Dog Boarding in Winthrop Harbor

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Top rated Winthrop Harbor dog boarders

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: Byron G.
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Byron G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
4 years of experience
Waukegan, IL, 60087

This is the second time we have entrusted Peaches to the care of this wonderful family, and we are just as pleased as the first time—Peaches clearly is as well. We are truly grateful to have found them. Their warmth and attentiveness toward Peaches is remarkable. They are the ideal caregivers anyone could find!!

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Deni R.
Sitter Profile Image: Heather L.
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Heather L.
Star Sitter
from
$35
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
12 years of experience
Kenosha, WI, 53142

Heather and her family were very welcoming ! They allowed Evie and I to come the night before and meet them to make sure everyone was comfortable! Heather communicated and sent so many pictures! The communication and pictures gave me peace of mind while being away. I really enjoyed the little updates! She made sure Evie was comfortable, snuggled, and even helped to get her to eat when she was a bit stubborn! I loved that her and her family loved Evie like their own! I would definitely recommend and would return. Thank you Heather and family❤️

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Jacquis
Sitter Profile Image: Sunshine L.
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Sunshine L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
89 reviews
28 repeat clients
46 years of experience
Kenosha, WI, 53143

Sunshine took a last minute holiday booking and was incredibly flexible! Always great with updates and photos. Best caregiver for my fur baby that I’ve ever received!!

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Zachary Z.
Sitter Profile Image: Kim K.
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Kim K.
Star Sitter
from
$47
per night
5.0 out of 5 stars
81 reviews
36 repeat clients
50 years of experience
Gurnee, IL, 60031

We appreciated the updates letting us know our dog was having a fun time during his stay! Great communication. It always means a lot to know our dog is being well cared for. Already booked a second stay!

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Lorelei S.
Sitter Profile Image: Kim F.
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Kim F.
Star Sitter
from
$56
per night
5.0 out of 5 stars
526 reviews
219 repeat clients
25 years of experience
Kenosha, WI, 53142

I am very comfortable having Kim & her family take care of my dog. Lucy isn't away from us very often and is nervous. I think Kim knows dogs and has the patience to work with her.

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Roxanne H.
Sitter Profile Image: Jennifer A.
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Jennifer A.
Star Sitter
from
$50
per night
5.0 out of 5 stars
74 reviews
34 repeat clients
15 years of experience
Waukegan, IL, 60085

Jennifer was AMAZING with our pup Junie! This was the first time we have utilized Rover.com and we were anxious about leaving Junie with someone we didn't know. Jennifer communicated with me weeks in advance and answered all of my questions. Junie immediately felt comfortable and Jennifer texted me pictures and updates throughout the day, which I LOVED. I highly recommend Jennifer to anyone who needs a super responsible and sweet dog-sitter!!

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Zoey Z.
Sitter Profile Image: Veronique S.
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Veronique S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
23 reviews
5 repeat clients
45 years of experience
WAUKEGAN, IL, 60087

I couldn’t be happier, Veronique was a great sitter. My dogs seems very happy and she took very good care of them. She gave them complementally bath before I picked them up. She sent me photos and videos every day to let me know how they were doing and how they interacted with her dogs and cat. Her house, back porch and backyard are really clean, well taken care of and super nice environment for dogs to run free.

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Kenneth P.
Sitter Profile Image: Nicholaus G.
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Nicholaus G.
from
$60
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
20 years of experience
Zion, IL, 60099

Nicholaus G. took great care of our two dogs while we were on vacation. He provided updates throughout our trip which helped us feel at ease with leaving them with someone new.

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Lisa L.
Sitter Profile Image: Dee S.
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Dee S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
69 reviews
26 repeat clients
60 years of experience
Waukegan, IL, 60085

Dee is incredibly responsive and reliable. She was warm and welcoming at the meet and greet and again when we dropped off Stella at Dee's home. It was nice to get consistent communication and photos while were away, and we appreciate that Dee gave Stella so much attention.

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Beth R.
Sitter Profile Image: Lucy S.
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Lucy S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
45 years of experience
Winthrop Harbor, IL, 60096

This was our first time using Rover and we were pretty nervous because of some of the stories you hear, but after meeting Lucy we felt completely at ease. She is such a kind and genuine person that we instantly trusted her with our St. Bernard Millie. Millie can be semi reactive around other dogs, so knowing that Lucy has experience with dogs like her really eased our worries. Throughout the stay she kept us updated with photos and videos and made sure Millie was happy, active, and well cared for. We will definitely be using her again and highly recommend her to anyone looking for a reliable and attentive sitter.

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Chris K.
Sitter Profile Image: Brianna E.
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Brianna E.
Star Sitter
from
$51
per night
5.0 out of 5 stars
372 reviews
51 repeat clients
8 years of experience
Kenosha, WI, 53143

My pup came back happy, well fed, and well exercised. Brianna and her family were wonderfully kind to my pup and sent lots of photos of fun moments with him! A+++

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Brian M.
Sitter Profile Image: Rachel W.
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Rachel W.
from
$45
per night
5.0 out of 5 stars
6 reviews
8 years of experience
Kenosha, WI, 53142

Rachel was exactly what I needed for my dog. She had open and detailed communication with me the whole time, from booking to pick up. My dog came home happy and healthy. What an incredible weight off while I was out of town to know my girl was well cared for. Would definitely book again.

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Amanda M.
Sitter Profile Image: Kim O.
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Kim O.
from
$65
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
25 years of experience
Winthrop Harbor, IL, 60096

Kim, You are the best! I knew when I picked up Buddy and he didn’t want to leave I found the best sitter for him. I would recommend everyone bring there fury children to you.

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Elizabeth C.
Sitter Profile Image: Taylor G.
Verified Enhanced Background Check
Taylor G.
from
$29
per night
10 years of experience
Waukegan, IL, 60087

About: I have cared for dogs from shelters as well as senior dogs. Now I have a puppy who is 2 years old! I am pretty consistent with giving walks, play time, bathroom breaks, and meals. I also offer transportation services! I have quite a lot of free time as a full time nursing student! I’m outside everyday with my dog! I would love to find some doggy friends for my pup! I have a fenced back yard and a playful friendly dog to keep them company. The house is also dog proof! Dogs are absolutely welcomed indoors! I also have access to a number of outdoor fields for the dogs to play, a beach, dog play areas and more!

Sitter Profile Image: Jacob Miles F.
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Jacob Miles F.
Star Sitter
from
$50
per night
5.0 out of 5 stars
104 reviews
35 repeat clients
10 years of experience
Grayslake, IL, 60030

Jacob made this whole experience so easy, made us feel safe leaving our pet behind while on vacation, and we are confident that our Odie had such a good time! He is passionate about his clients and communicated with us the entire time. I would highly recommend leaving your precious pooch with him and feel great that they are being cared for and kept safe. Thank you Jacob for everything!

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Helen A.
Sitter Profile Image: Celeste G.
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Celeste G.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
13 years of experience
Wadsworth, IL, 60083

We wanted to express our sincere appreciation for your exceptional care of my anxious dog while we were on vacation. It was a relief knowing you kept him comfortable and safe, especially with his anxiety. We also really appreciated you keeping him separate from your cat due to my daughter's allergies – it showed a real dedication to his well-being and consideration for my family. The updates and photos you sent were so reassuring. Thanks again for going above and beyond! Will definitely take Cody back on our next vacation😊

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Shirley P.
Sitter Profile Image: Florence K.
Verified Background Check
Florence K.
from
$42
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
8 years of experience
Wadsworth, IL, 60083

1st time leaving our puppy for an extended period of time (8 days/7 nights). Florence kept us updated with text and videos. She took great care of our baby and treated her like her own. We had a great Spring break and so did our C.C.

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Sheila T.
Sitter Profile Image: Jennifer E.
Verified Background Check
Jennifer E.
from
$40
per night
4.9 out of 5 stars
314 reviews
111 repeat clients
10 years of experience
Lindenhurst, Kenosha, WI, 53143

Thank you so much Jennifer for taking such good care of Fudge. I know you got to know him very well and managed the quirks in his character superbly. I appreciated the regular updates and have no hesitation in recommending you as a great sitter.

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Gillian G.
Sitter Profile Image: Bob and Francine A.
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Bob and Francine A.
from
$40
per night
4.9 out of 5 stars
45 reviews
29 repeat clients
30 years of experience
Gurnee, IL, 60031

Floppy and Ella had a great time! I received updates with pictures almost every day. They were also very accommodating to the pick up and drop off time.

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Nelmarie V.
Sitter Profile Image: Jennifer S.
Verified Enhanced Background Check
Jennifer S.
from
$45
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Beach Park, IL, 60099

I can’t say enough good things about Jennifer! She took wonderful care of my dog, treating them like family. I received regular updates and photos, which gave me peace of mind while I was away. My pup came home happy, relaxed, and clearly well-loved. It’s hard to find someone you can truly trust with your fur baby, but Jennifer went above and beyond. I will definitely be booking again and highly recommend her to anyone looking for a reliable and caring dog sitter!

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Kim J.
1 / 1
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Over 73
pet parents in Winthrop Harbor have booked dog boarding

Winthrop Harbor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Lucy was great with our dog and we were so comfortable leaving our precious baby with her. I believe our dog was a little sad to leave and will miss her until the next time!

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James R.
Boarding
5.0 out of 5 stars

Nice to have people like Nicholaus, Kai was nice with him, calm and loved. I was worried because it was a lot of time out of the city but I saw he was good from the first day. If you need someone to take care of your dog he is your best option.

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Juan Carlos M.
Boarding
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Winthrop Harbor is $50

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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Winthrop Harbor average 13
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Winthrop Harbor is $50 per night, including service fees. Boarding your dog for one week typically costs $350. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winthrop Harbor dog boarding rates can be found as low as $21 to as high as $88 per night.

If you’re searching for a Winthrop Harbor dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 603 sitters provided dog boarding in Winthrop Harbor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 94% of Winthrop Harbor dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Winthrop Harbor have an average of 20 years of experience. Dog boarding sitters with repeat customers have an average of 13 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winthrop Harbor.

Rover makes it easy to find Winthrop Harbor dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 603 dog boarding sitters in Winthrop Harbor on Rover, so you’re sure to find the perfect match for your dog! In Winthrop Harbor, 91% of sitters offer daily exercise, 96% offer medication administration, and 89% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.