House Sitting in Winnetka

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: Jonathan N.
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Sitter Profile Image: Jonathan N.
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1.

Jonathan N.

30+ Years of Pet Care Expertise
Glencoe, IL, 60022
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
65 reviews
10 repeat clients
from
$77
per night

Jonathon did a terrific job house sitting for us and taking care of our two Old English Sheepdogs. Our house was immaculate, and he went the extra mile to clean the sheets and remake the bed. Most importantly though, he took amazing care of our boys which allowed to have a stress free vacation. We will definitely use Jonathon again!

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Sitter Profile Image: Davide A.
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Sitter Profile Image: Davide A.
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2.

Davide A.

Honest, playful, reliable, genuine
Winnetka, IL, 60093
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$105
per night

Davide was fantastic. His motto is “leave it cleaner than I found it” was truly awesome. I’ve had Davide house sit our 130 lbs German Shepherd a couple of times. Max is active and sheds everywhere. He combed him outside, picked up his potties, ran the sweeper and left the mail on the counter. The house was spotless and the dog seemed very happy. Davide sends pictures throughout the day to let you know what your pet is up to and that it is all fine. He texted me a couple of time with questions which I didn’t cover with him - which was great follow up on his part and very professional. I would highly recommend Davide to house sit your pet. He will be house sitting mine again.

Sitter Profile Image: Lucia K.
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Sitter Profile Image: Lucia K.
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3.

Lucia K.

Fun and Responsible Sitter
Evanston, IL, 60201
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$90
per night

Lucia has such a calming effect on Lacey, our little Morkie rescue, while we were away overnight. Lacey did so well with Lucia with her eating and walking regiment. We are very grateful for that.

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Sitter Profile Image: Marisol L.
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Sitter Profile Image: Marisol L.
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4.

Marisol L.

Senior pet enthusiast w flexibility
Wilmette, IL, 60091
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
5 repeat clients
from
$58
per night

Marisol was great! Her second time with our dog and this time for more than a week. She was super considerate of our home and took great care of Ziegler, attending to his quirks and keeping him company while we were overseas. Highly recommend and hope she'll keep watching our pup!

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Sitter Profile Image: Donna C.
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Sitter Profile Image: Donna C.
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5.

Donna C.

Rover 101
Longing for fur on my clothes!!!
Wilmette, IL, 60091
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
390 reviews
111 repeat clients
from
$85
per night

We can't say enough great things about Donna and how she cares for our furry babies! She goes above and beyond. We know they are in the best of care while we are away.

Confirmed availability: Easter Weekend
Sitter Profile Image: Jason A.
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Sitter Profile Image: Jason A.
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6.

Jason A.

Rover 101
Here to keep your furries happy!
Evanston, IL, 60203
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
12 repeat clients
from
$80
per night

Jason stayed with our dogs for a week. I think our pups decided he’s more fun! Jason listened to our needs, was willing to come over to talk and walk through the house, sent photos, and was a great communicator overall. Our house and pups were in terrific shape upon our return. I can’t recommend him enough. Thanks Jason!!

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Sitter Profile Image: Maria B.
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Sitter Profile Image: Maria B.
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7.

Maria B.

animal lover w/ flexible schedule!
Highland Park, IL, 60035
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
16 repeat clients
from
$75
per night

Maria is amazing- went above and beyond with my 6 month old English springer spaniel. She put my dog first the entire weekend. She always exercised him, spent time with him and cared for him like he was her own dog. She sent me photos and updates everyday. Not to mention, she left my apartment absolutely spotless. Her attention to detail with her care of my dog let me feel comfortable and carefree when I was away. You’d be lucky to hire Maria to take care of your pup!! I am so grateful to have found her!

Confirmed availability: Easter Weekend
Sitter Profile Image: Jocelyn M.
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Sitter Profile Image: Jocelyn M.
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8.

Jocelyn M.

Punctual & enthusiastic!
Skokie, IL, 60076
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$50
per night

Thank you for taking care of my pup on my special day!! Thank you for being patient as well 🙏🏾

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Sitter Profile Image: Paige F.
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Sitter Profile Image: Paige F.
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9.

Paige F.

Rover 101
Student with lots of time for pets!
Glenview, IL, 60026
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$75
per night

Paige was outstanding. Her calm demeanor made our skittish dog extremely comfortable. She was great with communication, sending lots of pix of them snuggling. We absolutely would re-book her again.

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Sitter Profile Image: Coty C.
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Sitter Profile Image: Coty C.
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10.

Coty C.

Peace of Mind Pet Care
Evanston, IL, 60201
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
18 repeat clients
from
$80
per night

First time with Coty - came home to happy pets, bedding washed and dishwasher running. We may have to go away more often :) We were able to relax, having great confidence in Coty from her reports and photos.

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Sitter Profile Image: Jackson P.
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Sitter Profile Image: Jackson P.
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11.

Jackson P.

Pets are family!
Glenview, IL, 60025
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
7 repeat clients
from
$100
per night

I can't recommend Jackson enough as a pet caregiver! He is great with animals, really engaging with the dogs and cats that he interacts with. His punctual, and can be relied upon to give pets the attention and care they they need whether it is a walk, check-in, or petsitting.

Sitter Profile Image: Alex H.
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Sitter Profile Image: Alex H.
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12.

Alex H.

Happy dog, from a simple jog
Northfield, IL, 60093
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$75
per night

Alex is sweet and reliable. I give him bonus points because he was willing to come and see my dogs a few times before I had to leave town so that my dogs wouldn’t be anxious. This was major to me cause there were some I interviewed that wouldn’t even do a meet and greet till I hired them. He did a great job and stayed in contact so that I wouldn’t worry.

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Sitter Profile Image: Elliot C.
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Sitter Profile Image: Elliot C.
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13.

Elliot C.

Best Pet Sitter Available
Evanston, IL, 60201
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$30
per night

Elliot did a fantastic job looking after our kitties. He communicated consistently and shared lots of photos. We also really appreciated his flexibility when we had to push our plans back a week due to illness. I highly recommend him.

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Sitter Profile Image: Diana O.
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Sitter Profile Image: Diana O.
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14.

Diana O.

Summer Sitter/Dog Walker
Winnetka, IL, 60093
1.7 mi. away
Boarding, House Sitting
1 review
from
$55
per night

Diana is so loving and good with dogs. She’s caring and responsible. My dog, Brandy can’t wait to see her when she comes by my house. I’d definitely recommend Diana for both dog walking and pet sitting!

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Sitter Profile Image: Jesse G.
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Sitter Profile Image: Jesse G.
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15.

Jesse G.

Cuddles and Care!
Skokie, IL, 60077
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$60
per night

Jesse keeps me so informed on how my pet Finn is doing throughout her stay with him. It's phenomenal!! So many great photos as well!! She is so affectionate and caring with him which is apparent from her communication with me. I feel comforted when she's with him.

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Sitter Profile Image: Claire S.
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Sitter Profile Image: Claire S.
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16.

Claire S.

Pawsitively Devoted Dog Sitter!
Northbrook, IL, 60062
2.8 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$60
per night

Claire was an absolute joy to have sitting for us. Punctual, nice, communicative, friendly and so great with our baby. I would of given her 10* if possible and we would definitely use her again and highly recommend her.

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Sitter Profile Image: Tatiana & Jacob P.
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Sitter Profile Image: Tatiana & Jacob P.
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17.

Tatiana & Jacob P.

Rover 101
Tati&Jake: Furry Friends' Favorites
Evanston, IL, 60201
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
16 reviews
2 repeat clients
from
$99
per night

Tatiana was wonderful and I’ll definitely rebook! She took the time to make sure my dog and I were comfortable and asked lots of thoughtful questions to make sure his needs were anticipated and met. He’s not one to cuddle or walk with new people, and he did both in her first visit. Thanks so much for the kind care, lovely updates and peace of mind overall that my pup was in great hands! ?

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Sitter Profile Image: Viviana F.
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Sitter Profile Image: Viviana F.
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18.

Viviana F.

Your Pets Next Favorite Playmate!
Skokie, IL, 60077
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$70
per night

Wonderful experience! Very professional sitter who took wonderful care of our pets and our house and communicated thoroughly the entire time we were gone.

Confirmed availability: Easter Weekend
Sitter Profile Image: Mike S.
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Sitter Profile Image: Mike S.
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19.

Mike S.

Friendly Dog Lover
Northfield, IL, 60093
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$45
per night

About: I grew up with dogs and have loved dogs and pets my whole like. In my professional career I was a personal assistant to a family who had dogs I am currently open to working just about any days or hours. I take care of my daughters dog occasionally but can find time around that I make sure they are fed on schedule and get plenty of play and exercise. I personally love the outdoors and walking so I will often take the pets outside

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Sitter Profile Image: Ella V.
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Sitter Profile Image: Ella V.
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20.

Ella V.

OBSESSSSED with fur babies!🤩
Winnetka, IL, 60093
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
62 reviews
52 repeat clients
from
$75
per night

We recently used Ella for the first time. During her stay our dog needed immediate care due to a bladder stone blocking his urinary tract. Ella did a great job recognizing the signs, communicating with me, and taking our dog to the ER. We are lucky she was willing to go the extra mile to make sure he received the care he needed.

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Winnetka House Sitting ratings

Overall Rating:
5.0 out of 5 stars

House sitters in Winnetka are rated on average 5 out of 5 stars based on 23 reviews.

Rover also offers House Sitting in:

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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 Winnetka house sitting needs. On Rover, it's easy to find a loving dog sitter in Winnetka 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 Winnetka 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 Winnetka for your dog — people who'll treat him like family.

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