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: jilian t.
Verified Enhanced Background Check
jilian t.
from
$32
per night
15 years of experience
east lyme, CT, 06333

Jilian was great! She came for a meet-and-greet and Mozzie loved her. She kept us up to date throughout her stay and gave him his medications as indicated. There was an issue with a “cost adjustment” that she helped us resolve—really appreciated the help. Great experience!

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Liz M.
Sitter Profile Image: Shannon E V.
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Shannon E V.
Star Sitter
from
$60
per night
5.0 out of 5 stars
25 reviews
7 repeat clients
6 years of experience
Marlborough, CT, 06447

Shannon always goes above and beyond with our pups. She keeps us updated with frequent photos and messages, and really goes the extra mile to make sure they are well taken care of. She stayed at our house for a week with them, and really put us at ease while we were away. We love (and the pups love!) having Shannon watch them!!!

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Lauren G.
Sitter Profile Image: Jessica W.
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Jessica W.
from
$40
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
25 years of experience
East Lyme, CT, 06357

Jessica was very attentive to our 13 yr old dog, making sure he was well fed and got his multiple medications. She kept us updated with videos and photos. He was happy to see us when we got home but I think he also missed Jessica!

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Catherine D.
Sitter Profile Image: Mark W.
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Mark W.
from
$32
per night
4.5 out of 5 stars
2 reviews
8 years of experience
Westbrook, CT, 06498

Mark and his fiancé stayed with our 8 month old puppy, 9 year old dog and our cat for 5 nights in our home. We couldn’t have been happier with his care. He sent daily updates, pictures, and videos. He is clearly an animal lover. Our home was well cared for and he shoveled the driveway after an unexpected snow storm. I was completely able to enjoy my vacation without a worry. I highly recommend Mark for in home pet care.

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Nancy H.
Sitter Profile Image: Brianna E.
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Brianna E.
from
$80
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
7 years of experience
Chester, CT, 06412

Thank you so much. We always feel safe leaving our animals and home in your care. Definitely recommend you to friends and family.

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Rebecca M.
Sitter Profile Image: Sophia A.
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Sophia A.
from
$60
per night
5.0 out of 5 stars
7 reviews
10 years of experience
Portland, CT, 06480

Sophia was truly amazing. She communicated every step of the way and always reached out with any questions. I appreciated how consistently she kept me informed with updates and photos, and how she let me know when she arrived and left each day. She also gave me helpful summaries of their daily activities so I always knew how Kharma was doing. I came home to a neat and tidy house, the trash taken out, and a very happy dog. It was clear Kharma was well cared for. I’d absolutely trust her again.

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Nunu F.
Sitter Profile Image: Kristen M.
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Kristen M.
from
$60
per night
45 years of experience
Killingworth, CT, 06419

About: I’ve had dogs my whole life and absolutely love being around animals. I’ve also worked as a dog and cat sitter, helping with walks, feeding, drop-ins, and overnights. I’m very reliable and pay attention to the little details so your pet feels comfortable and cared for. I have experience with puppies and senior dogs, can help with basic puppy training, and am comfortable giving medications if needed. I treat every pet like they’re my own and always try to make it a fun, positive experience, whether that’s a good walk, playtime, or just extra cuddles. I have a flexible work schedule and am able to fit pet care easily into my day. I’m available for walks, drop-ins, and some overnights (around my kids schedules), and make sure pets are cared for on a consistent schedule. I’m reliable and always plan ahead so your pet gets the attention and routine they’re used to. I always follow the owner's instructions closely, make sure collars/leashes are secure, and pay attention to any specific needs or behaviors. I’ll also keep you updated so you know your pet is safe, happy, and well cared for while you’re away. On walks I always pay attention to my surroundings to keep your dog safe. I'm not there to pay attention to your beloved dog, not get distractes by my phone or anything else.

Sitter Profile Image: Kim B.
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Kim B.
from
$75
per night
5.0 out of 5 stars
47 reviews
23 repeat clients
30 years of experience
Haddam, CT, 06438

Kim was awesome. She had a great attention to detail and asked questions to make sure Abby was well taken care of. She kept in contact while we were away. This was great as we did not worry at all! She also made sure our fish and chickens were cared for as well!!

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Karen M.
Sitter Profile Image: kathryn s.
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kathryn s.
from
$50
per night
5.0 out of 5 stars
13 reviews
4 repeat clients
10 years of experience
East Lyme, CT, 06333

Kathryn took great care of our 2 beagles while we were away. I know they'll miss her. She even swept up(they are messy) and cleaned off the kitchen counters. We would definitely request her again, in fact we already did.

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phmurph@sbcglobal.net
Sitter Profile Image: Palma T.
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Palma T.
from
$55
per night
5.0 out of 5 stars
31 reviews
5 repeat clients
25 years of experience
Norwich, CT, 06360

We don’t like to leave our boy home alone if we’re going to be gone longer than a couple hours. Palma graciously came and hung out with him at our house, and everything worked out great! Thank you!!

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Sarah D.
Sitter Profile Image: Delaney H.
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Delaney H.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
18 years of experience
Deep River, CT, 06417

Delaney went above and beyond for our dog during our weekend away. She provided updates, asked questions, and called with concerns, which allowed us to trust that everything was well underway and cared for in our absence. She left the house very clean.

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Nora B.
Sitter Profile Image: Vincent G.
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Vincent G.
Star Sitter
from
$75
per night
5.0 out of 5 stars
63 reviews
18 repeat clients
10 years of experience
Clinton, CT, 06413

Fantastic pet sitter! Vincent took amazing care of my dog providing updates and lots of walks and affection. Paula directions exactly will definitely be using again

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Jalena B.
Sitter Profile Image: Jessica J.
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Jessica J.
from
$88
per night
30 years of experience
Chester, CT, 06412

About: I've cared for so many kinds of pets for folks...They trust me to care for them when away and feel relaxed to do them! I will care for many kinds of pets for people in need of a kind, loving genuinely interested in your pet safety, attention, feeding, walking, and everything in between! They are my daily routine! Dedicated to the job! I am open to working whenever I am needed for pet care and home care! They can feel safe with me! At home I have a fenced in yard for my dog, my sister's dogs, and we work this out very well. At others homes, i am mindful of their needs through whatever means the owners have for the pets and act accordingly.

Sitter Profile Image: Kimberly G.
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Kimberly G.
from
$100
per night
5.0 out of 5 stars
8 reviews
1 repeat client
25 years of experience
Durham, CT, 06422

Kimberly has a beautiful energy that the dogs responded well to. I could tell from the photos she sent that they were having a fabulous time playing with her. When I got home they were safe and sound and relaxed...and even a bit tuckered out, which was perfect considering I'd had a long day!

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Robin C.
Sitter Profile Image: Faith L.
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Faith L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
47 reviews
7 repeat clients
14 years of experience
Groton, CT, 06340

We really appreciate the good care from Faith for our pup Theo. She was prompt in responding, always conscientious, and everything went very smoothly while we were out of town.

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Scott M.
Sitter Profile Image: sharon b.
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sharon b.
from
$75
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Old Saybrook, CT, 06475

About: I’ve been a dog lover my whole life and have always had dogs in my life. As an adult, I’ve trained 3 of my own dogs. I own my own home in a quiet neighborhood which I share with my brother and my 4 year old boxer Bette. My home is near many great walking areas I am a runner; and I walk with or without my dog regularly. I am patient And tolerant, but not a pushover, and I can offer your pet a very nice experience in my care I have a very flexible schedule so I can be available at many different times of the day. I can do pet sitting g at your home during the day or overnight My dogs have always been considered part of the family and I am very affectionate with my fur babies and you can expect the same from me with your furry friends

Sitter Profile Image: Rebekah P.
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Rebekah P.
from
$50
per night
10 years of experience
Montville, CT, 06370

About: Hello! I am Becky, I'm an Eastern Connecticut local whose been watching my friends, family, and acquaintances dogs and cats for 10+ years. I have given care to elderly dogs who had special needs and ran with young pups who need the exercise! I'd love to learn what you're looking for and see if I am the pup sitter for you. I do all the services provided on this website. I have two cats who love to meet new animals! Message me to learn more and book a meet and greet! I only work 1st shift Wed.-Fri. at my day job, so I have lots of time to give your fur babies attention! Lets set up a meet and greet and we can talk about what your pets needs are! If I am pet sitting in your home your fur baby will get lots of attention because of my limited work schedule. I'll take your dog(s) for walks daily. Dogs and other pets will get plenty of play time! I can cater to whatever needs your pet has! If you are boarding your dog(s) at my home I live on a quiet street great for walking dogs. I have two friendly cats at my house and a few roommate who can give extra attention while I'm at work during the day Wed.-Fri. Your pets will rarely be alone!

Sitter Profile Image: Christine V.
Verified Background Check
Christine V.
from
$65
per night
4.9 out of 5 stars
210 reviews
87 repeat clients
15 years of experience
Middlefield, CT, 06455

Christine was fantastic! We have five cats that she watched for us on short notice while we were out of town over the weekend - two of the cats are special-needs and need medication, and two of the cats are fosters that required special handling. Christine did a great job handling the medication and special care of all of our cats, and she texted me photos and updates regularly!

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Rachael D.
Sitter Profile Image: Ariana W.
Verified Enhanced Background Check
Ariana W.
from
$40
per night
10 years of experience
Groton, CT, 06340

About: I had a maltese puppy for 10 years from age 9 weeks onward and most recently had a shih tzu puppy that turned 1 on 5/28/25. In the oast I've had pets including hamsters, guinea pigs, chickens, and fish of my own. I work from home and have a flexible schedule, so your pup will get lots of attention and care throughout the day. Here's what a typical day looks like when your dog is with me: 🐾 Morning (7am–10am): Potty break, breakfast, and a light walk or play session 🐾 Midday (11am–2pm): Walks, potty breaks, enrichment games, or just relaxing cuddle time 🐾 Afternoon (3pm–6pm): Another walk or active playtime in a safe, calm environment 🐾 Evening (7pm–9pm): Dinner, a final potty break, and winding down for the night I'm available for: ✅ Drop-in visits ✅ Dog walking ✅ Puppy care Weekend and holiday availability included! I’m happy to accommodate special routines, medications, or specific instructions your dog needs to feel comfortable and loved. When you trust me to care for your dog, I show up with love, respect, and attention to detail — all in the comfort of your dog’s familiar surroundings. 🐶 In-Home Peace of Mind: I care for pets in their own homes, where they feel most secure. Whether I’m dropping in for a quick visit, taking your pup for a walk, or staying overnight, I follow your routine closely to minimize stress and keep your dog calm and happy. 🦴 Personalized, Gentle Care: I specialize in small breeds and have over 10 years of experience. From meal schedules and potty routines to medication or calming techniques, I provide care tailored to your dog’s specific needs. 🚶🏽‍♀️ Safe & Engaging Walks: Walks are done one-on-one in familiar areas, with close attention to your pet’s energy level, leash behavior, and comfort. I avoid crowded dog parks or risky environments to keep your dog safe. 📝 Trustworthy & Transparent: I communicate clearly, provide updates, and send photos during every visit. You’ll always know how your pet is doing, whether I’m there for 20 minutes or staying the night. Your pet stays safe, your home is respected, and you can relax knowing your furry family member is in loving, responsible hands.

Sitter Profile Image: Sitara A.
Verified Enhanced Background Check
Sitara A.
from
$50
per night
8 years of experience
Madison, CT, 06443

About: I'm who you call when your dog needs to run around and tire themselves out, or when your cat needs to curl up with someone in the sunlight! I grew up taking care of my lovely cockadoo Otis, as well as going on runs with my step-family's energetic black lab and golden retriever. In the years since, I've taken care of dogs and cats of all ages and breeds. I love learning every pet's specific needs, schedule, and energy levels. Excited to meet you and your furry friend exactly where you need! I'm currently working remotely as a writer, so I'll have plenty of time for your pup or your kitty. My schedule is usually quite flexible, and unless I'm out of town, I can make last minute calls work! My own dog was a rescue from the streets of New York City, and we worked very hard to slowly build trust with him, to the point he became the most affectionate dog I've seen! So even if your animal is skittish, I will happily mind their boundaries while showing them all the love I can. I also prioritize an animal's safety above all else, and am extremely attentive to what mischief your pet might be getting up to.

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Over 13
pet parents in Chester have booked house sitting

Chester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Delaney went above and beyond for our dog during our weekend away. She provided updates, asked questions, and called with concerns, which allowed us to trust that everything was well underway and cared for in our absence. She left the house very clean.

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Nora B.
House Sitting
1 / 1
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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 $60

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 Apr 2026 was about $60 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 Apr 2026, there are 736 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, 87% 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.