House Sitting in Chester

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

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.

1 / 1
Sitter Profile Image: Kat H.
Verified Enhanced Background Check
Kat H.
from
$75
per night
5.0 out of 5 stars
32 reviews
12 repeat clients
10 years of experience
Deep River, CT, 06417

Kat did a wonderful job! Our dog loved her, and we received lots of photos and updates throughout our trip. As an added bonus, the house was spotless when we got home. Highly recommended!

Profile image
Emily S.
Sitter Profile Image: Kristen M.
Verified Enhanced Background Check
Kristen M.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
45 years of experience
Chester, CT, 06412

We are so happy with Kristen as a sitter for our 2 pups! She is experienced, attentive, and professional. Our dogs and house were in perfect form when we got home, and our dogs were not stressed at all. We look forward to using her regularly and having peace of mind when we go away.

Profile image
Lara G.
Sitter Profile Image: Jessica W.
Verified Enhanced Background Check
Jessica W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
12 reviews
6 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!

Profile image
Catherine D.
Sitter Profile Image: Dina C.
Verified Enhanced Background Check
Dina C.
from
$40
per night
5.0 out of 5 stars
3 reviews
15 years of experience
East Lyme, CT, 06357

Wonderful experience....thank you so much for watering the plants and bringing in the mail.

Profile image
Joseph M.
Sitter Profile Image: Serenity M.
Verified Enhanced Background Check
Serenity M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
3 years of experience
Essex, CT, 06426

About: I’ve worked on farms and worked with multiple animal types from dogs to goats. I’m accustomed to schedule planning and checking everything off each day and night. I am open in the afternoons and I work in the early mornings. I am quite flexible as long as I have prior notice. I do work a full time job aswell. I have a very relaxed home as I have my own puppy and she has full ranged of the entire apartment. She is fixed and potty trained.

Sitter Profile Image: kathryn s.
Verified Enhanced Background Check
kathryn s.
from
$50
per night
5.0 out of 5 stars
14 reviews
5 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.

Profile image
phmurph@sbcglobal.net
Sitter Profile Image: Lauren V.
Verified Enhanced Background Check
Lauren V.
from
$45
per night
1 year of experience
Chester, CT, 06412

About: To be honest, when I was a child I had a deadly fear of dogs. That was until my mother forced me to go to exposure therapy (yes she made me go to a club where they sat you with over ten dogs. Here, I fostered a love for them, and learned a lot about them. They need activity and they also need rest. They need a lot of attention but they reciprocate with fierce loyalty and unwavering love. I would love to help a family continue to give their dog the attention it deserves so they can also live their lives! I am a new college graduate looking for a full time remote position. The job market is competitive and I expect to be unemployed for at least a couple months. I have full time availability and will always have weekends. Let me help full time workers right now while I am figuring out life! My anxious dog requires a lot of attention and ensuring comfort. He gets lots of outdoor time and plenty of exercise in the morning, lunch, and night. He is fed twice a day with a mix of dry and wet food. I work on his tricks with him at least once a day! I also have cared for cats throughout my whole life. Fostering kittens, feeding them, cutting and administering pills for my disordered baby! Additionally brushing my animals, playing with them, and knowing when to give them space. I love my animals and have spent my life ensuring their care!!

Sitter Profile Image: Sophia A.
Verified Enhanced Background Check
Sophia A.
from
$60
per night
4.6 out of 5 stars
12 reviews
1 repeat client
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.

Profile image
Nunu F.
Sitter Profile Image: Mark W.
Verified Enhanced Background Check
Mark W.
from
$65
per night
4.7 out of 5 stars
3 reviews
1 repeat client
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.

Profile image
Nancy H.
Sitter Profile Image: Shannon E V.
Verified Enhanced Background Check
Shannon E V.
Star Sitter
from
$60
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
6 years of experience
Marlborough, CT, 06447

Shannon was absolutely amazing! We felt completely at ease during our vacation, knowing our dogs were in excellent care. She provided frequent updates and photos, which we truly appreciated. Our house looked just as we left it.Our house was exactly as we had left it. I highly recommend Shannon as a sitter; we’re so glad we found her!

Profile image
Rachel K.
Sitter Profile Image: Renana M.
Verified Enhanced Background Check
Renana M.
Star Sitter
from
$100
per night
5.0 out of 5 stars
125 reviews
54 repeat clients
40 years of experience
Old Saybrook, CT, 06475

About: I've rescued and taken care of Animals for as long as I can remember and will care for your pets as if they’re my own. Please schedule drop offs and pick ups between 6 am and 6 pm. If you cannot pick up by 8 pm please book a sleepover. There’s a dog door that leads to the fenced back yard. I go outside with them to make sure they are safe. My home is only 600 sf so it’s easy to see everyone at all times! There are plenty of cozy spots for your dog to relax.

Sitter Profile Image: Sierra J.
Verified Enhanced Background Check
Sierra J.
from
$40
per night
5.0 out of 5 stars
1 review
1 repeat client
15 years of experience
Old Saybrook, CT, 06475

About: I've taken care of aniamls since I was 3, I take of my friends and neighbors animals, to give feed them and walk them and bathe them. I don't work because I live on a small farm and take care of them and all my dogs and birds and cats and I can work with anyone's pets after school. I have a dog fence with a doggy door for in and out and it's all fenced in and I have very friendly dogs that will Play and keep company.

Sitter Profile Image: Nikki B.
Verified Enhanced Background Check
Nikki B.
from
$60
per night
4.9 out of 5 stars
20 reviews
8 repeat clients
6 years of experience
Middletown, CT, 06457

Nikki was terrific with my kitties as I was out of town for 8 days. She delivers and additionally left my home in tip-top shape. My cats were very well taken care of and calm upon my return. I could not ask for more.

Profile image
Lori S.
Sitter Profile Image: Charles D.
Verified Enhanced Background Check
Charles D.
from
$32
per night
5.0 out of 5 stars
1 review
40 years of experience
Chester, CT, 06412

About: Retired police/military K9 handler who has spent a significant time in his professional career enforcing animal cruelty laws. Wide range of experience with all types of dogs and cats. I currently work a full-time job enforcing animal cruelty laws. Nearing retirement in July of 2027 I am available in early morning hours as well as evenings Monday thru Friday and anytime on weekends and holiday's. It is important to know your animals. They tell us when they are happy, sad and ill. Paying attention to the signs they give you is vital to a safe environment. Constant communication between the owner and myself is a pivotal step to ensuring these signs are not overlooked.

Sitter Profile Image: Kimberly G.
Verified Enhanced Background Check
Kimberly G.
from
$100
per night
5.0 out of 5 stars
9 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!

Profile image
Robin C.
Sitter Profile Image: Sitara A.
Verified Enhanced Background Check
Sitara A.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
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.

Sitter Profile Image: Cayton M.
Verified Enhanced Background Check
Cayton M.
Star Sitter
from
$110
per night
5.0 out of 5 stars
135 reviews
58 repeat clients
10 years of experience
East Lyme, CT, 06333

Cayton was lovely. My dog was nervous on a rainy windy evening and she was so patient and calming with him. She went above and beyond to keep him happy and engaged.

Profile image
George S.
Sitter Profile Image: Liz K.
Verified Enhanced Background Check
Liz K.
from
$65
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
27 years of experience
Middletown, CT, 06457

Liz was absolutely fabulous with our (very large!) golden, Cutiepie! While I was initially nervous with our very first petsitter/housesitter, I ended up ecstatic that we had such a lovely person to play with and care for Cutie and look after our home while we were out of town. We received regular photo and text updates, and I was quickly notified about any questions she might have about Cutie's needs. Liz herself has such a wonderful, friendly, and easy going manner about her as well; I felt immediately comfortable with her in my home and with my dog (who has now adopted Liz as her BFF and already misses her!). House was tidy when we returned and Cutie was happy, calm, and clearly well cared for. I'll definitely be booking Liz again next time we need to leave Cutie at home alone! Thank you Liz for being the perfect companion to Cutie while we were away! Couldn't have asked for a better petsitter! <3

Profile image
Rebecca H.
Sitter Profile Image: Matthew R.
Verified Enhanced Background Check
Matthew R.
from
$32
per night
50 years of experience
Old Saybrook, CT, 06475

About: I’ve shared my life with both cats and dogs since I was a youth. I am equally comfortable with tiny lap dogs and large, powerful breeds. I understand the different energy levels and handling requirements each size needs. Whether your pet is a playful pup or a senior cat who prefers a quiet companion, I adapt my care to fit their unique personality. My schedule is highly flexible, allowing me to make pet care a top priority throughout the week. I am currently available for dog walking, drop-in visits, and house sitting, ensuring your pets receive consistent attention and exercise. My routine is built around being present and active, so you can rest assured your animals are getting the dedicated care they deserve. Safety is my absolute priority. During visits and walks, I maintain a vigilant eye on your pet’s surroundings and behavior. I ensure all doors and gates are securely locked upon entry and exit, and I always double-check that water bowls are full and the environment is hazard-free before I leave. I provide frequent updates and photos so you can see firsthand that your pet is safe, active, and happy. I treat every animal with the same care and attention I give my own two dogs.

Sitter Profile Image: Jasmine D.
Verified Enhanced Background Check
Jasmine D.
from
$75
per night
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Waterford, CT, 06385

Jasmine was great and helped us out in a pinch this weekend. She sent a couple pictures and was responsive to our questions and comments! We definitely would hire her again!

Profile image
Sarah P.
1 / 1
View more sitters

Over 14
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.

Profile image
Nora B.
House Sitting
1 / 1
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 $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 Jun 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 Jun 2026, there are 700 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, 90% 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.