
4.9 out of 5 stars
8 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: Sophie G.
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Sophie G.
from
$50
per night
5.0 out of 5 stars
8 reviews
1 repeat client
13 years of experience
Middletown, NY, 10940

Sophie did a great job with my Golden Retriever, Miller. She gave him a lot of exercise, kept him engaged, and followed all of my requests. I will definitely be requesting Sophie again for future house sitting needs!

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Kallie T.
Sitter Profile Image: Colleen R.
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Colleen R.
from
$45
per night
5.0 out of 5 stars
7 reviews
1 repeat client
7 years of experience
New Windsor, NY, 12553

She was fantastic! We have 2 cats and 2 dogs. She pet sat at our house when I needed to fly to Florida last minute for a family emergency. Colleen, sent us updates with pictures. Gave me such a peace of mind while gone to know my fur babies were in good hands!

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Stephanie F.
Sitter Profile Image: Maytte B.
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Maytte B.
from
$55
per night
5.0 out of 5 stars
4 reviews
14 years of experience
West Milford, NJ, 07421

May was great! She is very responsible. She sent updates during her dogsitting and did a good job handling my very energetic Belgian Malinois. I will definitly use her again!

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Nick D.
Sitter Profile Image: Shannon & Justin M.
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Shannon & Justin M.
from
$75
per night
5.0 out of 5 stars
8 reviews
7 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: Emma W.
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Emma W.
from
$45
per night
4.8 out of 5 stars
6 reviews
1 repeat client
22 years of experience
New Hampton, NY, 10958

Emma has been great with Augie. We’ve had her for walks and housesitting. She keeps him very entertained and very happy and we get lots of fun pictures! She treats him like he’s her own 😊

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Kimberly B.
Sitter Profile Image: Natalie H.
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Natalie H.
from
$90
per night
6 years of experience
Monroe, NY, 10950

About: From the age of 4 i’ve had two cats. Now I have two dogs as well. Both rescues one a mutt, and another a pit mix. Outside of my own pets I have taken care of friends, family, and neighbors pets. Whether it be walking, drop-in visits or staying overnight I love taking care of all animals. If needed, I can help medicate too. I have a flexible schedule and my own car. I’m here to be a last minute carer, or a reliable and stable carer for your pets. I am available for walking, drop-in visits, and overnight stays. With my own car I am willing and able to drive far distances. I will care for your pets by communicating clearly with you on any and all their needs. I will treat your home and your animals with care. I will love your pets like my own!

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Over 25
pet parents in Chester have booked house sitting

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 house 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.

Sitters in Chester average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chester on Rover as of Jun 2026 was about $65 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Chester house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 683 house sitters in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 85% of Chester house sitters respond in under an hour.

House sitters in Chester have an average of 17 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chester.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chester house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.