House Sitting in Chester

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

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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: Wendy B.
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Wendy B.
from
$63
per night
5.0 out of 5.0 stars
30 reviews
7 repeat clients
54 years of experience
Queenstown, MD, 21658

She was excellent! She took great care of our cat as well as our house. I would highly recommend Wendy and plan on using her again for a 3 week trip I plan in July.

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Doris G.
Sitter Profile Image: Cristina M.
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Cristina M.
from
$75
per night
5.0 out of 5.0 stars
7 reviews
25 years of experience
Stevensville, MD, 21666

I highly recommend Cristina. Our timid Italian Greyhound warmed up to her quickly and even our cat came out for a cameo visit. She communicated well and sent pictures of the kids. I will be using her again! Thank you Cristina J

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James M.
Sitter Profile Image: Taylor M.
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Taylor M.
Star Sitter
from
$55
per night
5.0 out of 5.0 stars
13 reviews
7 repeat clients
12 years of experience
Stevensville, MD, 21666

Taylor is fantastic - patient with my grouchy old pup and kept up with my hyper young Aussie. An overnight trip was a stress-free experience for me and the dogs thanks to Taylor!

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Cait B.
Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$75
per night
5.0 out of 5.0 stars
17 reviews
4 repeat clients
20 years of experience
Stevensville, MD, 21666

Lena was fantastic. She communicated often so we knew how our dog was doing. She took great care of our dog gave her lots of love and plenty of exercise. We would highly recommend !!!

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Su B.
Sitter Profile Image: Payton W.
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Payton W.
from
$50
per night
4.5 out of 5.0 stars
3 reviews
1 repeat client
6 years of experience
Stevensville, MD, 21666

About: I have experience taking care of cats and dogs going back to my early teens. I’m just as much a cat lover as I am a dog lover and would love to take care of your fur babies. Whether you have a sweet big dog or a little shy cat, I love them all the same. Most of my family has at-least 2 or more cats or dogs and they often rely on me to take care of them when they go on vacation, have a long work week, or just need a helping hand. I currently work full time, 9-5 Monday through Friday. Most of my availability is on the weekends or late afternoons. But depending on the request I may be able to make an exception. I have experience caring for small dogs, big dogs, shy cats, energetic cats, senior dogs and cats. I’ve cared for almost every type of pet there is. I’ve even cared for reptiles and guinea pigs. Whether your pet would like space and quiet or someone to help them get their energy out I can provide that. I can meet the needs of your pet. Every dog/cat is different and I’m here for it all 😊

Sitter Profile Image: Julie K.
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Julie K.
from
$50
per night
5.0 out of 5.0 stars
4 reviews
1 repeat client
5 years of experience
Chester, MD, 21619

Julie was fantastic! Communicate her arrival, departure, updates on the pups, pictures. Tesla and Eevie were content and happy. Glad I found her; recommended and I will have her watch the pups anytime!

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Josefina P.
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
from
$30
per night
5.0 out of 5.0 stars
73 reviews
27 repeat clients
22 years of experience
Stevensville, MD, 21666

Bo is so great! Rowdy and a new bff, for sure. She is extremely communicative, caring, and respectful. Our dog was walked to his heart’s content, loved on and well cared for while we were away. She even changed the sheets so a following house sitter wouldn’t need to do it when he arrived. We will book Bo again for sure, and Rowdy is thrilled.

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Julia C.
Sitter Profile Image: Savannah T.
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Savannah T.
from
$25
per night
5.0 out of 5.0 stars
2 reviews
1 repeat client
1 year of experience
Stevensville, MD, 21666

Savannah was awesome. We left our two goldens with her for weekend in our home. When we returned everyone was happy! We will definitely use her again

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Ron S.
Sitter Profile Image: Karen R.
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Karen R.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
6 reviews
3 repeat clients
15 years of experience
Annapolis, MD, 21401

Karen was great with our four animals (dogs and cats)! Karen was communicative, provided great updates, and let us know when one of our cats was having a minor potential health issue. Would recommend and I know our pets are already looking towards when Karen will be back to see them again!

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Marie C.
Sitter Profile Image: Lindsay G.
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Lindsay G.
from
$50
per night
5.0 out of 5.0 stars
2 reviews
3 years of experience
Stevensville, MD, 21666

About: I have been a pet care attendant at a dog kennel for two years now. My responsibilities include feeding, walking, playing, bathing/grooming, and administering medications for animals. I have training in dog behavior as well as any medical needs of animals. I also come from a veterinary medical background and have watched and walked dogs for members of my community for many years. I have experience dealing with aggressive, dog reactive, leash reactive, cage brave, and resource guarding animals as well as any other needs that your pet may have. I am currently enrolled at the University of Maryland but can make time to walk and care for pets around my school schedule. I am at my apartment all other times of the day and will be easily available to care for pets. I live in an apartment currently but can easily crate your animals when leaving for class. I live in a pet friendly community with no others pets living in my apartment and can easily walk your pet around my community or take them to the courtyard in my apartment for a quick potty break. There is also an animal bathing room in my apartment complex so I am able to bathe your animals if needed.

Sitter Profile Image: Jason & Tracy Y.
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Jason & Tracy Y.
from
$28
per night
4.9 out of 5.0 stars
77 reviews
30 repeat clients
10 years of experience
Stevensville, MD, 21666

Jason & Tracy are awesome!!! I just came back from an Alaskan cruise and I never had to worry about Little Buddy, my cat! They took such loving care of him as if he were their own! Every time I came into port and got wifi signal, there was a new picture of Little Buddy looking very content! You couldn't ask for better TLC for your cat or dog!! :-)

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Paula C.
Sitter Profile Image: Sean K.
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Sean K.
from
$35
per night
5.0 out of 5.0 stars
1 review
1 repeat client
10 years of experience
Stevensville, MD, 21666

About: I've always been great with animals, able to read them and good at figuring out what they need. I volunteered at Animal Welfare League of Queen Anne's County for several years starting in High School. I've worked closely with large animals with behavioral problems, so I'm down the handle whatever quirks your pet has. I am currently getting my master's degree in Annapolis. I have classes and work twice a week but can still provide services with enough prior notice. I'm very adept at reading animals behavior and figuring out when they need attention, when they need space, and good at gaining an animals' trust.

Sitter Profile Image: Camilla G.
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Camilla G.
Star Sitter
from
$70
per night
5.0 out of 5.0 stars
11 reviews
3 repeat clients
5 years of experience
Annapolis, MD, 21403

Camilla was terrific. She took amazing care of my 3 dogs -2 who are not easy. She sent updates and pics. House was very clean when we got back. Would definitely recommend!!

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Nicole D.
Sitter Profile Image: Alexia M.
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Alexia M.
from
$30
per night
5.0 out of 5.0 stars
10 reviews
4 repeat clients
5 years of experience
Annapolis, MD, 21409

Alexis took care of my fur babies and helped me out with a last minute trip to take care of a sick family member.

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Emily S.
Sitter Profile Image: Louise D.
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Louise D.
from
$28
per night
4.9 out of 5.0 stars
40 reviews
18 repeat clients
6 years of experience
Easton, MD, 21601

Louise left the house tidy and did a great job caring for our pack! We received many photos while away and she was quick to communicate if an issue arose.

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Colleen D.
Sitter Profile Image: Henriette V.
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Henriette V.
from
$65
per night
5.0 out of 5.0 stars
12 reviews
1 repeat client
40 years of experience
Annapolis, MD, 21403

Henri was amazing with our two senior pups, one of which has some issues that required extra attention. She showed all of the love and patience we could have hoped for. It was the first time we left our kiddos with a virtual stranger at our place, but she made it easy by staying in close touch by texting messages and photos. I'd highly recommend trusting Henri with your dogs.

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Beth F.
Sitter Profile Image: Carmel S.
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Carmel S.
from
$55
per night
5.0 out of 5.0 stars
12 reviews
2 repeat clients
5 years of experience
Grasonville, MD, 21638

Carmel was great! She adapted well to my dog’s needs and was very good at keeping us up to date. She took our dog on great long walks, which she loved! Would definitely book again!

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Katarina H.
Sitter Profile Image: Tirzah F.
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Tirzah F.
from
$29
per night
5.0 out of 5.0 stars
2 reviews
10 years of experience
Annapolis, MD, 21403

Tirzah was very attentive and kept me up to date with everything. Sent me videos. I would happily refer her to anyone.

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Pam L.
Sitter Profile Image: Michael P.
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Michael P.
Star Sitter
from
$85
per night
5.0 out of 5.0 stars
70 reviews
36 repeat clients
10 years of experience
Annapolis, MD, 21409

We could not be happier with the care Michael provides to both our girl & our home. The house is cleaner than when we leave & we come home to a tired & happy dog. Michael is also great about communicating & sending pics while he’s sitting for us. 5 stars are not enough!

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Lauri N.
Sitter Profile Image: Catherine J.
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Catherine J.
from
$35
per night
5.0 out of 5.0 stars
4 reviews
1 repeat client
11 years of experience
Annapolis, MD, 21061

Cat was great with Rory! She was very communicative and responsive and we would definitely use her again!

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Jaime D.
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Over 21
pet parents in Chester have booked house sitting

Chester pet parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

Savannah was awesome. We left our two goldens with her for weekend in our home. When we returned everyone was happy! We will definitely use her again

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Ron S.
House Sitting
5.0 out of 5.0 stars

Julie was fantastic! Communicate her arrival, departure, updates on the pups, pictures. Tesla and Eevie were content and happy. Glad I found her; recommended and I will have her watch the pups anytime!

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Josefina P.
House Sitting
5.0 out of 5.0 stars

Taylor did an amazing job taking care of my dog. She responded quickly to my request and kept me updated on my dog while I was away.

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Teresa S.
House Sitting
5.0 out of 5.0 stars

Stacey is Amazing! Will definitely be using her in the future, she made our trip much more relaxing knowing our dogs were being taken great care of.

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Mike C.
House Sitting
5.0 out of 5.0 stars

Brittany was wonderful with my very energetic puppy!! She sent me pics everyday and kept me updated on how he was doing daily. My dog slept on her lap and was very comfortable with her!! I would recommend Brittany to anyone without hesitation. I will be rebooking her for sure!!

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Nancy C.
House Sitting
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Find pet care near you

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 $50

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 4
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 Jan 2026 was about $50 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 Jan 2026, there are 1,004 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, 88% of Chester house sitters respond in under an hour.

House sitters in Chester have an average of 14 years of experience. House sitters with repeat customers have an average of 4 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.