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: Savannah T.
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Savannah T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
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: Jason & Tracy Y.
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Jason & Tracy Y.
from
$28
per night
4.9 out of 5 stars
78 reviews
31 repeat clients
10 years of experience
Stevensville, MD, 21666

Jason and Chloe were a great match! Chloe can be a little hard to handle but Jason did great with her. I know she was well taken care of and loved on while we were away on vacation. I would definately use Jason again!

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Karen P.
Sitter Profile Image: Alexis B.
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Alexis B.
from
$32
per night
5.0 out of 5 stars
1 review
12 years of experience
Grasonville, MD, 21638

About: I have always been an avid animal lover, and have been an active caretaker in my community. Dogs, cats, fish, you name it. I'm happy to take pets on runs/walks, make sure they get plenty of playtime and love, and treats too. I am mostly available on weekends, and occasionally weekdays, inquire and we can work something out together. But can often stop by to let a pet out during the day. I will follow whatever instructions you have and need for the best care of your animal. I will check in with you if you need me too, and make sure everything is done to your liking.

Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$85
per night
5.0 out of 5 stars
19 reviews
5 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: Karen R.
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Karen R.
from
$50
per night
5.0 out of 5 stars
10 reviews
4 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: Bryan J.
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Bryan J.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Chester, MD, 21619

About: I’ve had dogs and cats of all shapes and sizes my entire life, and caring for animals has always been a huge part of who I am. Over the years I’ve owned and cared for many different breeds and personalities, including Saint Bernards, Great Danes, and Coonhounds, which gave me plenty of experience handling large and giant-breed dogs. I’ve also shared my home with multiple cats over the years—many of them seniors—so I understand the patience, routine, and gentle care older pets often need. I’ve spent years fostering animals as well, frequently working with senior pets and dogs that may be anxious or slow to trust new people. I pride myself on being patient and letting animals warm up to me at their own pace so they can feel comfortable and safe while their owners are away. My home currently includes an Alaskan Klee Kai and a Border Collie mix, so daily life already revolves around exercise, enrichment, and making sure dogs stay happy and engaged. When I travel, my trips are often pet-focused—I’ve driven cross-country multiple times with my dogs to explore new trails, parks, and adventures together. For walks, drop-ins, and house sitting, I always aim to keep pets on their normal routine so they feel secure in their own home. As a larger and experienced handler, I’m comfortable managing multiple dogs on leash and adapting to different energy levels—whether your dog loves long walks and playtime or prefers relaxed companionship and a calm presence. I’m also experienced in administering most medications and providing attentive care for senior pets who may need a little extra support. I have a very flexible work schedule, and can accommodate most dogs needs! As far as overnight sitting, I will be there from 8 pm until 8 am and will also be coming by a few times a day. Puppies and youngsters (or whoever needs it!) can be accommodated with more drop ins just let me know! If you require 24/7 care this can be arranged as well just let me know prior to booking! Your dog’s comfort and routine are my top priorities. I provide focused attention, interactive play, and companionship tailored to your pup’s personality — from calm evenings at home to energetic walks or adventures at parks and trails. I’m experienced with all sizes and breeds, so whether your dog is a tiny pup or a gentle giant, they’ll receive care that’s attentive, confident, and consistent. My goal is for your dog to feel safe, happy, and fully engaged throughout their stay

Sitter Profile Image: Wendy B.
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Wendy B.
from
$63
per night
5.0 out of 5 stars
34 reviews
8 repeat clients
54 years of experience
Queenstown, MD, 21658

Wendy was amazing! She was so good with my bully mix who can be wary of others! She took such great care of Luna, and took things at her speed which is exactly what I needed when finding a sitter for my girl! Will definitely recommend and be using Wendy again! Thank you!

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Kaileigh T.
Sitter Profile Image: Emica M.
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Emica M.
from
$50
per night
5.0 out of 5 stars
7 reviews
20 years of experience
Annapolis, MD, 21401

Emica was a wonderful dog sitter for our pups. She gave great updates and took good care of them. I would not hesitate to book her again and can recommend her highly!

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Francesca S.
Sitter Profile Image: Shannon M.
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Shannon M.
from
$50
per night
4.6 out of 5 stars
5 reviews
9 years of experience
Stevensville, MD, 21666

Shannon, Thank you so much for the amazing care you provided for Bentley and Keeper. We truly appreciated the photo updates you sent while we were away; they really helped us feel at ease knowing they were in good hands. We were especially impressed by how respectful you were of our home and how you went above and beyond with cleaning up. It was wonderful to see how affectionate you were with the dogs, allowing them to warm up to you at their own pace. You clearly have a deep understanding of animals, which was so important since they can get quite sad when we leave. You are a truly amazing person and sitter. Thank you again for everything. Best regards, Therese Lewis

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Therese L.
Sitter Profile Image: Carmel S.
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Carmel S.
from
$55
per night
5.0 out of 5 stars
16 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: Taylor M.
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Taylor M.
from
$65
per night
5.0 out of 5 stars
16 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: Cristina M.
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Cristina M.
from
$100
per night
5.0 out of 5 stars
9 reviews
25 years of experience
Stevensville, MD, 21666

Cristina took such great care of our 3 dogs (ages from 2yrs to 15.5yrs!). She sent daily photos and updates and left the house immaculate. Will definitely be using again!!

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Megan C.
Sitter Profile Image: Alexandra M.
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Alexandra M.
from
$60
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
Annapolis, MD, 21409

About: I have worked alongside my mom who has been with Rover for 8 years! I took care of my own dog in my college dorm for a year as well! I’m currently a student at AACC and I’m working on weekend at a restaurant! Most days, I work on schoolwork and hangout with my own dogs at home! I try to take my dog out every hour to two hours because she loves being outside! I try to give her fresh water every few hours and she is feed twice a day! We also go on walks when it’s nice out!

Sitter Profile Image: Owen K.
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Owen K.
from
$31
per night
4.9 out of 5 stars
50 reviews
4 repeat clients
10 years of experience
Severna Park, MD, 21146

Owen was fantastic. Not only was he responsive but the dogs were well taken care of. They were walked, fed, played with, and given a lot of love. While he was watching the pups he also kept the house clean. I got daily pictures ands updates which helped to put my mind at ease about my pups while I was on vacation. I will use Owen again

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John V.
Sitter Profile Image: Julie K.
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Julie K.
from
$50
per night
5.0 out of 5 stars
5 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: Carmella F.
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Carmella F.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Annapolis, MD, 21403

About: I’ve spent my 24 years of life surrounded by dogs and cats as I grew up with a mother who worked in animal rescue. I’ve been around all temperaments and know how to handle the easygoing and the most reactive. I also have experience with puppies and plenty of experience with senior pets as most of my own dogs are seniors. I currently live with my 3 cats and 1 chinchilla! I currently work full time however besides those 8 hours a day I am free to care for and look after your pets! I’m available everyday of the week including weekends and am committed to prioritizing your pets. When it comes to caring for pets, safety is always my top priority. In your home, I follow your pet’s established routine as closely as possible. I’m vigilant about locking doors, securing gates, and following any specific safety instructions you provide. I also monitor your pet’s behavior to ensure they’re healthy and comfortable. During drop-ins, I check on your pet, refill water and food as needed, and give them attention and playtime. I make sure doors and windows are locked when I leave and always follow any safety guidelines specific to your home, such as alarm codes or gate instructions.

Sitter Profile Image: Bohdanna G.
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Bohdanna G.
from
$30
per night
5.0 out of 5 stars
75 reviews
28 repeat clients
25 years of experience
Stevensville, MD, 21666

Always fantastic! My Jasper gets lots of attention, lovin' and nice walks. Bo takes care of him like he was hers....and is the perfect house sitter!

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Madeline D.
Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$50
per night
15 years of experience
Queenstown, MD, 21658

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.

Sitter Profile Image: Brooke F.
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Brooke F.
from
$45
per night
5.0 out of 5 stars
76 reviews
17 repeat clients
10 years of experience
Chester, MD, 21619

We know our dogs are in great hands with Brooke when we’re away! Great communication! Thank you so much for taking such great care of our girls!

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Lauren B.
Sitter Profile Image: Mary L.
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Mary L.
from
$120
per night
4.9 out of 5 stars
35 reviews
15 repeat clients
30 years of experience
Stevensville, MD, 21666

About: My family & I been around & cared for kitties & puppies for 20+ years. I’ve personally owned chickens & rehabbed bunnies & squirrels. My fur family is extremely important to us & we pledge to care for your pets like our own. We have a fenced in backyard and plenty of domestic pet care experience. Currently I’m a full time homemaker and have lots of time to spend quality time with your fur babies. Occasionally my husband Brandon helps with Rover duties. He is awesome with both animals & people! If needed I have the ability to separate my pets & yours. I can administer medicine including injections with proper instructions. Ask me about brining in mail, watering plants, garden care, farm animal care, & light cleaning. Call my Rover number to receive my personal cell phone Having extra puppies around the home is easy & we can offer long potty breaks in our fenced in backyard as well as a daily walk! The home & yard are secure & your fur babies will be safe with us. Please let us know if your pup tends to run/escape!

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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 stars

Savannah is awesome. We have used her for both drop ins and house sitting. Our golden retrievers live her. See sends daily updates and pictures. When we come home house and dogs are perfect t and happy!

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Ron S.
House Sitting
5.0 out of 5 stars

Cristina took such great care of our 3 dogs (ages from 2yrs to 15.5yrs!). She sent daily photos and updates and left the house immaculate. Will definitely be using again!!

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Megan C.
House Sitting
5.0 out of 5 stars

Alli was awesome! We had to be at a rehearsal dinner and wedding and we were from out of town with no idea what to do with our dog, Henry. We were so lucky we could depend on her!

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Jeff J.
House Sitting
5.0 out of 5 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 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 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
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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 Jun 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 Jun 2026, there are 1,016 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 15 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.