House Sitting Chester

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

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Over 9
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: 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

Greetings, I am so grateful to have had Jason and Tracy come stay and care for my precious Fur Babies. Knowing my home and Animals were cared for brought me so much peace of mind to go away and have special time with my extended family. I 100% recommend their services. Thank you Jason and Tracy, I recommend your services to the highest degree! 😊🥰

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Debra C.
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
Star Sitter
from
$30
per night
5.0 out of 5 stars
79 reviews
28 repeat clients
25 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: Lena M.
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Lena M.
Star Sitter
from
$95
per night
4.9 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Chester, 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: Savannah T.
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Savannah T.
from
$50
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
1 year of experience
Stevensville, MD, 21666

Savannah was very punctual for both the meet & greet and the overnight sit at our house. I also appreciated the communication she gave about her schedule. This was our first time having an overnight sitter and it was great to be able to count on someone. Lemonade seemed to enjoy herself as well. We will definitely use Savannah in the future!

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Erin G.
Sitter Profile Image: Alexis B.
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Alexis B.
from
$32
per night
5.0 out of 5 stars
1 review
1 repeat client
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: Wendy B.
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Wendy B.
from
$63
per night
5.0 out of 5 stars
36 reviews
8 repeat clients
54 years of experience
Queenstown, MD, 21658

Wendy is absolutely wonderful! We have several pets and some have complicated care instructions. She did a great job with meds and making sure everyone was taken care of!

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Kristen R.
Sitter Profile Image: Emily B.
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Emily B.
from
$45
per night
4.9 out of 5 stars
27 reviews
10 repeat clients
4 years of experience
Arnold, MD, 21012

We had a wonderful experience with Emily! She communicated with us every day and always sent plenty of photos and updates, which gave us so much peace of mind while we were away. Our dog was clearly loved and very well taken care of, and she treated our home with such care and respect. We highly recommend Emily to anyone looking for a friendly, reliable, and caring sitter, and we would absolutely book with her again!

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Jennifer B.
Sitter Profile Image: Owen K.
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Owen K.
Star Sitter
from
$31
per night
4.9 out of 5 stars
51 reviews
6 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: Shannon M.
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Shannon M.
from
$50
per night
4.8 out of 5 stars
8 reviews
2 repeat clients
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: Courtney A.
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Courtney A.
Star Sitter
from
$80
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
15 years of experience
Edgewater, MD, 21037

Courtney was great! We felt very comfortable being away knowing that our pets were getting so much love and attention. We had clear and frequent communications and a plenty of pictures confirming all the good things happening. We'd (and our critters) would be very happy to see Courtney again.

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Joanne B.
Sitter Profile Image: Alexxis E.
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Alexxis E.
Star Sitter
from
$150
per night
5.0 out of 5 stars
28 reviews
9 repeat clients
15 years of experience
Annapolis, MD, 21409

Alexxis was wonderful with our dog Maddie. She was very communicative with planning and sharing photos/updates and flexible when our drop off time changed and with dropping of Maddie at our home. Would recommend and use again!

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Chelsea K.
Sitter Profile Image: Karen R.
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Karen R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
5 repeat clients
15 years of experience
Annapolis, MD, 21401

Karen took wonderful care of our dogs, Sam and Tito, for a full week while we were on vacation. She was incredibly responsive, always sending updates and photos when we asked, which gave us so much peace of mind. It was clear our boys were happy, comfortable, and well cared for the entire time. She also left our home in perfect condition, which we really appreciated. We would absolutely book with Karen again and highly recommend her to anyone looking for a reliable, thoughtful sitter!

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Julie G.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$75
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

About: Hi, I’m Hannah — a responsible, caring pet sitter who treats your home and pets like my own. I know how difficult it can be to leave your furry family member behind, so I’m here to give you peace of mind with loving, attentive in-home care. Whether your dog needs belly rubs, playtime, medications, or a quiet companion on the couch, I adapt to their unique needs and stick to their usual schedule. I’ll also keep your home tidy and safe so you can return to everything just how you left it (or better!). ~Staying overnight at your home ~Feeding, walks, and potty breaks on your schedule ~Playtime, snuggles, and companionship ~Administering medication (if needed) ~Daily updates with photos and notes ~Light home care (mail, plants, trash, etc.) ~Respectful, clean, and professional behavior in your space Hi! I’m Hannah, a very energetic stay-at-home mom. I can’t wait to welcome your pets into my life! I'm home full-time this summer, so your dogs or cats will get constant attention, affection, and supervision while you’re away. I'm a huge animal lover — patient, kind, and great at following routines. Whether your pet needs playtime, snuggles, walks, or quiet companionship, I'll provide a safe, loving environment that feels like home. Our animals are happiest in their environment with their familiar smells, toys, and routines. I help minimize stress and keep them comfortable while you enjoy your time away, worry-free.

Sitter Profile Image: Josiah S.
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Josiah S.
from
$20
per night
5.0 out of 5 stars
1 review
12 years of experience
Centreville, MD, 21617

About: I will love and take care of your pets as if they were my own. I love to go out and play with pets I care for. I would dog sit when I was in high school for different families. Those families loved how attentive I was, and as a result they would refer me to their friends. I’m always available for you buddies! You and me both know that your pets are more than pets, theyre family. You don’t want just anyone taking care of family. I do currently work full time, however I have a job that is extremely flexible. I set my own hours, including when I am in my office. This pairs perfectly with animal care and house care because I can come and go as frequently as needed. Due to my open schedule I can be available for any needs your pets may have. I prefer to let the client tell me exactly what they want for their pet. I like to keep your life as simple as possible while giving you peace of mind by following any requests you have. If you need your animal crated, if you want them roaming, whatever is asked you can expect to be done.

Sitter Profile Image: maranda c.
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maranda c.
from
$65
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Centreville, MD, 21617

Maranda was fantastic. I really can’t say enough positive things about our experience with her. She was quick to learn and work with the idiosyncrasies of our two cats, took care of our house which was immaculate when we returned and communicated with us while away as much/or as little as we requested. She is very personable, respectful and responsive.

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Stephanie N.
Sitter Profile Image: Michael S.
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Michael S.
from
$35
per night
5.0 out of 5 stars
44 reviews
8 repeat clients
5 years of experience
Dundalk, MD, 21222

I can’t explain how GREAT MICHEAL IS ! Is there was 20 stars I would give it to him. Is the process I also receive the best fall pictures of the girl that Micheal took. If I was you. Book book book !!!

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Dywon F.
Sitter Profile Image: Alexandra M.
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Alexandra M.
from
$90
per night
4.2 out of 5 stars
6 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: Michael P.
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Michael P.
from
$90
per night
5.0 out of 5 stars
74 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

Michael was great. After having to get a later than planned departure, Michael was there to make a smooth transition. He kept in touch with us each day and I felt confident that my Shelties were being well taken care of. I hope to have him back many more times.

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Maureen S.
Sitter Profile Image: Camilla G.
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Camilla G.
from
$85
per night
5.0 out of 5 stars
17 reviews
4 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: Busara C.
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Busara C.
Star Sitter
from
$65
per night
5.0 out of 5 stars
84 reviews
12 repeat clients
5 years of experience
Dover, DE, 19904

Busara was a delight! She gave a lot of feedback on her time with Jasper. Jasper seemed to enjoy having her here. I’d definitely ask her to come another time!

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Lois D.
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The median cost per night for house sitting in Chester is $50

Pet parents share their Rover experiences - Chester

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
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  • 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

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  • 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.

Meet local sitters who will treat your pets like family

  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

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Popular requests for house sitting - Chester

Select a filter and find qualifying sitters offering house sitting.

Sitters in Chester average 4
repeat house sitting clients

FAQs for House Sitting - Chester

Frequently asked questions about Rover

The average cost for House Sitting in Chester on Rover is $50 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 3,331 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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

  • 93% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 95% 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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