House Sitting in Chester

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Terry S.
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Sitter Profile Image: Terry S.
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1. Terry S.

Rover 101
Pet Mom- Animal and Nature Lover
Waterford, CT, 06385
18.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
78 reviews
33 repeat clients
from
$75
per night

Our pups loved the attention and care Terry gave them. Her communication is outstanding - letting us know when she was leaving, what time she’d return, and notification when she arrived. She sent us daily pictures; updates to how the pups were eating; and doing their business. We were able to vacation without worries! Terry is very highly recommended!

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Sitter Profile Image: Sherry B.
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Sitter Profile Image: Sherry B.
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2. Sherry B.

Animals are therapeutic!
Cromwell, CT, 06416
16.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
85 reviews
25 repeat clients
from
$42
per night

We are so happy that we found Sherry to take care of our 3 dogs! She is polite and responsible and trustworthy. It meant a lot that she really took her time to make sure she knew our babies and their needs before staying with them. My dogs took to her very quickly upon meeting, which was great! We believe our babies were in the best of care! We will definitely continue to use her:)

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Sitter Profile Image: Stephen S.
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Sitter Profile Image: Stephen S.
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3. Stephen S.

Rover 101
Caring & Passionate Pet Sitter
Hebron, CT, 06231
16.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
8 repeat clients
from
$45
per night

Steve is very communicative and responsive! Our pups had a great time with him while we were out of town for NYE. Would definitely recommend him and would book again!

Sitter Profile Image: Kim S.
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Sitter Profile Image: Kim S.
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4. Kim S.

Animal Loving Musician!
Colchester, CT, 06415
11.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$50
per night

She was awesome with our ver anxious dog and left the house looking great. I would definitely rebook!

Confirmed availability: Easter Weekend
Sitter Profile Image: Cayton M.
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Sitter Profile Image: Cayton M.
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5. Cayton M.

Vet Asst, Canine Obedience, Therapy
East Lyme, CT, 06357
13.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
70 reviews
34 repeat clients
from
$85
per night

Cayton not only provided excellent care for our dogs, but also went above and beyond to ensure the safety and well-being of our new home during an incredibly hectic time for us. Cayton’s reliability was a significant comfort. She provided us regular updates and brought peace of mind to an otherwise stressful period. The open and transparent communication from Cayton was truly appreciated. She kept us well-informed about our dogs' well-being and shared reassuring photo updates that showcased their happiness and contentment. Cayton, your exceptional service has made a profoundly positive impact on our move and in our lives. We are sincerely grateful for your dedication and care. Thank you for everything!

Sitter Profile Image: Carolyn C.
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Sitter Profile Image: Carolyn C.
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6. Carolyn C.

What’s life without pets?
NIANTIC, CT, 06357
13.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
12 repeat clients
from
$60
per night

Carolyn was an excellent sitter for our dog Silvie and our kitty cat. I highly recommend her! Carolyn stayed at our home while we were away for one week. She was extremely attentive to our pets and sent us lot of photos and updates so we would not worry. She is excellent with cats as well as dogs and our Silvie just loved her!! Carolyn is an extremely thorough communicator as well. Thanks Carolyn for taking such good care of both of them. We will be in touch soon!!

Sitter Profile Image: Greta N.
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Sitter Profile Image: Greta N.
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7. Greta N.

I will care for your pet as my own!
Killingworth, CT, 06419
4.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
2 repeat clients
from
$50
per night

Greta did well beyond my expectations. My dog is very active and attention seeking. It's a lot sometimes but Greta handled my dog "Hyper" with ease in grace. She sent pictures of them playing and regular updates. I returned to my house just as I left it.

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Sitter Profile Image: Lauren R.
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Sitter Profile Image: Lauren R.
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8. Lauren R.

Every pet is unique 🐾
Old Saybrook, CT, 06475
9.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$35
per night

Lauren was amazing! She housed my Aussie for 4 days and was so great with keeping me update from day to day. My pup also has A LOT of energy and Lauren walked/ played with her everyday! Lauren was super responsive and great with my last minute changes. I would definitely recommend having Lauren watch your fur baby!

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Sitter Profile Image: Diane L.
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Sitter Profile Image: Diane L.
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9. Diane L.

Worked for Ct Humane Society
Cobalt, CT, 06414
12.5 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$64
per night

Diane was available on short notice after another sitter had to cancel last minute and she took amazing care of my senior dog! She went above and beyond, bringing him extra food and treats when he wasn't eating much while we were gone. She left the house neat and our pup didn't miss a beat. Highly recommend!!

Sitter Profile Image: Roger B.
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Sitter Profile Image: Roger B.
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10. Roger B.

Because Pets are FAMILY🐕🐾😁
Westbrook, CT, 06498
5.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
56 reviews
13 repeat clients
from
$75
per night

Roger has been great with a very nervous pit bull mix. I had tried other dog walkers and sitters that have not worked out. Roger is very caring and treats my dog Whiskey like his own. He is calm and patient with Whiskey. I am so happy to have found someone that can take care of him that I trust. He stayed at my house so I could get away and everything went really well.

Confirmed availability: Easter Weekend
Sitter Profile Image: Elizabeth C.
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Sitter Profile Image: Elizabeth C.
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11. Elizabeth C.

Rover 101
Green Witch Gardening and Pet Care
Madison, CT, 06443
10.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
53 reviews
22 repeat clients
from
$75
per night

Beth is so so patient and caring with our old dog and older cat.. they get a lot of love and attention from her!! We’re so fortunate and grateful..🙏

Confirmed availability: Easter Weekend
Sitter Profile Image: Carley T.
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Sitter Profile Image: Carley T.
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12. Carley T.

The best care for your best friend
Westbrook, CT, 06498
8.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per night

LOVE CARLEY! She’s readily available, quick to respond, and most important, my husky loves her! She keeps me up to date on the time spent, along the important “goings on” of my dog. I don’t think that you will be disappointed in the least when hiring Carley!

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Sitter Profile Image: Emily B.
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Sitter Profile Image: Emily B.
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13. Emily B.

Grew up on a farm with many animals
Lyme, CT, 06371
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
8 years of experience
from
$30
per night

About: I have taken care of Cats, Dogs, Horses, Chickens, all kinds of rodents, etc. since I was a kid. Since moving to LA I have taken care of many friends pets both cats and dogs. One of those cats has needed medicine. I am currently working as a freelance production assistant so I have free time to take care of pets. I also grew up surrounded by animals so I love spending time with them. I make sure to follow all instructions you give that you leave. I make sure to not do anything that will make your pet uncomfortable.

Confirmed availability: Easter Weekend
Sitter Profile Image: Gabrielle D.
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Sitter Profile Image: Gabrielle D.
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14. Gabrielle D.

Caring for your pups !
Clinton, CT, 06413
9.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night

This job fits Gabby extremely well considering she is a mother and ongoing pet owner, she is natural with providing a comfortable environment for others. Growing up as a kid Gabby played a major role in my life often times taking on a parent role, that making her a natural care taker very early on. Not only do qualification meet , but the traits that make Gabby is the person you want taking care of your pet!.

Sitter Profile Image: JoAnne B.
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Sitter Profile Image: JoAnne B.
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15. JoAnne B.

Animals ARE Family, not pets
Old Saybrook, CT
8.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$75
per night

Joanne took great care of our senior goldendoodles in our home, she understood their personalities right away and we received daily updates/pictures. I would highly recommend.

Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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16. Sarah C.

Your dog’s new (second)best friend!
Haddam, CT, 06438
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$60
per night

Sarah is by far my first choice when I need a dog sitter for Luna and Roxie. I have relied on her service on several occasions, sometimes even last-minute requests. She always stays in communication with me on a regular basis, which relieves the stress of having to leave my puppies at home whether it is for a day or a week. Above all, Sarah is trustworthy, and our dogs love her. I would be happy to provide personal references upon request.

Confirmed availability: Easter Weekend
Sitter Profile Image: Brooke D.
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Sitter Profile Image: Brooke D.
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17. Brooke D.

Built-in Love For Your Pets!
Chester, CT, 06412
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$50
per night

Brooke has taken care of our chickens for many vacations. She has also taken care of our bunny in the past. She owns or has owned many pets herself, including dogs, a rat , chickens and cats.She is cheerful, responsible and follows instructions so that the animals are always well cared for. I definitely recommend her.

Sitter Profile Image: Nathaniel B.
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Sitter Profile Image: Nathaniel B.
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18. Nathaniel B.

Farm raised, & an avid animal lover
Chester, CT, 06412
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night

He is wonderful with all animals. He has been around and cared for animals his whole life. He works hard and is reliable, can care for any animal.

Confirmed availability: Easter Weekend
Sitter Profile Image: Lauren P.
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Sitter Profile Image: Lauren P.
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19. Lauren P.

Local animal lover
Chester, CT, 06412
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$85
per night

Lauren was very punctual and communicated well. We got updates and photos during the time she was with our pups. She took good care of our home and was very nice! Would definitely rebook.

Sitter Profile Image: Neph W.
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Sitter Profile Image: Neph W.
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20. Neph W.

Animal watch
Deep River, CT, 06417
2.0 mi. away
House Sitting, Drop-In Visits
from
$31
per night

I've known Neph for more than a decade and she has always been a dependable person when it came to watching my dogs while I was away on business. She has a great personality and is a genuine animal lover with a great rapport with pets. In the past I have referred her to other friends and family whenever they needed pets to be taken care of while they were away.

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Chester House Sitting ratings

Overall Rating:
4.0 out of 5 stars

House sitters in Chester are rated on average 4 out of 5 stars based on 3 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Chester:


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.

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