House Sitting in Chester

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Kaitlyn F.
Never a dull moment with me around!Clinton, CT, 06413
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Kaitlyn house sat and watched our dog cooper while we were out of town for our wedding! We are helicopter dog parents and she kept us completely at ease, sendin… (more)

from
$30
per night
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Sarah M.
2.
Nurse who loves dogs : )East Lyme, CT, 06333
House Sitting

Sarah is the embodiment of a dedicated, attentive, hardworking, and caring dog sitter. When she watched my sweet dog Fiona for a week, I could tell Fiona was ha… (more)

from
$30
per night
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Charlotte H.
I love dogs more than anything!Killingworth, CT, 06419
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Charlotte did a great job walking and sitting our dog. She sent us cute pictures of Tessie as she went, which was comforting. (more)

from
$35
per night
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Christine V.
CHRISTINE'S FUR BABIES PETCAREMiddlefield, CT, 06455
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I have used Christine several times. She is always reliable and my Fur Baby loves her. She also sends comical pictures and texts that make me laugh. Who else… (more)

from
$40
per night
Samantha S.
Excuse me, can I pet your dog?Old Saybrook, CT, 06475
House Sitting, Drop-In Visits, Dog Walking

Patrick had a great time with Samantha! It was the first time he had been away from us, and she made him (and us) feel right at home. She has well-trained dogs … (more)

from
$60
per night
Confirmed availability: Memorial day
6.
I will love them like my own.HIGGANUM, CT, 06441
House Sitting, Drop-In Visits, Dog Walking

Thea did such a great job with our pups! She was super responsive, provided a ton of updates and pics (which we loved!) and was overall fabulous! I would highly… (more)

from
$85
per night
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Pets are familyColchester, CT, 06415
House Sitting, Drop-In Visits, Dog Walking

Heather house sat and looked after our two dogs Sadie and Lizzy and our cat Neo over a a three day weekend. She was wonderful. Dogs were very happy with their… (more)

from
$30
per night
Confirmed availability: Memorial day
Pro Pet Sitter w Extra Insurance!Old Saybrook, CT, 06475
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Adriana and Chris were absolutely incredible! They came and did a very thorough interview and meet & greet with the dogs. While I was away they took great care … (more)

from
$75
per night
9.
Affection for your fur baby! 🤍Old Lyme, CT, 06371
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I am a 24-year-old girl who loves animals. I have my own little baby pup, Rosie, who is 7 months old. She is the first dog that I ever owned, but I h… (more)

from
$80
per night
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10.
Forever Friend for your Fur FamilyMiddletown, CT, 06457
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I cannot say enough good things about Kelsey. She is so personable & friendly. She seems to have a connection with my pup, that no matter the distance between v… (more)

from
$75
per night
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Freelancer with SAFE OPENYARD/care!Deep River, CT, 06417
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Alexander is a very kind, gentle, smart, trustworthy young man. I have had him take care of my dogs several times and have been very satisfied with the conditi… (more)

from
$24
per night
Confirmed availability: Memorial day
Madison’s Pampered Pet RetreatsMadison, CT, 06443
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Hands down, Mary-Ellen is the best dog sitter I have had the pleasure to work with. She is a very loving and caring pet sitter. My maltipoo, Spence, always thor… (more)

from
$60
per night
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13.
Experienced, reliable, pet lover!Middletown, CT, 06457
House Sitting, Drop-In Visits, Dog Walking

Emily has cared for my dogs and cat numerous times. I appreciate the daily updates that she gives me on how they are doing and how she obviously loves animals. … (more)

from
$25
per night
14.
Trustworthy Animal LoverNiantic, CT, 06357
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Shannon is a dog person to the core. She enjoys raising them, nurturing them and loving them. She has taken my dog in many times and he is well cared for and lo… (more)

from
$40
per night
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15.
Frequent hiker!Ivoryton, CT, 06442
House Sitting, Drop-In Visits, Dog Walking

Jenny took great care of our two dogs while we were away, provided lots of photos to update us on how they were doing! We came home to two happy dogs, which mak… (more)

from
$25
per night
16.
Home full time - large fenced yardEast Haddam, CT, 06423
Dog Boarding, House Sitting, Doggy Day Care

I have known Peter for over 40 years. Peter is the most compassionate, loving, loyal person. Peter has a contagious fun loving spirit whom always sees the posi… (more)

from
$45
per night
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Animals are lifeWestbrook, CT, 06498
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I am happy to give a excellent review for Christine B.She is the most caring and patient person I know. I have learned also from her for help with my Cat, Jaspu… (more)

from
$45
per night
18.
Your dog and I will be soulmatesOld Saybrook, CT, 06475
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Emily is an extremely responsible, kind, and caring person. She loves dogs so much, I have never seen her smile so much until she sees a dog. She cares for her … (more)

from
$35
per night
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19.
Amy 
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Loving, Caring and AttentiveWestbrook, CT, 06498
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi my name is Amy. I have been petsitting for 15 plus years. I have two pups of my own a jack russell mix and a lab mix. They love having new play ma… (more)

from
$40
per night
20.
Full-Time Animal AdorerDeep River, CT, 06417
House Sitting, Drop-In Visits, Dog Walking

About: Similar to us all, I have a passion for animals. I have been surrounded by pets my whole life and continuously find any excuse to hang out with our f… (more)

from
$40
per night

Rover also offers House Sitting in:


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Chester house sitting needs. On Rover, it's easy to find a loving dog sitter in Chester who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Chester house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Chester for your dog — people who'll treat him like family.