House Sitting in Crestwood

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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Jenna G.
1.
Caring, Flexible, and Trustworthy!Orland Park, IL, 60467
House Sitting, Drop-In Visits, Dog Walking

Jenna was fantastic with our dogs! She stayed with them for a weekend and we had no worries whatsoever. She sent updates and pictures throughout the days, which… (more)

from
$40
per night
Confirmed availability: Memorial day
Rommy P.
2.
WAGGY TAILS INC.OAK FOREST, IL, 60452
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Rommy did a really great job with my pup Betsy while I was out of town. She provided lots of updates which helped me feel very at ease during my time away and m… (more)

from
$50
per night
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Nadia G.
3.
[Insert Dog Pun Here]Clearing, Chicago, IL, 60638
House Sitting, Drop-In Visits, Dog Walking

Nadia stayed with our pup while we were on vacation. We always had updates with pictures and she was wonderful with the communication. Both our girls love havin… (more)

from
$75
per night
Confirmed availability: Memorial day
Andrea L.
4.
Homewood Flossmoor Sitting ServicesEast Hazel Crest, IL, 60429
House Sitting, Drop-In Visits, Dog Walking

Andrea was a great house sitter for our pup over the weekend! She was a great communicator and sent plenty of updates and pictures to ease our minds while we we… (more)

from
$35
per night
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Melissa S.
For the love of pets!Oak Forest, IL, 60452
House Sitting, Drop-In Visits, Dog Walking

Melissa did a great job caring for our felines in our home! We especially appreciated the honest and frequent updates; that means a lot. Our entire brood is lo… (more)

from
$40
per night
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Ready to Take Care of Man's BFFOak Lawn, IL, 60453
House Sitting, Drop-In Visits, Dog Walking

About: Hi, my name is Tiffany and I just graduated from North Central College with my Bachelors in Psychology and Gender & Women’s Studies, with hopes to ge… (more)

from
$45
per night
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7.
Never met a dog I didn’t like!Orland Park, IL, 60462
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Alyssa was a great sitter! She was timely and sent plenty of updates and photos to put my mind at ease while away. (more)

from
$40
per night
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Your 2nd Best Friend's BoardingOAK FOREST, IL, 60452
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Never have I ever seen BOTH of my dogs instantly take to someone the way they did Katrina. My Chow Chow mix is very standoffish until he gets to know you but h… (more)

from
$55
per night
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9.
Pre-vet Student and Dog WalkerOrland Park, IL, 60462
House Sitting, Drop-In Visits, Dog Walking

About: Hello, I am a pre-vet college student with experience in animal behavior and dog training. In high school, I exercised large dogs for friends and fam… (more)

from
$30
per night
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10.
Eager to care for your dog!Evergreen Park, IL, 60805
House Sitting, Drop-In Visits, Dog Walking

Lauren is the only person I know that I would ever recommend for a job. She is responsible, respectful, and trustworthy. I have two dogs that absolutely adore L… (more)

from
$30
per night
Confirmed availability: Memorial day
Patient and compassionateMount Greenwood, Chicago, IL, 60655
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi! I have a fur baby in my family we love dearly, give high fives and fist pumps to. Years ago we had two big dogs at once which was fun and double … (more)

from
$35
per night
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12.
Future VeterinarianChicago ridge, IL, 60415
House Sitting, Drop-In Visits, Dog Walking

About: I am a future veterinarian who has taken care of large and small animals as a veterinary assistant, animal car intern, canine coach, and a dog walker… (more)

from
$25
per night
Dedicated to your dog(s) full time!Oak Lawn, IL, 60453
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Adrienne did a great job managing a multiple pet household that includes pets of almost every variety. She was able to follow the care instructions we left for … (more)

from
$85
per night
Confirmed availability: Memorial day
14.
Afternoon delight weekend B&B for POak lawn, IL, 60453
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kendra is fantastic with my Shih Tzu Lola . Lola loves her always excited to see her. Kendra sends me pictures, they play dress up it's the sweetest.Once Lola g… (more)

from
$60
per night
Confirmed availability: Memorial day
15.
Pets aren’t friends they are familyWorth, IL, 60482
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I believe I’m a excellent fit because I love animals like they were my own children, I consistently buy snacks and treats for my neighbors dog well … (more)

from
$30
per night
16.
Large home with fenced yard/deck.Oak Forest, IL, 60452
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Good morning, On behalf of Debra I’d like to express and give my sincere opinion on why Debra would be a perfect fit for the position she is wanting to fill. … (more)

from
$45
per night
Confirmed availability: Memorial day
17.
Dog lover and a People PleaserMorgan Park, Chicago, IL, 60643
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Andrew care for my 2 dogs great!! I work full time leaving my pups at home for hours. Andrew made sure that my dogs would well care for. He would take them for … (more)

from
$30
per night
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18.
Trustworthy and reliable care🐾❤Midlothian, IL, 60445
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

She is a very responsible person and loves all dogs as her own! She fosters for a rescue and walks, sits and boards for clients. She walked my boxer for 2 years… (more)

from
$40
per night
19.
Amy 
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Dog lover caring the other dogsChicago Ridge, IL, 60415
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Great person overall, super sweet and caring! Great with my pups. Definitely reccomend and will use her again. (more)

from
$30
per night
Fun-filled household for your doggyCrestwood, IL, 60445
House Sitting, Drop-In Visits, Dog Walking

Kimberly does a fantastic job watching Chloe. We get lots of pictures, she always arrives on time, and Chloe seems to really enjoy their time together. (more)

from
$25
per night

Rover also offers House Sitting in:


Never beg a friend to watch your dog again. With Rover, you can find your the perfect Crestwood house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Crestwood who can provide the care your dog needs, when they need it.